sailboat charter maine

Explore, Discover The Ocean

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine and Northern New England.

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Enjoy The Ocean With Your Family

NorthPoint Yacht Charters offers a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

• How To Charter

Charter with NorthPoint Yacht Charters

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events. We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free.

About NorthPoint Yacht Charters

Welcome to the 2024 Charter Season

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine, Northern New England and the Canadian Maritimes. We offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events.  We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free. 

Announcements

Luxury yachts.

Select from wide variety of boats including both power and sailboats 20-80 feet:

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Defiant Morgan 43 43‘

Osprey Hinckley Pilot 35 36‘

Andromeda Sabre 30 30‘

Lucky Dog Sabre 36 36‘

Sweetness Cape Dory 36 36‘

Coconut Grand Banks 40 40‘

Wind Dancer Gulfstar 44.5 45‘

Thira Catalina 30 30‘

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What Customers are Saying...

KOAN performed beautifully. …. The engine runs great . MC

Our charter of Blue Goose two was excellent. She is the only boat I have ever charter or used including my own that there was nothing to fix. She was very clean, well outfitted with towels, linens and basic condiments.

We had a great cruise on Alliance. We visited Pulpit, Castine, NE Harbor, Seal Harbor (Vinalhaven), Islesboro and Tenants. RE

Get In Touch With Us

NorthPoint Yacht Charters arranges sailing and power boat cruising charters, we offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

• Crewed Charters
• Experience Resume
• Charter Resouces
• Charter FAQs

Check out our newest sail the Hurricane Island Aquaculture Experience

A Morning in Maine

Sailing tours on beautiful penobscot bay, featured sailing trips.

• Most Popular!
• Users All Ages
• Clock 2 Hours

2-Hour Sailing Trip

The best way to get a taste of the Maine coast! Sail out of Rockland Harbor past the breakwater lighthouse on your way to Penobscot Bay and the rugged coastal islands.

• Users Ages 11+
• Clock 9.5 Hours

Hurricane Island Aquaculture Experience

Join us for an exclusive opportunity to visit the Hurricane Island Center for Science and Leadership (Hurricane Island) aboard Morning in Maine!

• Clock 6 Hours

Monroe Island Adventure

Your island adventure awaits! Maine has over 3,000 miles of coastline, and almost half of that is on islands only accessible by boat.

• Clock 3 Hours

Science under Sail

Join us and a science educator from our partners at Herring Gut Coastal Science Center in Port Clyde as we set sail to learn about the ecology of Penobscot Bay!

Day Sails on Penobscot Bay

Enjoy the Maine Coast’s beauty from the deck of Morning In Maine. Relax and watch the seabirds and harbor seals as the ketch glides through the waters of Penobscot Bay… or lend a hand in sailing the boat!

On most Maine sailing trips we see Rockland Breakwater Lighthouse, Owls Head Lighthouse, and historic schooners. Monday morning is the best time for a day sail in Rockland, Maine, where we watch the schooners sail out of the harbor for their week-long cruises.

We look forward to having you aboard!

The boat accommodates 21 passengers and can fill up quickly, so make your reservations early!

#1 Outdoor Activity in Rockland, Maine! Our Customers Love Us!

Maine is best by sailboat.

“Loved our afternoon on Morning in Maine. The wind was great and the boat is really lovely. Capt Tyler and George were great crew. Saw eagles, a harbor seal and all the sights you’d want to see in Rockland. Sailing really is the best way to get to know Maine.”

Best "boat ride" in Maine

“As Mainers, we have had the opportunity to go on various “boating adventures” along the Maine coast. This was the most pleasant and fun one ! 2 hours was perfect. The captain allowing the kids to help with the sails was very cool and even steer… Totally made their day. The captain was very personable and made the trip interesting. I was concerned about getting seasick, but the ride was actually very smooth.”

“We had a wonderful time on our sailing expedition and learned a lot about the area. Definitely worth the time to spend some time on the water with folks that live in the area sharing lots of good stories.”

Great experience!

"Our sail on a Morning in Maine was one of the highlights of our trip. The views were beautiful and the ride was smooth and relaxing. It was a great experience and one that I highly recommend!"

EVENING STAR YACHT CHARTERS

Maine Bareboat Yacht Charters

Sail the Coast of Maine on a Beautiful Classic Sailboat

Looking to charter a bareboat yacht on the coast of Maine?   Evening Star   is a 45' traditional sailboat available for bareboat charter from Belfast Harbor in the heart of Penobscot Bay!   The yacht Evening Star is equipped with Hood Stowaway roller furling masts and has two double staterooms, each with its own head and shower.  

Now Taking Reservations for 2024      Available Bareboat or with Captain

207.415.9698

SEAGLASS SAILING CO.

We're Not Just Better, We're the Best

S/V Seaglass, a 1965 Pearson Rhodes 41 turns heads everywhere she sails.  

The 41' masthead sloop can comfortably accommodate up to 6 passengers for 1/2 day, full day, and overnight voyages around Casco Bay.  

A comfortable cabin and spacious cockpit provide gracious space for relaxing and entertaining.  

Captain Paul Leddy, who grew up sailing the waters of Casco Bay, is looking forward to helping you plan an unforgettable Maine Experience.  

Contact us today, or learn more about voyages aboard S/V Seaglass .  

Inspired Work

Get in Touch

Captain Paul and Seaglass Sailing Co. are here to share the beauty of Casco Bay and a passion for sailing with all of their visitors. Questions, comments or special requests? We’d love to hear from you, so don’t hesitate to reach out today.

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We happily offer private sailing charters for up to 6 guests and all occasions. One flat rate covers the cost for our boat and the efforts of our captains for any of our four regularly scheduled departures. Customized times are often available so don’t hesitate to ask.

Please read on to learn more about what sail camden is all about and feel free to call, text or email with questions, unsure about booking, read our rave trip advisor reviews.

Call or Text: (207)230-9340

Click here to read more about the Heritage Rebuild and our sailing vessel Inherit the Wind!

Offering Crowd-Free Private Sailing Charters

Experience the intimacy of your own private sail aboard a beautiful classic on one of our regularly scheduled charters or a customized adventure . *six passenger maximum per united states coast guard regulations*, we sail four times daily from beautiful camden maine. our trips are always private to your group creating an intimate atmosphere with you, your friends or family, and our licensed captains who are eager to share an adventure with you on the penobscot bay, regularly scheduled private daysails.

Fun, Friendly & Affordable!

"couldn’t have been a more perfect sail the heritage is a beautiful boat; it is obvious that the owners love her. taylor, our captain, was so personable, knowledgeable, and capable—he made our sail outstanding. judy (the owner with her husband) is just a delight we can’t say enough about this cruise, this company, this captain, this boat just do yourself a favor and go", dreaming of boat ownership or maybe just want to show off some seamanship skills to your friend with a boat perhaps you are just curious about the mechanics of sailing or always eager to learn something new well sail training with our experienced captains and their undivided attention could be just the thing for you , now offering sail training.

Looking for something different? We love helping guests create customized sails aboard Heritage whether it be a half or full day charter, island adventure or special event. Shoot us an email to start planning your sail now. * $150 per hour with a 4 hour minimum.

Customized crowd-free charters, extended sails, island adventures & more, "epic sailing trip yesterday to warren island with sail camden., captains jeff & taylor’s witty narratives kept us informed and entertained on our custom picnic trip love this sailing option out of camden- flat rate for 1-6 people to sail for 2-3 hours, or opt for private custom trip as we did- great staff willing to work and make sure your sailing adventure is awesome. highly recommend having the boat all to yourselves", we pride ourselves on our customer service., please, reach out with any questions.

Thanks! Message sent.

Our 37th Year in Camden!

Celebrating our 105th anniversary 1918-2023, on the national register of historic places, schooner surprise.

Book Online Now!

Day trips :

Join us for a two hour daysail on the elegant Schooner Surprise out of Camden, Maine. We sail around the magnificent Penobscot Bay. On our Camden day cruises we will see lighthouses, wildlife, private yachts and summer estates. We offer Sunset sails, Tuesday night Sunset sails with live music, Full moon sails and Fireworks sails. We sail 7 days a week from mid May to mid October. Get involved and help raise sails or steer the boat, we are great with kids! Come and join us for a cruise on board the most famous windjammer in Maine. We offer environmentally friendly boat tours. We have limited amount of passengers with cushioned seating for all. Come sail the Maine Coast with us.

