sailboat long island

SAG HARBOR SAILING

Rentals, lessons, charters and summer youth programs, explore sailing lessons, rentals and youth programs, sail the hamptons, home to some of the world's most beautiful waterways, sailing boat rentals.

Our 23-foot Pearson Ensign sailboats can comfortably accommodate up to six people. Whether you choose to sail with a captain or on your own, you can fully enjoy your time on the water.

Additionally, our Commodores Club offers seasonal savings for those who sail more than three times.

LEARN TO SAIL

Our instructors offer private lessons on our company’s fleet of 23-foot Pearson Ensign sailboats. Each private lesson can accommodate up to four students, ensuring personalized attention and effective learning.

Get certified with our 2-day American Sailing Association beginner sailing certification program.

SUMMER YOUTH PROGRAM

Our week-long program features a wide range of activities on the water including sailing, wake boarding, tubing, water skiing, learning to captain a boat, fishing, paddle boarding, SEABOBS, swimming and more.

Sessions are held Monday–Friday, 9–12:00pm for ages 9–16 and operate from July 1 to August 30. Sign up for multiple weeks or just for the day.

TWENTY YEARS OF SAILING IN THE HAMPTONS

"We had a great day out on the water! The boat was in awesome shape and the staff were super helpful!"

"We rented a sailboat on Sat. Beautiful day. Captain Mark was great and let us be hands-on as possible sailing the 23 ' Pearson Ensign. Would recommend highly!"

"My wife, 2 boys and I hired Mark for the sunset cruise. He was great, the weather was beautiful and our evening was perfect. I highly recommend."

"Great trip fishing with captain Bob! He was great with kids. Two hour fishing trip is just right."

Long Island Boat Rentals

Located in Port Washington, Long Island offers Captained and Bareboat Rentals, Yacht Charters, Semi-Private Training Classes, Water Sports Adventures and On-the-Water Fun!

Are You Ready for an Adventure?

• Elixir Yacht Charters – luxury party yacht for up to 24 guests
• Memories on the Boat  – With Friends, Family, that Special Person, Coworkers and Clients!
• Water Sports – Tubing, Waterskiing, Wakeboarding and Swimming.
• Sunset Cruises – Romantic, Booze, Dock & Dine and Catered Cruises
• Sightseeing – Statue of Liberty, Manhattan, Gatsby Homes, Lighthouse, Historical and Local Destinations
• Fishing – For Fluke, Striped Bass, Bluefish, Blackfish and Porgies.
• Celebrate –   Birthdays, Reunions, Bachelor/Bachelorette and Engagements
• Captained Cruises
• Have a Flarty!
• Pick Your Adventure
• Rent a Boat
• Charter a Yacht
• Get Training

What’s Happening on the Water

Special events.

STAY TUNED FOR TICKED ELIXIR TRIPS IN JULY AND AUGUST 2023!

LIBR UPDATES

New carefree boat club location in huntington specials going on now for 2023, new yacht charters available see page for details, captain rentals & charters, captained rentals and elixir yacht charters are bookable online.

If your preferred date is unavailable, use the waitlist to secure your spot in line for Captained Rentals & Yacht Charters (6 passengers), and charter dates for “ ELIXIR ” our 24 guest luxury party yacht.  Select your vessel, date and check off “Captain Requested” to request captained services.

If you tried to book a bareboat rental that is currently booked, you can use the waitlist to be the first in line for a cancellation on your preferred date or boat.

Visit our info page for the waitlist and rate sheets.

Full Day Rentals Available – get the time in between half day rentals as a bonus and enjoy more time on the water!

Six (6) passenger maximum on all captained rentals, no exceptions.

Semi-Private Powerboat Training Classes offered Tuesday & Thursday mornings.

Purchase Gift Cards

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Special Packages and Promotions

“ELIXIR” has launched! –  Our new custom designed party yacht for 24 guests

5-Pack – 15% off all your rentals if you rent 5 times. So easy, just pay as you go. Even without the 5-pack, on your 5th rental, we will give you the 15% discount. 

Military Discounts – 10% off for all active, retired, or reserve military veterans with a Valid Military ID.  $100 maximum per rental, not to be combined with other discounts/offers, may not be used to purchase gift cards or used on previous reservations.