See our schedule and rates

Private Charters :

Join us for your Camden Maine Charter on the Schooner Surprise. Special events, weddings, birthdays, family reunions, anniversaries and corporate  events. Two hour, half day and full day cruises on the beautiful coast of Maine. Have us cater your Camden cruise and serve exquisite appetizers on a sunset sail or a lobster lunch. Our Maine windjammer cruises will give you an unparalleled view of Camden Hills. We have been highly rated tour operators in Camden Maine for 35 years. Rated #1 on Trip Advisor!! Book your Camden Charters with us.

Learn more about private charters on the Schooner Surprise

Special Events

Full moon sail with live music.

Watch the sunset over Camden Hills and the full moon rise over Penobscot Bay.

June 21 (7:15pm - 9:15pm) July 20 (7:15pm - 9:15pm) August 18, 19 (7:15pm - 9:15pm) Rate: Adults $65 / Kids $47

September 17 (5:30pm - 7:30pm) Rate: Adults $65 kids $50

Fireworks over Camden Harbor

July 4 7:15pm - 9:15pm Rate: Adults/Kids $76

September 30 7:30pm - 9:30pm Rate: Adults/Kids $75

Sunset Sail with Live Music

Watch the sunset over Camden Hills and listen to live acoustic music.

July 1, 3, 5, 8, 10, 12, 15, 17, 22, 24, 26, 29, 31 (7:15pm - 9:15pm)

August 2, 5, 7, 9 (7:15pm - 9:15pm)

August 12, 14, 16, 19, 21, 23, 26, 28, 30 (5:15pm - 7:15pm)

September 4, 12, 14 (5:15pm - 7:15pm)

Rate: Adults $71 / Kids $62

Birding and Marine life tour with ornithologist Richard Podolsky

July 2, 3, 4, 9, 10, 11, 16, 17, 18, 23, 24, 25, 30, 31 (10am - 12pm)

August 1, 6, 7, 8, 13, 14, 15, 20, 21, 22, 27, 28, 29 (10am - 12pm)

Rate: Adults $65 / Kids $60

Contact Us:

Schooner Surprise Ramiro and Nicole de Acevedo Ramos 207.236.4687 1 Bay View Street Camden, ME 04843

[email protected]

Sloop Anjacaa

Check out our sister ship: Sloop Anjacaa

Camden Rockland Maine  Chamber of Commerce Camden, Lincolnville, Maine Inns, B&B’s and Hotels Rockland, Rockport, Maine Inns, B&B’s and Hotels Vacation Rentals Camden Maine Weather Schooner Surprise Trip Advisor Schooner   Surprise Facebook Page Schooner Surprise Yelp Schooner Surprise Instagram Down East Magazine Maine Magazine Penbscot Bay Pilot Web News Maine Boats, Home and Harbors website

The Sailing Yacht BLUE VAYU

Your Captain Linda Hanson

Capt. Linda Hanson is the owner and operator of BLUE VAYU. She holds a 100-ton license. Linda has cruised and raced sailboats on the Atlantic Ocean and the coast of New England for the past 30 years. In her opinion, Penobscot Bay offers spectacular sailing and is the jewel of the Maine coast. 

As a former teacher of French and Spanish, Hanson has traveled extensively in Europe and South America. Sh

Sail beautiful Penobscot Bay on your own private charter. Come aboard BLUE VAYU and discover the adventure and the beauty of a well-balanced yacht under sail.  The Blue Vayu is a classic Swedish sloop built in 1974 and extensively restored to display her mahogany and teak topsides.  Her classic European design and graceful demeanor turn heads wherever she goes.

Your private charter is $150. per hour with a two hour minimum. The fare is for parties of up to six people. Snack and beverage is provided.  

Custom excursions

Custom excursions are between two and six hours. Trips between two to three hours allow ample time to sail to inner harbor lighthouses and  observe the lobstering culture. Longer excursions may visit nearby islands and harbors.

* weather permitting

Photo Gallery

Captain Hanson on a day trip to Pulpit Harbor, North Haven Island, Maine with sailor and extreme skier Dan Egan.

Husband and wife comment on their three day trip to Mt. Dessert Island

Set sail aboard Blue Vayu and improve your sailing skills with Captain Linda Hanson

1 Harbor Park, Rockland, Maine

207-749-1289

[email protected]

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Maine Yacht Charters

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Featured Yachts in Maine

WAYFINDER | From US$ 375,000/wk

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MAINE (USA)

The USA’s Maine coastline is best explored by yacht; and a Maine yacht charter is the most convenient way to achieve this. It extends for more than 3,400 miles making it larger than the Californian coast. There are more than 4,613 islands along the coastline just waiting to be explored. A mega yacht charter vacation off the coast of Maine, offers the perfect combination of tranquility and adventure. There are picturesque coastal towns and quaint lighthouses dotted along the shore. During your voyage keep an eye out for seals, migrating whales and porpoises. 

Why not begin your itinerary from DiMillo’s Marina in Portland? It’s a great city for entertainment, nightlife and shopping as well as having a fully serviced marina. There are many restaurants here to dine in before setting off on your superyacht journey. Set sail for Monhegan Island which is 1.4 miles long and 0.7 miles wide. Only ten miles out to sea, the island has several hiking trails, exquisite “fairy houses” not far from Penobscot Bay. Ask your captain to drop anchor off Hurricane Island which once had a thriving community due to quarrying. Visit Castine, home of Maine’s Maritime Academy and other marine related industries. 

Maine has an intriguing rocky coastline, lots of maritime history and nature areas such as the Acadia National Park. No trip to this park is complete without seeing Thunder Hole. It’s a landmark with stunning views, high rocks and a small cavern at the bottom of the inlet. When waves hit the rocks and release air, thunderous booms can be heard. It shows how powerful the ocean can be with the waves reaching 40 feet in height, nature at its best. You’re sure to get wet so remember to take a waterproof. In Baxter State Park, there’s Mount Katahdin and the Appalachian Trail along with plenty of wild moose. You will also see beautiful sandy beaches and lobster shacks.

Take a cruise to Butter Island, a firm favourite with superyacht charter guests for its spectacular beaches. Anchor in Penobscot Bay before setting off to Nubble Beach to enjoy a swim. If you’ve got the energy, climb up to the top of Montserrat Hill where you can take in magnificent views of the Camden Hills and Mount Megunticcok.

Blue Hill Bay lying to the west of Mount Desert Island in Hancock County, Maine, is very popular with recreational boaters. Here you can also tuck into local delicacies like crab, lobster, salmon and mussels. The town of Blue Hill at the far end of the island offers a great chance to buy local handicrafts and souvenirs. Maine is gaining in popularity with luxury yacht charter enthusiasts so do include it as part of your vacation itinerary.

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New England

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Maine Yacht Charter Enquiry

A great place to find info about a yachting vacation in Maine ...

Yachting Destinations In and Around Maine

In close proximity to Maine are a number of exciting sailing destination.

Yachts for Charter in Maine

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Queen miri | from eur€ 1,125,000/wk.

AVALON | From US$ 155,000/wk

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Gulf Islands

Alaska & British Columbia

Florida Keys

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Casco Bay Custom Charters

Embark on an unforgettable journey: customizable private boat charters & tours of casco bay, celebrating a decade on the water.

Experience Casco Bay’s Splendor with Our Private Boat Charters & Tours. 

At Casco Bay Custom Charters, we invite you to explore the captivating beauty of Maine from the unique vantage point of our classic wooden vessels. For the past decade, we’ve shared more than just boat tours. Our charters are personal introductions to the coastal landscapes, lighthouses, and culinary delights that define our region. 

With a focus on customization, each voyage with us is tailored to uncover the genuine essence of Casco Bay, enhanced by our commitment to exceptional service. Led by experienced crews passionate about sharing their knowledge and love for Maine, we ensure your journey is not only enjoyable but truly memorable.

SEARCH CHARTERS BY GROUP SIZE

Designed for exclusivity, our charters accommodate intimate groups of up to 6 guests or larger gatherings of 7-16. Our friendly captains and knowledgeable stewards ensure a personalized boating experience.

Small Groups aboard MONHEGAN

Intimate cruises for up to 6 on a vintage lobster boat

Learn More »

Large Groups aboard MARIE L

Classic coastal tours for up to 16

DINING CHARTERS

The best way to eat locally-sourced Maine cuisine is aboard our Dining Charters. Specialty menu dining charters, chef’s dinner sunset cruises, and bottomless mimosa brunch cruises available. Local catering and all-inclusive drink upgrades are available aboard EVERY Casco Bay Custom Charter!

Private Sunset Dinner Cruise

Small Groups (up to 6 guests) aboard MONHEGAN

Bottomless Mimosas & Croissant Brunch

Large Groups (7-16 guests) aboard MARIE L

ELOPE ON A PRIVATE ISLAND

Experience the magic of saying ‘I do’ on a private island with our Fortland Elopement Package. Escape to Fortland for an intimate, and unique wedding ceremony set against the backdrop of a stunning coastal landscape. An unforgettable way to share your vows and begin your new adventure in love

FORTLAND ISLAND ELOPEMENT PACKAGE

Unique, intimate wedding ceremonies on Fortland.

SAIL WITH GLEAM

For a limited-time, we’re partnering with GLEAM to offer sailing charters off the coast of Maine. GLEAM is a fully restored vintage 12 meter yacht that hosts up to 13 guests. Each captivating sailing excursion includes captain and crew for an effortless Maine summer sail.

GLEAM Private Sailing Charters

Sailing Excursions along Maine's Coast

CREATE YOUR OWN CUSTOM CHARTER

Tailor any of our curated tours and experiences for your group’s needs, from corporate bleisure to family-friendly outings and celebrations. Collaborate with our team to craft your perfect day, selecting from diverse food, beverage, and tour itinerary options. Your bespoke Maine adventure awaits.

Unforgettable 5-Star Maine Experiences ⭐⭐⭐⭐⭐

Embrace authentic maine with casco bay custom charters.

Journey with us and unlock the essence of Maine on our signature boat tours. Enjoy the serenity of coastal cruises while indulging in gourmet locally-sourced food and craft beverages. Our classic wooden vessels offer a truly authentic Maine experience for unforgettable memories.

Eager for an unparalleled experience? Book your private boat charters and coastal tours to navigate the beautiful waters of Casco Bay!

Set Sail in Boothbay Harbor

Experience the coast of maine.

There are those who endeavor to live, to find bright spots in their lives and seek refreshing opportunities.   Sailing rarely disappoints.   Spending a couple of hours cruising the New England waters on a bright sunny day is fresh, restorative and comforting; all for $50.

“Capricia” is berthed at the Carousel Marina, across the harbor  from town  at 125 Atlantic Ave ,  where an elegant meal at the Whales Tale Restaurant or a boat side lobster bake on the docks will provide the ultimate coastal Maine experience.  Learn more about the Carousel Marina here: www.carouselmarina.com

There are those who endeavor to live, to find bright spots in their lives and seek refreshing opportunities.   Sailing rarely disappoints.   Spending a couple of hours cruising the New England waters on a bright sunny day is fresh, restorative and comforting.

Unique Scenery

Take in the iconic rocky coastline of Maine with Captain Dave and get a taste of what makes this place so special.

Picturesque Landscapes

Boothbay Harbor and midcoast Maine are home to many of Maine’s most dramatic oceanfront properties and natural wonders.

Working Waterfront

Boothbay Harbor serves are the ideal hub for your visit to coastal Maine; with shopping, dining, and endless recreational opportunities.

Unforgettable Experience

Join us for a romantic day cruise, a family outing, a group retreat, or even a solo sail trip on the waters of Boothbay Harbor.

Our Cruises

Book a cruise.

Sail Capricia with Captain Dave aboard his classic Alden sailboat on a 2-hour cruise around the bays and islands of Boothbay Harbor, Maine.

Let’s Get In Touch

©2024 Sail Capricia . All rights reserved. Site by Adventure Advertising .

Dump out your bucket list.

This is the adventure you’ve been looking for..

Windjamming is, quite literally, like nothing else on Earth. By turns exhilarating, relaxing, surprising, and nurturing, it’s like no other vacation you’ve ever experienced.

Wake up to the quiet solitude of Maine’s coast, find renewal in the wind and sun, and surprise yourself as you help steer the ship. Aboard our vessels, with itineraries tossed to the wind, our guests find both a spark of adventure and time to reflect.

Is there a sailor in your soul?

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world.

When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of safety and quality. As your captain and guide they will treat you to honest, heartfelt Maine hospitality and personalized attention.  Explore our fleet and offerings to find your perfect cruise.

The Windjamming Experience

Simply put, windjamming is about reconnecting with our essential enjoyment of life. It’s about gorgeous scenery, human connection, soul-nourishing meals, and taking time for both adventure and reflection. Our playground is the sparkling sea and the spruce-clad granite islands that rise from it.

Whether you join us for a three-night cruise or a week, we promise you a total escape from the ordinary. Be prepared to get closer than you ever have before to breathtaking wildlife like eagles, seals and porpoises, to visit some of North America’s most spectacular coastal scenery, charming villages and unspoiled islands, and to savor the freshest, fire-cooked Downeast fare. With only 16-31 guests on our ships, you’ll experience the kind of honest, heartfelt hospitality that keeps our guests coming back year after year.

Welcome to the only place in the world where schooners play in abundance. Where steady breezes, glittering bays, and literally thousands of islands make Penobscot Bay one of the most revered cruising grounds on earth.

On our small ship cruises, we have complete liberty to explore secret anchorages, remote fishing villages, and charming gallery towns. Schooners have been an intrinsic part of the Maine Coast for centuries, and there is something very special about rounding the point and arriving at anchorage under sail. Come touch this culturally distinct, pristine and physically breathtaking part of America.

Explore by Schedule

Use our cruise finder below to explore sailing options that fit your schedule. If your dates are flexible, or you just want to learn more, visit our fleet page and each vessel’s website. Reservations can be made directly with the Windjammer of your choice. Have fun exploring! Whichever vessel you choose, you are sure to have the sailing adventure of a lifetime.

Find My Trip

It was a super trip. Beautiful ship, thrilling when under sail. Two gorgeous days and two rainy ones that didn't diminish the experience... relaxing in the cabin and in the galley chatting (and on deck watching the coast go by in the rain.) Excellent food at every (very generous) meal. Friendly crew, friendly passengers... all in all, a wonderful experience.

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

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Southern Maine

June - October 

Offering 2 hour group sails, and 3-6 hour private excursions out of Saco, ME.  Sail along the rocky Maine coastline while spotting minke and humpback whales, porpoises, seals, bald eagles and Atlantic sunfish. Host your own private cocktail party!  Feel like a kid again and jump off of the bows of the boat into the warm Saco river and float with pool noodles.

Saco is perfectly located 20 minutes from Kennebunkport and 20 minutes from Portland.

2 hour sail:  $125 pp

Sail out of the mouth of the Saco river, past the historic Wood Island lighthouse and through Biddeford pool.  Look for seals, porpoises, sturgeon and minke whales.  If it is windy or wavy that day, no problem!  We will cruise up the gorgeous Saco river instead, where you can view bald eagles, sturgeon, osprey, blue herons, and egrets.

Private sails: starting at $750

Rent the boat privately for your excursion!  We cater the day specifically to your desires, including time of day, how long we sail, and the activities.  Trip options include sailing along the beautiful rocky coast of Maine, cruising down the lush marshland of the Saco river, or a mixture of both. Incorporate a swim stop in the river, or just cocktail and cruise with the sun on your face.  The day and boat are yours to enjoy!  Private sails include a captain and crew, so you can enjoy every moment in luxury.

You can book online here through the "book now" button or call or email for private bookings and special events and inquiries.  Private sail start times are typically 10am, 1pm, and 5pm but can be adjusted per your request.

We are located at the Camp Ellis Pier, at 5 Bay Ave, Saco, ME 04072.  Before your charter, park in the Camp Ellis pier parking lot.  You will have to purchase a parking permit at the machine in the center of the lot.  Look for our sign, walk down the dock and the S/V Liberty will be waiting for you!  We board 5 minutes prior to departure.

To book a trip, ask for a price or for other inquiries, please

call  +1-571-334-7885 , or send us an email to  [email protected]

When the weather is warm, there isn’t any better place to enjoy yourself than gliding through the glassy waters of the Casco Bay during a boat charter in Portland, Maine. Sail Portland Maine is here to give you a personal boating experience unlike any other! Our day trips take you through the harbor, where you’re likely to see some of the diverse wildlife, historic structures and lighthouses, breathtaking coastal islands, and much more.

Our Unique Boat Charters in Portland, Maine

We offer two-hour public or private chartered trips with several trip options for you to choose from throughout the day or evening.

Choose your Perfect Casco Bay Trip

Meet our boats, eleanor hawkes (sailboat) → book a trip on the eleanor hawkes.

The Eleanor Hawkes has space for a group of up to 6 people , making it one of the smallest chartered cruises in Portland – and thus, one of the most crowd-free and intimate experiences on the harbor!

• 12:00 PM – 2:00 PM : $85 per Person/$500 Private Charter
• 3:00 PM – 5:00 PM : $85 per Person/$500 Private Charter
• 6:00 PM – 8:00 PM  ( Fall hours vary ): $85 per Person/$500 Private Charter

Calista Ann (Classic Motor Yacht) → Book a Trip on the Calista Ann

Our Classic Motor Yacht, the Calista Ann, is the perfect picnic boat. It has space for up to 12 guests to keep that intimate experience but also allows you the space to enjoy your own beverages and snacks.