First Responders 15% off – Monday-Thursday –  All active Police officers, Firefighters and EMTs receive 15% off our weekday rates on any of our boat rentals. Not to be combined with other offers or promotions.

Testimonials

This is my second great experience on a Long Island boat rental and it was wonderful. Gorgeous weather, courteous crew and lovely views. My husband and I can’t wait to come back again soon!

My brother-in-law was in town and we wanted to do something fun with him. He’d never been to LI, and we thought the best way to see it would be a cruise on the water. We rented a boat here after being referred by a friend, and we had a blast out there! It was just as exciting for us to get a different perspective on the island as it was for him. We don’t fish, but these boats would be perfect for that I imagine.

I reserved a 22.5 foot Scout online for 3 hours. We arrived and the boat was ready for us. Super clean and new motor looking. We were very happy with the young man who helped us and gave us guidelines of the waters there in Northport. Even though my husband is a seasoned boater. GPS system was perfect too. Very happy!

I have rented three times so far.  The boats are always in excellent condition, and the staff could not be more friendly or more helpful.  Get out on the water!

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Long Island Sailing

Sailing has been a Long Island pastime for centuries, and the popularity of the sport won’t be slowing down anytime soon. Surround by the Long Island Sound and the Great South Bay, it is no wonder why this water sport is a favorite of both locals and visitors alike – not only is it fun to sail, but enjoying the beauty of sailboats is an experience that spectators on the shores of Long Island simply can’t pass up. Whether you’re new to sailing, and simply looking to get some lessons as you gain your sea legs, or you’re an old ... Read More Sailing has been a Long Island pastime for centuries, and the popularity of the sport won’t be slowing down anytime soon. Surround by the Long Island Sound and the Great South Bay, it is no wonder why this water sport is a favorite of both locals and visitors alike – not only is it fun to sail, but enjoying the beauty of sailboats is an experience that spectators on the shores of Long Island simply can’t pass up. Whether you’re new to sailing, and simply looking to get some lessons as you gain your sea legs, or you’re an old pro looking to upgrade your boat, there are local marinas and sail boat specialists here on Long Island that can get you out on the water in no time. Show Less

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Oakcliff Sailing Center

4 South Street in Oyster Bay 516-802-0368

Sag Harbor Sailing

51 Pineneck Ave in Sag Harbor (631) 725-5100

Sail Long Island

Brewer Yacht Yard in Greenport 917-912-6342

SailTime Long Island

90 Colonial Drive No. 2 in East Patchogue (877) 724-5846

The WaterFront Center

1 West End Avenue in Oyster Bay (516) 922-SAIL

Want to be added to the Sailing Page? Call 631-406-4410 or Email Us for details!

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Captain Steve's Sailing Charter

Captain Steve offers private sailing charters aboard Sales Call,  a 34 Foot Beneteau Oceanis for up to 6 guests. Customizable to whatever type of sailing adventure you are interested in, we are here to help. Sit back, relax and soak up the sun, we got you covered! Take the helm, unfurl the sails, the boat is yours to command. Drop the anchor, go for a swim, uncork the wine, no problem. Whatever the request, just ask!

Available for Any Special Event

Romantic Getaway

Watch the Sunset

Family Time

Proposals, Engagements and Weddings

Private and Group Sailing Lessons

See Historic Lighthouses

Perfect location for Social Media & Photo Shoots

Dock and Dine

Anchor, Swim and Chill

Why Choose Us

Highly experienced and U.S. Coast Guard Certified 

Top notch vessel and equipment

"Beyond the ordinary" customer service

Location, Location, Location

Create memorable experiences

Our Gallery

What to Expect on Board

Captain Steve sails out of Manhasset Bay in Port Washington. Come see the mansions of the Gold Coast of Long Island, sail under the Whitestone and Throgs Neck Bridges. Cruise to City Island for a Dock N Dine experience like no other. Drop the anchor by Half Moon Beach in Sands Point, go for a swim, chill, watch the sunset.

Do you have any questions?

Our most popular excursions.

Sailing Lessons

             Private Sailing Lesson

If you want to learn how to sail or brush up on your skills. I offer hands on sailing instruction and practice for beginners and experienced sailors.