All charters on Calista Ann are private no matter how many people are in your party. If your group would like more than 2 hours, additional rates apply(Call to book extra time). Please contact us or call directly  for any questions.

• 12:00 PM – 2:00 PM : Private Charter starting @ $720
• 3:00 PM – 5:00 PM :   Private Charter starting @ $720
• 6:00 PM – 8:00 PM (Fall hours vary): Private Charter starting @ $720

Sunsets in Portland, Maine can also be pretty incredible, which makes our sunset cruise at Sail Portland Maine a no-brainer! Whether you’re a hopeless romantic wanting to share a special evening with your significant other (or even having thoughts of proposing!) or a group simply looking to enjoy the show, a Casco Bay sunset will give you an experience that is second-to-none.

Book Your Cruise with Sail Portland Maine!

Make the most out of the summer season with the best boat charter in Portland, Maine. Whether you’re visiting from out of town, planning a unique, intimate event, or simply spending time with loved ones, let us provide you with the best possible chartered boat experience. For a memory you’re sure to reminisce about for years to come, book your trip with us at Sail Portland Maine today!

Book Your Trip with Sail Portland Maine

Ellis Boat Charters

Maine bareboat charters & boat rentals – midcoast & downeast maine, the wilbur 42 heads to lunt harbor, frenchboro.

LOCATION: Lunt Harbor, Frenchburo, Maine

VESSEL:  “NENA” – Wilbur 42 Flybridge Cruiser

NARRATIVE: After an excellent briefing on the twin-engined Nena, we ran up Somes Sound for an overnight stay on a mooring provided by Abel’s Lobster Yard. The next morning we made our way in heavy fog to Frenchboro. After hopping onto a ball in the tight Lunt Harbor, we hung out on the dock as the Lunt family processed their lobster catch. The Lunt family couldn’t have been nicer – they described their business, their history, and their newest sugar kelp venture. We ate at the Lunt Deli and ordered lobster dinner which we took back to the Nena to enjoy the spectacular sunset dinner. After 3 days of hanging out in Lunt Harbor, we made our way back to Dysarts Marina (just in the nick of time as the fog rolled back in). We were content to stay in our slip, read a good book aboard the Nena, and cook wonderful meals with local produce and delicious Maine blueberries. Shane Ellis and his crew were wonderful hosts. Their hospitality is genuine and we enjoyed every moment.

Day trip to Stonington & Isle au Haut

VESSEL:  “Ariel’s Song” – Wilbur 38 Flybridge Cruiser

NARRATIVE: It was the perfect day! Our group of 12 thoroughly enjoyed the boat, the excursion, and our captain! Hands down, it was the favorite activity for everyone! We can’t wait to book it again soon!

Atlantic Nationals and Lobster Rolls

LOCATION : Blue Hill for the Atlantic Nationals 2023

VESSEL:  “Hathor” – Ellis 36 

PHOTO: Atlantic Nationals in Blue Hill 2023 – Christine Guinness Photo

INSIGHTS: The only chafe was forgetting to ask about the night setting for the plotter – User error. And I w ish I had woken up earlier to get around to Brooklyn and Swan’s Island.

Heading Downeast in an Ellis 36 Express

NARRATIVE: After over 30 years of chartering sailboats this was the first time chartering a power boat. It was a very happy experience. We were checked out by Troy and Brian who prepared us extremely well on all aspects of the boat. The boat itself was in perfect shape and fully supplied with fresh sheets etc. We strongly recommend Ellis Boat Charters.

PHOTO: Hathor at its pickup location – Dysart’s Marina – with a rather ominous shipwreck in the background. 

To Roque Island and back with a Hinckley Picnic Boat

LOCATION : Roque Island, Maine

VESSEL:  “Lab Adore” – Hinckley 36 Picnic Boat

PHOTO: Roque Island – roughly 40 nautical miles from Southwest Harbor (up the coast – or “Downeast” if you wish). 

INSIGHTS: For the trip to Roque Island, I recommend hiring a captain even if one is moderately experienced. One might want to give greater emphasis when training a renter on the need to regularly clean it out of seaweed from Hinckley’s jet drive.

Three Days with a Wilbur 38 Flybridge Cruiser

LOCATION : Various Locations around Southwest Harbor departing from the Claremont Hotel

NARRATIVE: We had three great days aboard Ariel’s Song, doing day trips with two wonderful skippers, Mike and Christian. We had one passenger with mobility issues, and Mike and Christian, along with the great dock crew at the Claremont Hotel, were incredibly sweet and helpful with her. There are many great spots in that area to cruise, go ashore for lobster lunch, and anchor or moor for a swim. The water up in Somes Harbor was 65 degrees warm, which was considerably better than out in the open water, and we borrowed a mooring and had a glorious swim in that tranquil spot, surrounded by pretty boats, in clean clear water.

PHOTO: Wilbur 38 “Ariel’s Song” at the dock in Southwest Habor

Ellis Boat Charters – a top notch organization

VESSEL:  “No Altitude” – Ellis 28 Express

Finding a Maine Gem on our Ellis Charter

LOCATIONS : Eggemoggin Reach, Buck’s Harbor, Castine, Camden, Stonington, Billing’s Yard, & Bass Harbor 

VESSEL:  “Hathor” – An Ellis 36 Express Cruiser

Afternoon Cruise from The Claremont Hotel

VESSEL:  “Downeaster” – An Ellis 36 Express Cruiser

NARRATIVE: Shane at Ellis is super responsive and he set up a great day for us. The boat was spacious and had a nice swim platform off the back. We toured around the Southwest harbor and other harbor areas for the afternoon – very pretty.

PHOTO: The Claremont Hotel   – located at the entrance to Somes Sound in Southwest Harbor. Their Moorings, Dock, and launch services make this the ideal place to land when not out on your Ellis Charter vessel. The Claremont Hotel offers wonderful dining experiences at the Little Fern restaurant and Batson River Fish Camp (at the boathouse on the dock). 

Day Trips with a Hinckley Picnic Boat

LOCATION :  Southwest Harbor

VESSEL:  “Lab Adore” – A Hinckley 36 Picnic Boat

NARRATIVE: The Hinckley 36-foot boat was just a perfect boat. Though it was 20 years old it seemed brand new and functioned like it. Shane and everyone at Ellis were super gracious and my orientation on the boat which has jet propulsion with a jet stick that I’ve never used before was an hour and a half well spent. By the second day, I was totally comfortable doing anything with the boat. Initially, we just tooled around as everyone had just recovered from Covid and we were tired. Late-day sunset cruises were a must but dawn breaking was fabulous. We spent whole days visiting the outer islands which are not touristy at all. One thing we do every trip is motor over to Little Cranberry Island and have dinner at the Islesboro restaurant. Service, food, and docking are all excellent and we recommend it.

PHOTOS: Some family photos from our day trips with “Lab Adore” and photos from our ocean-side rental (with a private dock) in Southwest Harbor.

Maine Trip July 2022

Poet Louise Bogan wrote Maine is: Where shell and weed wait upon the salt wash of the sea, And the clear nights of stars swing their lights westward to set behind the land.

Our Ellis charter out of Southwest Harbor on Ariel’s Song left us wanting to return again. All furnishings listed were provided, as well as an outdoor grill. The sleeping bags were lightweight so for more warmth will bring our own next time. Big thank you to Darin for his expertise and at ease manner.

Professor Andrew and the Hinckley T40

LOCATIONS : Somes Sound, Northeast Harbor, and Penobscot Bay (Hurricane Island, Castine, and Dark Harbor)

VESSEL:  Hinckley Talaria T40 “Timbuktu”

PHOTOS: Capt. Andrew and Timbuktu in Southwest Harbor

A New Experience in Maine Waters with an Ellis 36

LOCATIONS : Southwest Harbor, Rockland, Duck Harbor

VESSEL: The Ellis 36 “Liberty”

INSIGHTS: Chartering from Ellis Charters was a great experience as well. Any questions that we had on the boat were promptly addressed. It was also nice to have the first-night dockage at the Marina to get familiar with the boat.

An Incredible Experience with the Wilbur 38 Flybridge Cruiser

LOCATIONS : Isle Au Haut, Stonington, Schoodic Penninsula, Winter Harbor, Frenchmans’s Bay, Somes Sound, Northeast Harbor, Suttons Island.