$150 per hour Monday - Friday

2 hour minimum per session  

Limited to 3 participants per session

Sunset Sail

3 hour private charter weedays

Set sail on the coast of the Long Island Sound to see the magnificent sunset over the NYC skyline. Perfect for families, proposals, anniversaries, birthdays and celebrations!

Sunset Sail. 6 Guests Maximum

3 hrs for $650  Weekdays

1/2 Day Sail

              4 Hour private charter 

Enough time to sail under the Throgs Neck and Whitestone Bridges or head East to the Execution Rocks Lighthouse, see the Mansions of the Gold Coast, drop the anchor. 6 Guests Maximum

4 hrs for $775  Weekdays

Our Reviews

My family and I had a great day on the water with Captain Steve, who made the experience fun, as we cruised the Long Island sound, with a solid 10-15 knots worth of wind. The highlight was when my daughter took the 'wheel' and steered the boat, and felt the wind in the sails...she's hooked.

• What are your rates? All Charters are customizable to suit your needs. Tell Captain Steve exactly what you are interested in and he will curate a charter to meet your needs and exceed your expectations. Rates - 2 hour minimum, includes up to 6 passengers and USCG certified Captain $200 per hour Weekdays $250 per hour Weekends $300 per hour Holidays Sailing Lessons Monday - Friday 8 am- 4 PM only - 3 participants maximum - $150 per hour - 3 hour minimum
• What to expect onboard? Please arrive 15 minutes prior to your scheduled start time. Please also allow time to park, as there is no parking for Marina guest on the Hotel property. Once aboard, you will be briefed on safety procedures and discuss our sail plan. Sailing is an active sport, winds and sea state can change at anytime. A sailboat when under sail will heel (tipping to one side or the other caused by the force of the wind on the sails) That being said, it's nothing to worry about, the heeling effect can be controlled by the Captain and this sailboat will not tip over. You will also have the option to motor around (without unfurling the sails) or drop anchor for a more stable experience, giving you the opportunity to swim, dine, sun and chill on deck. The 2007, 34 foot Beneteau Oceanis 343 Sailing Yacht is equipped with a roller furling main and head sail for quick and easy departure and return. A large cockpit area that will comfortably seat 6 passengers. If interested, you will have the opportunity to take the helm, trim the sail and pilot the boat. There is a Bluetooth Stereo, TV, Head (bathroom), full kitchen ( refrigerator, microwave, stove and oven). There is swim ladder and platform with outdoor shower. There is also a collapsible Bimini top for shade. Please bring food, beverages, sun screen, hats, towels, sun glasses. Life jackets for children under 13. I have several available, if needed. Sorry, no Extra-Large hard sided coolers are allowed on board. All personal items must be secured for sailing in windy conditions. Barefoot on the boat is preferred, if not, please wear soft soled shoes. No shoes with heels are permitted on board. If winds are forecast to exceed 20 knots or thunderstorms are in the area, the Captain reserves the right to delay or postpone the sail for another date. Safety is top priority!
• What are the features of your boat? Bluetooth Stereo Bimini top for shade - collapsible for full sun Full Kitchen - microwave, oven, stove, refrigerator Head (Bathroom) with Shower Transom (back of boat) Swim platform with Shower Interior cabin with table Television Swim noodles Life jackets are available for everyone on board. You are welcome to bring food and beverages, including alcohol. Just a quick reminder to drink responsibly, the Captain has the right to terminate a charter due to intoxication. Note it is cooler out on the water, so bring extra clothes, especially for an evening cruise. Bathing suit and towel if you plan to swim. **Please note, no large hard sided coolers with wheels are allowed on the boat. You are welcome to bring to to them to the dock and items will be transferred to the refrigerator and smaller cooler on board.
• Whats your cancellation policy? We offer a full refund up to 7 days prior. 50% refund up to 3 days prior. Reschedule due to bad weather, it's the Captains Call. Saftey is our #1 priority!
• How many guests can I bring? U.S. Coast Guard requlations require that the # of guests be limited to 6 people regardless of age. Sorry no dogs or pets are allowed on board.
• Are Children allowed? Yes, but note this is not recommended for children under the age of 3. All children under 13 are required to wear a life jacket at all times when on deck. I have a several life jackets available, but for best fit, bring your own if available.
• Do you offer gift certificates? Yes, you can buy a Gift Card for any amount and apply it towards any sailing experience. Please find the link to Gift Cards below and in the main menu. https://www.captainstevesailing.com/gift-card
• Where do I get on board? Call or text Captain Steve for detailed directions 516-902-9099
• Where can I park my car? Please note that there is no parking available on the Hotel property for Marina guests. Metered parking is available on Main Street & the 'Passport Parking' app can be used to refill your meter remotely. Parking is also available across the street from the Hotel in the residential neighborhood or at the Port Washington Town Dock parking lot at 347 Main Street in Port Washington.
• What is the deal with inclement weather? We reschedule due to inclement weather. If the winds and seas are too rough for sailing we reschedule. If it's raining or lightning storms are tracking toward our area we reschedule. Sustained winds over 20 knots will warrant rescheduling. Note, many weather forecasts are for the Tri-State area, we generally sail within a 10 mile radius, and keep a close eye on the local weather.
• Is there a bathroom on board? Yes, there is a fully functioning bathroom on board. Toilet paper is located in the cabinet under the sink. To flush the toilet, you can move the lever to the left ( wet side) this will allow water to enter the toilet bowl when pumping up and down. To empty the toilet bowl, move the lever to the right and pump up and down until rempty. Please do not put anything inside the bowl aside from human waste or toilet paper. Paper towels of any kind will clog the plumbing system. There is a waste water holding tank that holds the waste and is pumped out once each week. There is no access to a public bathroom at the Fathoms Hotel for marina guests.
• What is a Community Sail? A Community Sail is a semi private sail where each seat is sold individually. There is a maximum of 6 guests. You can purchase 1-6 seats for a Community Sail based on availability for that date.
• Do you offer sailing lessons? Yes, I offer hands on sailing lessons. Monday to Friday only 8 am - 4 PM Private lessons only, limited to 3 participants per session. $150 per hour, 2 hour minimum per session

Get in Touch

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[email protected]

516.628.7156

PRIVATE SAILING CHARTERS, SUNSET CRUISES & SAILING LESSONS IN OYSTER BAY, NY

Experience the beauty of long island's historic gold coast.

 Situated in the heart of Long Island's Gold Coast, just 30 miles from Manhattan, Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. 

In 2024, Oyster Bay Harbor was designated as ‘Best Harbor’ winner for the Mid-Atlantic region by the US Harbors organization! 

Home to former U.S. President Teddy Roosevelt, Oyster Bay is the only source of traditionally farmed oysters from Long Island providing up to 90% of all the oysters harvested in New York State!

SAIL IN COMFORT

You'll sail aboard  WINDSWEPT , a meticulously kept Jeanneau Sun Odyssey 36i featuring a spacious shaded cockpit and a secured deck. WINDSWEPT is professionally maintained and equipped with modern electronics and USCG approved safety gear. Whether you are celebrating a special occasion , interested in learning to sail, or planning a client outing, your time aboard WINDSWEPT will be both memorable and enjoyable!

S/V  W I N D S W E P T

2012 Jeanneau 36i

2-Hour Sailing Charter

Private sailing charter for up to 6 guests

3-Hour Sailing Charter

Half Day Sailing Charter

Full Day Sailing Charter

Popular charter experiences.

SUNSET CHARTERS

Sail into the sunset and enjoy one of the best shows on earth! View our photo gallery for some of our favorite Oyster Bay sunset photos!

SIGHTSEEING HARBOR TOURS

Learn about historic Oyster Bay Harbor while taking in the diverse wildlife and spectacular views of the sandy bluffs and mansions that line the bay!

SAIL & SWIM CHARTERS

Cool off and go for a refreshing swim before or after your sail! Water temperatures in Oyster Bay Harbor can reach nearly 80 degrees in August! WINDSWEPT is equipped with floats for everyone to enjoy!

SAILING LESSONS

Learn the basics of sailing a modern monohull. Private lessons cover everything from sail handling techniques, to sailing terminology, and the various points of sail!