VESSEL: The Wilbur 38 Flybridge Cruiser “Ariel’s Song”

INSIGHTS: If you are not a very experienced boater, I highly recommend getting a captain. The waters around Mt Desert Island have unexpected shallow areas and other things you need to watch out for (like lobster trap buoys). Also, you might want to plan ahead where you want to spend your nights. We hadn’t done that planning, and we ended up spending all 4 nights at the marina in Southwest Harbor. It made it much easier in terms of going out for dinner each night. (Just walk out on the deck and into town or to our car). But if you want to experience sleeping on the boat in other harbors, you should probably plan it out beforehand, or at least have an idea of which harbors you want to visit and do a little calling ahead for mooring availability (call the harbormasters or a local boatyard for each harbor).

Erwin and I on the Ellis 28 “No Altitude”

VESSEL: Ellis 28 “No Altitude”

Family Vacation with a Hinckley T40 in Frenchman Bay

LOCATIONS : Bar Harbor and Frenchman Bay – Private Dock at a rental home

VESSEL: Hinckley Talaria T40 “Timbuktu”

NARRATIVE: Beyond happy with the vessel. She was a joy to drive utilizing the Jet drives. Quiet, stable in all seas, shallow draft, easy to dock/steer and navigate. Very much like a Volvo EPS Pod drive would be. We went all over Frenchman Bay and utilized tender for getting to remote island stops for lunch or moorings. Felt very safe in this boat – an excellent design from Hinckley. Shane at Ellis was awesome to work with and very accommodating for our limited experience. We worked with an excellent captain for 1.5 days and were cleared to operate the boat on our own and now we feel very comfortable after spending a full week with it. We have decided to do this again in 2022. Well worth it and a treasure trove of memories with our family!

LOGISTICS: Be patient with the jet drives–once you learn them though they are a joy to drive.

PHOTOS: A few photos from our time with “Timbuktu” in Frenchman Bay

The Trip of a Lifetime on an Ellis 36 called Liberty

LOCATIONS : From Southwest Harbor, Stonington, North Haven, Camden, Castine Harbor, Bucksport, Hunts Harbor, and Burnt Cove Harbor to Camden with many beautiful harbors

VESSEL: The Ellis 36 Express Cruiser “Liberty”

PHOTO: Curtis Island Lighthouse

Local Cruising near Southwest Harbor

LOCATIONS : We had a wonderful week based on a remote island with trips to Blue Hill, Southwest Harbor, Northeast Harbor, Bass Harbor, Little Cranberry. We also spent one day exploring the Eggemoggin Reach.

VESSEL: An Ellis 36 Express Cruiser

Morning coffee (and some remote work) on our Ellis 36 Express Cruiser

NARRATIVE: We have found a perfect solution for our desire to get out and explore the beauty of Acadia and the Islands of Mid-coast Maine. Ellis is a trustworthy reliable company that has a fantastic fleet and great employees.

LOGISTICS: Follow your charts and be prepared to use radar in the event of fog. 

PHOTOS: A beautiful day on a Maine Island.

A Maine Coast Boating Guide

We would like to recommend “A Cruising Guide to the Maine Coast” for dreaming, scheming, and general Maine Coast vacation planning – it is truly a great resource. This is the kind of book you will want to purchase IN ADVANCE of your soon-to-be Ellis Charter. UPDATE: As of Early 2023 these are OUT OF PRINT. 

IF OUT OF PRINT: Check out the New England Cruising Guide (see below)

Every Ellis Charter Boat includes MAPTECH charts and a copy of MAPTECH’s New England Cruising Guide , which is a very useful guide for finding specific information on each Maine AND New England harbor. If you would like to view a copy of the New England Cruising Guide in advance, you can purchase their ebook version HERE .

A Four-Day Maine Cruise Aboard The Ellis 36 “Hathor”

We, three septuagenarian veterans of sailboat cruising in Maine, were curious what a power-boat charter would be like. So, when we saw a four-day window in Ellis Charter’s schedule, we thought that would be a perfect opportunity to sample the experience. We are accustomed to sailing at speeds between four and six knots while steering clear of lobster pot buoys, so the prospect of cruising at 15 knots without needing to be wary of pot buoys was very appealing. It would allow us to get between destinations expeditiously and enjoy exploring the many shores and hiking trails of outlying Maine islands.

Our cruise aboard “Hathor”, an Ellis 36 Express Cruiser, brought us much sunny weather to enjoy our shore excursions, punctuated with periods of rain, fog, strong winds, and choppy seas as we moved between stops. We welcomed the sense of shelter and robustness that Hathor provides, compared to the exposure to the elements aboard a sailboat. In our 96 hours with the boat, we made stops in the following places, as described further:

• Lunt Harbor, Frenchboro/Long Island (mooring) – pictured below • Burnt Coat Harbor, Swans Island (mooring) • Southern Harbor, North Haven Island (anchor) • Duck Harbor, Isle au Haut (anchor) • Seal Bay, Vinalhaven (anchor) • Merchant Harbor, Merchant and Harbor Islands (anchor) • Islesford, Little Cranberry Island (mooring) • Northeast Harbor, MDI (dock) • Southwest Harbor, MDI (dock)

Looking back at Mount Desert Island from Lunts Harbor – Stop #1

Day 1: After a boat-handling check-out from an Ellis technician that covered docking and picking up moorings, we left Southwest Harbor on Mount Desert Island for Frenchboro, Long Island in the early afternoon. Continue reading →

A few great Maine Boating Destinations

As I sat down with my tax accountant a couple of weeks back (that time of year). I did not necessarily expect a conversation to ensue beyond the invariable discussion of tax codes, liabilities, and write-off potentials. However, as it turns out, my tax accountant is an avid boater with some valuable boating opinions. He discussed many “friendly need-to-see harbors”. Continue reading →

Fox Island Thoroughfare

Thanks for the charter of “Queen of the Cove”, We had a great time and will book again sometime in the future. The boat was comfortable, easy and fun to operate and with the electronics, easy to navigate. Maine is beautiful and the weather the week of our charter was perfect. We particularly liked Fox Island Thoroughfare. That’s the location of the photo with my “Queen” the bow pulpit of “Queen of the Cove”.

Historical Port Tours

LOCATIONS : Primarily exploring old historic marina’s and ports: Castine, Camden, Rockport, Searsport, Belfast, Boothbay Harbor

VESSEL:  The Ellis 36 Express Cruiser  “Liberty”.

The Ellis 36 “Liberty” on Charter in 2019

NARRATIVE: From Camden, you can take ‘day trips’ (to and back) to Rockport and Searsport. Camden’s inner harbor ‘floating docks’ are unique (to me). It is less expensive and easy to take your own tender or you can use the ‘launch service’ back & forth. Make sure you visit the many fantastic Maritime Museums such as Bath’s Maine Maritime Museum and Searsport’s Penobscot Marine Museum (20 min walk from pier). Also, Castine has a great city tour on a golf cart – “Scarlett” [email protected]

A Successful Trip in the Maine Fog

Our week with family visiting was much more memorable with the addition of Ellis’s Too Priceless to enjoy. It comfortably held 10 of us for many day trips to show our South Carolina cousins where the real beauty is – the rocky Maine coast! We are currently in-between boats and this 36’, while a bit larger than we were used to, was a great size and very easy to maneuver.

Our most memorable trip was, well, a memory for many reasons. It was a perfect day and we set off from Western Bay, destination Little Cranberry Island, otherwise known as Islesford. The intention was to visit the museum, artisan shops, the quaint churches on the island and of course, lunch at the Islesford Dock Restaurant where the food is delicious! We did manage to accomplish all that but not before dealing with a typical Maine “suddenly-from-out-of-nowhere” fog bank on the way over. It just came rolling right at us as we came around the bend just before Bass Harbor Head Lighthouse. AND hung with us for the rest of the trip over, clearing out only just as we approached the island dock. While some rental operations might be skimping on bare-bones equipment, this Ellis was fully equipped with sophisticated computers that really did save us that day.

Photo of Bass Harbor Lighthouse courtesy of acadiamagic.com

While waiting for our table for 10, we did all the stops we had wanted to see. After leaving the church which allowed time for reflection, we had a good laugh over what each of us secretly pondered while reflecting in that quiet chapel. Let’s just say all the thoughts tied to “thanks for a safe trip over here” to “please let us have a safe trip back” or “please let the sun burn this fog off while we eat”. Prayers were answered and the trip home was crystal clear so our company could really enjoy the beauty of the islands and Park mountains from the south side of the area.

P.S. The team at Ellis is great as well. I would know. I recently published a customer service satire, critical of the lack of high service standards in many establishments these days. Ellis will never make it into book II unless I change my tactic and pen a book about how it should be done!

A Maine Charter with “Too Priceless”

I would highly recommend Ellis Charters to others and no doubt we will be a repeat customer – everything so so professional.

Here are a few photos from our Trip.

Local Boating Destination Ideas near Acadia National Park

Here are some “destination ideas” as you put together your plans for chartering with Ellis Boat Charters.

LOBSTER BAKE ON MERCHANT’S ROW The perfect Maine day. Merchant’s Row is a collection of islands right off the coast of Mount Desert Island that includes some of the most beautiful islands on the East Coast. Treat your group to a day on the water by setting off from Southwest Harbor or Northeast Harbor in your Ellis Boat charter, motoring by the famous Bass Harbor lighthouse, and casting anchor close to one of the islands.

DINNER OR LUNCH AT ISLESFORD DOCK Dock your Ellis Charter boat at the storied Islesford Dock Restaurant, where you can enjoy classic Maine fare, as well as the works of local artists at the Islesford Artist’s Gallery.

SOMES SOUND Explore what is arguably the only Fjord on the East Coast. It is a body of water running deep into Mount Desert Island and Acadia National Park. Its deepest point is approximately 175 feet (50 m), and it is over 100 feet (30 m) deep in several places. The sound almost splits the island in two. Somes Sound was named for Abraham Somes, who was one of the first settlers on the island. Ask your captain to bring you here to view beautiful ocean-front houses and Acadia’s mountains.

MARSHAL ISLAND Great Island hiking and a wonderful less-known sand beach, with a picturesque cove (Sand Cove) for anchoring. Take the tender ashore for a short picnic on the beach. If you want a bigger adventure, book the boat for two days with a Captain and camp out on the island overnight. Your captain can pick you up the next day to continue your adventure. Details about booking campsites on the island are here: https://mcht.org/preserves/marshall-island

BAR HARBOR TOUR Want to check out Bar Harbor but take the scenic route? Tour along the Eastern part of Mount Desert Island and up to Bar Harbor, where she can dock while you explore Bar Harbor. If you have plenty of time, you could even stop by Schoodic Point or Winter Harbor.

WILDLIFE VIEWING The waters around Mount Desert Island are filled with spectacular wildlife viewing. If you’d like to search for whales, porpoises, or various birds, look no further!

Maine Harbors, Islands, Docks, and Passages…

LOCATIONS : Schoodic Peninsula, Ocean Drive, Eggemoggin Reach, Bucks Harbor, Frenchman’s Bay, Mount Desert Island Area…

VESSEL:  The  Ellis 36 Express Cruiser “Salty Furlough”.

NARRATIVE: I. For the nature lover head northeast to the Schoodic peninsula. Take the inside route passing Mark Island to starboard. Enjoy the scenery along Grindstone Neck and this less frequented region of Acadia National Park. Continue on to Petit Manan for bird watching. If you’re lucky you’ll see the elusive Puffin. II. From SW/NE Harbor head north along the eastern shore of MDI. Enjoy seeing the magnificent turn of the century mansions. Continue north along Ocean Drive and consider how lucky you are to be on an Ellis as you observe the hoards of crowds and vehicles attempting to catch a glimpse of the Maine coast. III. Cruise north and west to cross Eggemoggin Reach of your list of “must-sees” on the Maine coast. Sail into Bucks Harbor for fuel or an overnight assisted by the friendly dock and convenience store staff. IV. Don’t forget Frenchman Bay for excellent deep water cruising and great views of the MDI mountains. While there check out Bald Rock for eagles and seals. Travel north to view the former terminal site for the Mount Desert Ferry where the trains met the steamers for the final leg of the rusticator’s journey to Bar Harbor and points beyond. V. Short trips : a. We visited Islesford and their Dock Restaurant for lunch and dinner. b. We dropped the hook off Eagle Island for a nice lunch spot. c. We stopped into Bar Harbor a couple of times for lunch and dinner. d. We cruised around Baker Island for a different view of the MDI mountains. e. We cruised to the end of Somes Sound for spectacular “inner-island” views.

LOGISTICS: Bar Harbor – Check in with the harbormaster for the possibility to tie up for a few hours. We were able to accomplish this at no charge. Islesford Dock Restaurant – call ahead for reservations. Stock up on snacks and water for the week or longer to minimize provisioning trips.

Share your own Maine Boating Experience:   HERE

Maine Boating Destination: To Rockland and Back

LOCATIONS : Nancy and I started in Southwest Harbor and, over a period of a week, visited Camden, Rockland, Castine, Little Cranberry Island, and Somes Sound. During our passages, we covered the Casco Passage, the Deer Island Passage, the Fox Island Thoroughfare and the Eggomoggin Reach (photo).

VESSEL: Queen of the Cove – A beautiful and very well equipped Ellis 36. The boat was easy to handle, very comfortable in all the sea conditions we experienced. In addition, the boat received several nice comments along the way from others at the docks.

NARRATIVE: We were given a nice reception in Southwest Harbor by Shane and the crew at Ellis Boats. Zach gave us a thorough briefing on the boat including a great tutorial on docking. It turns out the Ellis 36 handles very nicely at docking speeds – I was a bit nervous at first about docking the boat – but was comfortable after two approaches. We choose to use the services of a captain for the first day just to familiarize ourselves with the region. I have wide boat experiences but Nancy does not – and she felt very secure after the first day. The captain sat down with us and helped to work out a great itinerary for the week ahead. The trip started with a passage to Rockland Harbor in windy, bright sun conditions. We decided to stay at harbor docks when possible – and did so in Rockland, Camden, and Castine. The towns are very unique and we got in a lot of walking – exploring each area. The people we met, including the dockmasters, could not have been nicer – we just had a ball. We found the boat to be very comfortable and used either the generator or shore power most nights. The boat was fully equipped with bedding, paper products, galley equipment, etc.. In addition, the boat had a full complement of operational safety gear – very professional. We will do this again next year. Both Nancy and I are happily surprised that Ellis has developed this unique service – we had a great time.

LOGISTICS: Watch the water levels in the boat – fill up at the docks when you have a chance. The shower in the boat is so good you will use it often.

PHOTOS: Queen of the Cove Yacht Interior Photos

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Maine Boating Destination: To Penobscot Bay and Back

LOCATIONS : Penobscot Bay, Bucks Harbor, Belfast, Castine, Northeast Harbor, Somes Sound.

VESSEL: The Ellis 36 Liberty (formerly Eggemoggin Express)

PHOTOS: Here are a few photos from our trip.

Maine Boating Destination: A Journey to Castine

LOCATIONS : Somes Sound, Little Cranberry Island, Northeast Harbor, Eggemoggin Reach, and Castine at 44°23’14.6″N 68°47’43.4″W

VESSEL: The  Ellis 36 Express Cruiser “Too Priceless”.

NARRATIVE: Two summers ago, we chartered an Ellis 36 called “Too Priceless”. We had two full days of cruising in beautiful weather. The first day we had a large crowd of 12-13 and stayed local, going toward Bar Harbor and visiting Little Cranberry Island, Northeast Harbor and exploring Somes Sound and the Western Way. The boat had plenty of room for the large group. The next day three of us made the trip by Bass Harbor up Eggemoggin Reach into Penobscot Bay and docked at Castine for lunch and exploring the town. About a month before our trip, I had read an article about Castine and really wanted to visit. We probably should have taken some extra time and visited Belfast, Stonington, or maybe Camden, but we had plans for an early evening. The boat was a nice ride and easy to handle. We generally cruised at 14-15 knots. We did not overnite on the boat, but I think it would be comfortable for a small group.

PHOTO: From https://castine.me.us

An insider’s sailing guide to yacht charter in Maine & Newport

Sailing in Newport is perfect if you seek stunning sunsets over beautiful yet understated harbours, exhilarating cruising and ultra-friendly locals. And what better way to see it all than on an Oyster Newport Boat Charter? A quintessential American summer destination, Newport is a must-visit spot for New England yacht charters, with a race calendar to entice every level of sailor, from beginners to experienced old hands. The salty air provides the perfect backdrop to explore its eclectic range of monuments, festivals and architecture on a Newport sailboat charter. Meanwhile, sailing in Maine is ideal for explorers, with 3,500 miles of glorious coastline to discover. Historic lighthouses invite you to the horizon, whilst over 6,000 lakes and ponds mean this is one region you will never tire of cruising on a Maine yacht charter.

CRUISING AREA

Sailing in Maine and Newport on a luxury yacht charter

Those sailing in Maine, Newport and the rest of New England in the US summer season can expect warm and humid weather. In July, nearly 15 hours of daylight will mean endless hours spent out on the boat or soaking up the sun ashore, while temperatures rise to around 24°C/71.6°F and wind speeds reach up to 5 mph. And as the summer continues, so does the good weather, making it a reliable destination that as good as guarantees a good tan and lots of lasting memories. One of the world’s favourite sailing destinations, the light winds that blow all year round here will give novice sailors on Newport yacht charters and Maine yacht charters a taste of the freedom and exhilaration a sailing charter provides. New England is most popular in July and August, when the seaside towns and cities come alive with culture and all the best lobster bars are open for business. The area is big enough to escape the crowds on your yacht but the crowds make for vibrant and bustling holiday that will have you dreaming of returning the following year.