PHOTOSHOOTS

Have professional photos taken with Oyster Bay and WINDSWEPT as your backdrop! Book time an hour before sunset for the best natural lighting!

TEAM BUILDING EXERCISES

Teamwork and effective communication are required to sail a boat well! Develop new skills while working together! Contact us to discuss your objectives and we'll create a great experience for your team! 

CLIENT OUTINGS

Take your client relationships to the next level with a memorable sailing experience aboard WINDSWEPT! Weekday sunset cruises are ideal for entertaining clients!

DOCK & DINE CHARTERS

Book a full day charter and sail to a nearby harbor! Head into town to try a new restaurant, indulge in a cocktail or check out an antique store! Finish the day with a relaxing sail back to Oyster Bay Harbor. 

GETTING TO THE BOAT

WINDSWEPT is moored in Oyster Bay Harbor, on the North Shore of Long Island. Upon booking, directions to the boat will provided in your confirmation e-mail. For those traveling from New York City, the marina is steps away from the Oyster Bay LIRR station or a 20-minute Uber ride from the Hicksville LIRR station. 

Oyster Bay has quite a few local attractions , restaurants, and bars that  you may want to consider before or after your charter, many of which are in walking distance of the marina! 

CAPTAIN JONATHAN

Owner/operator, uscg licensed oupv captain.

Jonathan is a lifelong sailor and U.S. Coast Guard licensed charter boat captain with decades of cruising, offshore and racing experience.  A Long Island native, Jonathan was taught to sail at an early age by his parents, who were avid sailors. Growing up, his summers were spent on the water sailing harbor to harbor on Long Island Sound.

FREQUENTLY ASKED QUESTIONS

What is the maximum number of people allowed per charter.

Your party can include up to 6 guests. Children are included in this limit, which is set by the U.S. Coast Guard for this type of charter and strictly enforced.

WHAT SHOULD WE BRING ON THE BOAT?

Your charter includes bottled water and a variety of soft drinks. You are welcome to bring your own food and beverages, including alcohol. We also encourage you to bring sunscreen. Shoes with non-marking soles are permitted (no shoes are preferred). Pack a bathing suit and towel if you'd like to go for a swim!

CAN WE CUSTOMIZE OUR EXPERIENCE?

Absolutely - in fact we would encourage you to! Call us to discuss the experience you envision and we will do our absolute best to accommodate! 

WHAT ARE THE SAILING CREDENTIALS OF YOUR CAPTAINS?

All of our Captains are licensed by the U.S. Coast Guard to operate sailing vessels up to 100 gross tons and have years of sailing experience.

I TEND TO GET SEASICK - SHOULD I BE WORRIED?

Oyster Bay is protected and typically very calm, even on windy days! That said, seasickness medication is carried onboard and can be taken proactively if you are concerned about getting seasick.

WHAT HAPPENS IF THERE IS BAD WEATHER?

Summer weather on Long Island can be uncooperative at times. While we cannot guarantee perfect weather for every charter, you are able to reschedule your charter at no cost if the forecast is calling for >40% of rain during the hours of your charter, heavy winds or lightning. In the event that we cannot find a date that works for your group, we will gladly issue a full refund.

WHAT IS YOUR CANCELLATION POLICY?

You may cancel or reschedule your charter at no cost up to 10 days prior to the scheduled date. If you cancel within 10 days and are unable to reschedule, you will receive a full refund minus your initial deposit.

CAN WE BRING A COOLER?

Absolutely, as long as it is a soft cooler!  Hard coolers can damage the deck when they are moved. WINDSWEPT is equipped with a YETI soft cooler that you are welcome to use. The boat also has onboard  refrigeration.

TESTIMONIALS

“Me and my husband booked a 3-hour sunset charter and were blown away by the natural beauty of Oyster Bay Harbor. Captain Jonathan was attentive and welcoming and the boat was beautiful! This experience was the highlight of our vacation and we would not hesitate to book again! 

- G. Moreira

Thanks for your inquiry! We will respond shortly!