Sailing New England on an Oyster Yacht

New England is best experienced by sailing yacht, with countless coves and stunning harbours that motorboats simply can’t reach. An Oyster Newport Boat Charter offers an unmatched on-the-water vacation, in comfort and privacy with a knowledgeable crew who will guide you through the area and cater to your every desire. It is the perfect place to enjoy watersports – snorkelling and diving, water skiing and boarding, as well as surfing. Your perfect US yacht charter awaits.

You can sail on Newport yacht charters and Maine yacht charters on one of our  Oyster sailing yachts for charter , such as the stunning Oyster 625 Black Lion. The Oyster 625 offers spacious interiors for a sailing yacht, with a generously proportioned galley, a full-beam owner’s suite, two en-suite cabins forward and a fourth guest cabin a guest cabin. Designed for outdoor living, with safe navigation and easy sailing facilitated by a large cockpit, flat aft deck and forward sundeck, it is made for yacht charters.

CRUISING DESTINATIONS

Sailing in Newport 

A Newport sailboat charter offers the chance to discover historic sites hailing back to Newport’s Colonial history, alongside musical and arts festivals that light up the city and incredible beaches for sunbathing and watersports and impressive architecture. All this makes Newport the destination that keeps on giving. Start by taking a walking tour of Newport’s Old Quarter and view the magnificent mansions in the Bellevue Avenue Historic District – it’s not hard to imagine how life was here in the past. If you’re a surfer, you will want to catch some waves at Easton's Beach before enjoying a relaxed BBQ on its golden sands. If you are an art lover, you are in for a treat – Newport is home to over 30 private art galleries offering everything from contemporary artworks to the more traditional. Whatever your taste, there is something for everyone. No Newport Boat Charter holiday would be complete without a visit to the famous Martha’s Vineyard. This picture perfect island is home to around 16,000 people but the population swells to more than 100,000 people during the summer months. Drink in the brightly-painted seaside cottages and cobblestone streets, and marvel at the pristine beaches at Chappaquiddick Point. After lunch at an elegant dockside bistro, head back to the yacht for some adrenaline-fuelled watersports.

Craving an island escape? Cruise over to Nantucket on your Newport sailboat charter, where the rich and famous go to while away the long hot summer months. Drop anchor and spend the day drinking in its one-of-a-kind history and make sure to stop by the whaling museum where you will discover how hard life used to be in this relaxing and entertaining destination. Designated as a National Historic Landmark District, it is the finest surviving architectural and environmental example of a late 18th- and early 19th-century New England seaport town. When you’ve enjoyed your fill of history, why not take a good book and enjoy some downtime on one of the delightfully uncrowded stretches of sandy beach? And when you’ve recharged your batteries, you’ll be ready for the evening. The island really comes to life at night, with vibrant harbourside nightlife which is perfect for an evening of bar-hopping and enjoying locally-caught seafood. All this gives just a taste of all there is to explore for those onboard New England yacht charters.

On land or on water, the best time to take a Newport Boat Charter is during the months of July and August, when the city bustles with activity and the weather is reliably and gloriously sunny. Don’t miss the Newport Folk Festival in July and Jazz Festival in August, both of which were established in the 1950s and have been a draw to the city ever since. (The Newport Folk Festival is infamous as the event where Bob Dylan famously ‘went electric’, much to the fury of the audience of traditionalist folkies.)

Sailing in Maine

Maine  is renowned for its dramatic lighthouses, rugged mountains and enchanting sea life, found just 20 miles from the coast. With a coastline just shy of 3,500 miles, there is a lot to discover. But the joy of the area is that once you are there, you don’t need to waste time on long passages between ports – it is possible to enjoy Maine in bite-sized chunks and cruise at your leisure. The whale-watching season runs from mid-April to September and captivates thousands on crewed sailing yacht charters with the prospect of sighting humpback whales, pilot whales, minke whales and finback whales, as well as rarer visitors like sei whales, sperm whales, orcas and right whales. When you’ve had your fill of wildlife spotting, sail in Maine’s MidCoast and islands. This is a veritable paradise, with its many secluded coves, inviting harbour villages with a view and some of the best lobster you’ll ever taste especially in Swan's Island. Maine is renowned for its seafood restaurants, ranging from the local lobster shacks to five star restaurants. You can discover plenty of great places to eat and drink at in our  Maine Insider Sailing Guide. 

Sailing in Maine in July and August guarantees the best weather as temperatures reach up to 25°C/77°F and wildflowers and blueberries shoot out from the bushes, adorning the landscape. These months are typically warm and mild - the perfect climate for outdoor activities and watersports. (Don’t be put off by Maine’s famous fog – it is a truly atmospheric experience that is as much part of any trip as sun-filled days.) You can hike, camp, swim, water ski, cycle, white water raft and kayak the summer away on board a luxury New England yacht charter with Oyster.

GET IN CONTACT

Learn more about how to charter a sailing yacht in New England with Oyster by taking a look at our Maine sailing guide  here . Discover  Oyster luxury sailing yachts for charter  or contact Oyster Charter Manager, Fiona McCarthy to begin planning your trip.

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Your Guide to the BEST Maine Sailing Tours | Windjammers, Sailboats, & Schooner Tours

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Everyone knows that Maine has a stunning coastline and breathtaking views of the Atlantic Ocean from pristine beaches to rugged cliff walks. But, have you ever considered seeing Maine from the water? Set sail on an exciting adventure on one of the best Maine sailing tours onboard a windjammer, sailboat, or schooner.

We think it’s the best way to view the Maine coast , and what could be more exhilarating than setting sail out of a Maine harbor aboard a tall-masted schooner? Down the coastline from the Downeast & Acadia region to the Southern Maine Coast , there are so many sailing excursions to choose from.

The best part? You can sit back and relax while someone else does the sailing and navigating. Or, you may lend a hand and hoist a sail if you prefer. There’s no better way to experience the beauty of Maine than on a historic sailing trip, so check out these options for your next visit to Maine.

Downeast & Acadia Sailing Tours

Downeast windjammer cruise lines.

If you’re looking for a variety of options for sailing, Downeast Windjammer Cruise Lines in Bar Harbor has you covered. Offering a Sunset Sail, a Morning Sail, and an Afternoon Sail, there’s a wonderful experience no matter the time of day. Each sail has its own vibe.

The Sunset Sail is the most popular cruise that Downeast offers. It includes live folk music, beer, and wine for sale. Or, enjoy sailing in Frenchman Bay during the Morning Sail, which is more relaxed but still offers breathtaking views of Acadia National Park .

The Afternoon Sail is perfect for those looking for a narration during the sail. The captain will point out points of interest, regale you with the local history, and discuss wildlife.

No matter the sail, you can bring a picnic of snacks along, and most sails are pet-friendly.

Downeast Sailing Adventures

Southwest Harbor

Step aboard the Real Maine for an unforgettable experience sailing around the Cranberry Islands, Acadia, and Somes Sound. This tour will take you by lighthouses, past gorgeous homes on the shore, and by working fishing boats.

Book a private charter or a group day sailing adventure for up to six passengers. Downeast Sailing Adventures has daily sails on its 33-foot boat Surprise and its 38-foot boat Swan .

Sail Acadia

Northeast Harbor & Southwest Harbor

Sail Acadia offers trips out of two harbors, Northeast Harbor and Southwest Harbor . Sailing trips can be either shared or privately chartered. Private charters can be catered to your preferences with sailing instructions or a stop at an island for a picnic included.

Book a morning sail for calm waters with gentle sea breezes and good opportunities to view local wildlife. The morning sail is suggested for first-timers and children.

Or, book an afternoon sail for stronger winds that will make the sailboat cruise faster. This sail typically sees seals along the route, and the captain will often give a narration of the wildlife and history of the area.

Another option is a sunset sail for a romantic experience. This sail will have you seeing gorgeous sunset views on calm waters.

Schooner Tours in MidCoast Maine

Schooner stephen taber.

If you’re looking for an all-inclusive overnight experience, book a sail aboard the 150-year-old Stephen Taber . Each sail includes accommodations in one of 12 cabins, meals, wine (on evening sails), a lobster bake and barbecue on the beach, and evening entertainment.

Guests can choose from a themed trip or a private charter from Rockland Maine . Themed trips are a lot of fun and span from three to six nights, depending on your preference.

Enjoy trips such as Culinary Explorations; ‘Wine, Dine, and Chocolate;’ Yacht Racing Regatta; Penobscot Bay’s Hidden Gems; and more. These trips are sure to be memorable experiences, and by the end of the trips, you’ll feel like family with the other guests on board.

Here are more MidCoast Maine boat tours that are part of the Maine Windjammer Association like the Schooner Stephen Taber : Schooner American Eagle | Captain Tyler King | Rockland, ME Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME Schooner Ladona | Captain J.R. Braugh  | Rockland, ME Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

A Morning in Maine

If you’re strapped for time and want a shorter sail, A Morning in Maine’s sailing trips are a wonderful experience. The two-hour sailing adventures take place aboard a 55-foot ketch that passes lighthouses and other schooners.

The morning trip is perfect for those looking for calm sailing. The mid-afternoon sail has windier conditions for a faster sail. Evening and sunset sails feature beautiful sunset views and a relaxing ride. Guests are often given the chance to try to steer the boat as well.

Schooner Surprise

The Schooner Surprise has been sailing for over 105 years, with 30 of those years setting sail out of Camden Maine . Guests can book a two-hour sail with views of the lighthouse, summer houses and views of Penobscot Bay .

These family-friendly sails let guests, including children, take the wheel while out at sea. Special sails include a Full Moon Sail that features live music during sunset and a trip lasting two hours into the night. Or, book a fireworks view sail or a Birding and Marine Life Tour with an ornithologist.

Portland & Casco Bay Sailing Tours

Portland schooner co..

Portland Schooner Co. sets sail from Portland Maine and cruises through Casco Bay for a delightful trip along the coastline and past lighthouses and ocean life, like seals. On the two-hour sail, bring your own picnic and even alcoholic beverages for a relaxing, scenic time on the water.

These sails are perfect for all ages. Sails take place throughout the day on one of the five historic wooden schooners. The sails are relaxing and do not include narration, but the crew is available to answer any questions that guests may have.

Maine Sailing Adventures

Maine Sailing Adventures offers traditional two-hour and themed sails through Casco Bay . What sets it apart from other sailing companies is its unique themed sails. Try an acoustic sail that features live music. Or, try a wine sail that includes a wine tasting for adults.

Have you ever heard of a yoga sail? This ship can accommodate up to 12 guests for a yoga class that you won’t experience anywhere else. Enjoy amazing views of the water while working on your poses.

Sail Portland Maine

If you’re looking for an intimate sailing adventure, Sail Portland Maine has you covered. Guests can choose a private charter or a public trip. The public trips’ capacity is 12 people, so you know that your sail won’t be too crowded.

Day and sunset trips are two hours in length and pass by all of the famous Casco Bay features — like historic forts, lighthouses, and if you’re lucky to spot them, seals. Guests are welcome to bring their own food and drinks, while bottled water is complimentary on board.

Schooner Tours on the Southern Maine Coast

The pineapple ketch.

Kennebunkport

There’s no better way to see the Kennebunk River than sailing on it. The Pineapple Ketch departs from Nonantum Resort for a dazzling trip along the river and the Kennebunkport coastline.

You’ll see gorgeous seasonal cottages, including the famous cottage of President George H.W. Bush. Enjoy views of the Goat Island Lighthouse, local harbors, seabirds, and seals.

Each sail includes complimentary bottled water and sodas, but guests are also welcome to bring their own food and beverages.

Silverlining Sailing

Silverlining Sailing offers one of the most intimate sails in Ogunquit Maine . Each boat has the capacity for up to six passengers, making for a small group sail. Sails typically last two hours, departing from the quaint Perkins Cove village.

There are five trips daily (weather permitting) from early morning through to a sunset sail in the evening. Enjoy stunning ocean views, gorgeous waterfront homes, views of local beaches, and harbors.

Since this is a smaller group sail, guests get the opportunity to try their hand at taking the wheel and steering the schooner.

Broad Reach Adventures

Broad Reach Adventures has two-hour sails, half-day and full-day sails, and chartered sails from Saco Maine , so there’s a sail to accommodate your busy schedule.

Each one allows guests to see beautiful views of the Saco River, Saco Bay, Biddeford Pool, Old Orchard Beach , and lighthouses along the way. Longer sails provide guests with the opportunity to disembark and explore uninhabited islands.

A unique feature that Broad Reach Adventures offers is the opportunity to add a massage or professional photographer. These experiences are available on certain dates and times, so book ahead if you’re interested in these add-ons.

Sailing Lessons & Boat Rentals

If you want to learn to sail, sailing instruction is often available as part of your charter package.  Private charters  of sailboats on the Maine coast allow experienced sailors to explore the coastline on their own.

Private sailors will find  hotel marinas  for lodging in Maine’s best harbors. If you time your sailing cruise right, you might witness seals, porpoises, whales, or other tall ships.

Watching the sunrise from the deck of a schooner is one of life’s simplest, most satisfying pleasures. Of course, the spectacular Maine scenery is always included on your sail.

Set Sail on Sailboat & Schooner Tours From Maine This Season

Now that you know about all of the sailing trip options, it’s time to set sail into the open waters of Maine. From two-hour trips of the bays and harbors to overnight excursions, there’s an experience awaiting you on your next getaway.

Each Maine sailing company offers its own unique trips aboard safe, well-maintained schooners. Relax, unwind, and feel the ocean breeze in your hair as you cruise through the lapping waves of Maine’s Atlantic shoreline.

The VisitMaine.Net team is the small team of authors and editors that research and write our in-depth guides throughout the site and update past articles to make sure they're still super valuable to you. We have one goal: to help you fall more in love with the state of Maine!

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Travel+Discover Maine – The unofficial guide to exploring the great state of Maine. Not affiliated with any official tourism entities.

Copyright Travel+Discover Maine 2024 Images Courtesy Greg and Heather Burke unless otherwise noted.

SAIL ACADIA

Sailing charters & lobster tours at acadia national park.

• Most Popular Tour

Mount Desert Island Sailing Tour

Sail Acadia National Park aboard a traditional Friendship Sloop – Maine’s original lobster boat! Built in Friendship, Maine in the late 1800’s, these handsome traditional sailboats were used by coastal fishermen to haul lobster traps by hand under sail. Take part in Maine’s maritime heritage and enjoy sailing smooth waters, abundant wildlife and spectacular coastline of Acadia National Park.

• Hour Glass 2 - 3 Hours
• User All Ages
• Info Up to 6 passengers
• Great for Families!

Lobster & Nature Tour

Enjoy a nature cruise aboard the Elizabeth T, a real Maine lobster boat! Haul lobster traps, visit Somes Sound, and see a seal colony on a perfect size boat for sightseeing, island picnics, and lobster fishing demonstrations.

• Hour Glass 2 Hours
• Info Shared Tours are up to 16 passengers; Private Charters are up to 21 passengers

Sail Acadia National Park

Escape the crowds of Bar Harbor and explore the spectacular coastline of Acadia National Park.

Sail aboard a classic Friendship sloop or a real Maine lobster boat for a private or shared tour of Maine’s most beautiful coastline along Mount Desert Island.

Sailing and lobster boat cruises depart several times each day from Southwest Harbor and Northeast Harbor, just 15 – 20 minutes from Bar Harbor.

At Sail Acadia we maintain and operate our locally built wooden boats with a great respect for Maine’s maritime heritage. We believe in smaller groups and personalized attention for an authentic boating experience in Acadia. Our captains and crew will share their local knowledge and give you their best tour of Mount Desert Island.

Five-Star Sailing & Boat Tours ★★★★★

We were blown away by the service at Sail Acadia. We did a mid-morning private tour for 7 of us. We were able to bring our own mimosas :) Our captain and first mate were knowledgeable, inviting, friendly and easy going. They were very welcoming to our pup! They had blankets and cups on board. Definitely recommend!

We thoroughly enjoyed our sunset cruise with Mike and Kelly. Mike told some great stories of the area, we took wine and dinner to have on the boat, and we enjoyed seeing guillemots and porpoises in the bay. The wind was very light that evening so we had to motor a bit, but it was such a treat to be out on the water on a 120 year old wooden sail boat. We loved it!

We booked a 3 hour sunset sail and it was so much fun. It wasn't the windiest day, but being on the water on a beautiful summer night watching the sun go down can't be beat. We saw plenty of porpoises and other sea wildlife throughout the ride. Bonus points: the tour is BYOB so we brought a bottle of wine with us and the crew provided cheese, crackers and snacks. Thanks for having us!

An awesome experience we can't recommend more highly. Not only was it a fantastic sailing experience, the crew were informative about the area, history, wildlife and the things we were seeing along the way. The crew was great, the boat charming and historic. The best afternoon we have had in Maine for as long as we can remember!