2024 SAILING SEASON & HOURS

All hours subject to weather, april 27th - may 31st monday - friday: 5:30 pm -  9 pm saturday - sunday: 9 am - 9 pm june - august  monday - friday: 5:30 pm - 12 am  saturday - sunday: 9 am - 12 am september tuesday - friday: 5:30 pm - 10 pm saturday - sunday: 9 am - 10 pm october tuesday - friday: 5:30 pm - 10 pm  saturday - sunday: 9 am - 8 pm.

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 143 boat rentals in huntington, ny, usa.

In addition to the best offers we have for boat and yacht charters in Huntington, NY, see also options available for rent in these nearby locations:

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Choose a Long Island Boat Rental from Sailo to visit Bay Hills, NY

This summer you have to visit the Huntington Bay - a charming region on the North Shore of Long Island, home of Bay Hills - one of the most popular beach resorts in Suffolk County.

It’s time to leave the stress behind and take the well-deserved sailing trip with your family. Sailo offers an top selection of boat rentals around Bay Hills NY, perfect for a family vacation, a corporate event, a romantic getaway or private parties.

With a beautiful Long Island boat rental from Sailo you will have a relaxing but adventurous day on the water at the same time. Boating enthusiasts recommend visiting Sand City Island, a great place to swim, sunbathe or just relax aboard. Finish your day with a quick snack and a cold drink at one of the many waterfront taverns in Bay Hills Beach.

Choose a Long Island boat rental with captain and have a luxurious sailing experience in Northport Bay You cannot go wrong with a boat rental to explore Bay Hills NY and the Hungtington Bay, either a comfortable sailboat or a fancy motor yacht – it is guaranteed that your sailing trip will be a one of a kind experience.

If you plan to explore other nearby locations, then Oyster Bay has to be on your list. 

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Sound Sailing Center

Long island sound sailing school and membership club.

Long Island Sound

Adventure awaits.

Be sure to consult Eldridges for the tide charts when planning your trip. Never try to fight the tide near the race, unless you want to spend hours observing Plum Island. Also note that the current inside and outside of Long Sand Shoal can be moving in opposite directions, less than 2 miles apart!

Heading East

Moving to the east on the Long Island side is Port Jefferson (18nm away). As you enter the harbor, to the right is an unnamed bay which is highly popular with sailors.

My father called it Conscience Bay , and we probably anchored there 1,000 times (or so it seems) in my youth. Given the prevailing SW breezes, it’s usually a nice reach to and from Norwalk. Takes 3-4 hours in a 36 footer, 4-5 hours in an under 30 boat generally. You can also go into the town at the head of the harbor and pick up a mooring or dock. Danforth’s Restraint is popular. The sand pit, to your port as you pull in, has some shallow spots (I spent one afternoon on one after the boat swung around). The winds are shifty. Best left to the motorboats that crowd in, but it is fun for kids to climb and play on the cliff’s. Anchor just outside the sand pit.

After Port Jeff , the next harbor is Mattatuck (38 nm away), a narrow creek with only about 5 feet of water on low tide. There is a little room to anchor at the head of the harbor. Well protected, but nothing great.

The Connecticut side has many great harbors. From Norwalk, the first harbor is beautiful Southport (6nm away). No room to anchor, and only about 6′ in the outer channel at low tide. Call the yacht club for a mooring.

Next is Bridgeport (12 nm away). There is plenty of room behind the breakwater, and Pleasure Beach really is nice, but few boats stop here except for Tugs. I have spent a few nights in Bridgeport, and if nothing else, it sure is easy to enter in the dark due to all the lights. Bridgeport is getting better, with the baseball stadium and new marina planned, and it will become a better destination in time.

Black Rock , just to the east of Bridgeport Harbor, there are lots of little shops in Captain Cove Marina. Sort of a mini Mystic Seaport. Great yard, nice people. Stay away if the breeze does not have a westerly component, due to the treatment plant to the east.

After Bridgeport is Milford Harbor (no room to anchor, not too much to do), and little Charles Island (18 nm away), which you can anchor behind. Often crowded with day trippers, not many overnighters.

After the New Haven breakwater (not as good a stop as Bridgeport, but ok), comes my favorite spot on the Sound, the Thimble Islands (30 nm away). The Thimbles are huge hunks of Granite, and look like a chunk of Maine dropped in the Sound.

There is good holding ground in the mud between the islands. Stay away from the marked power cables. Enter in the daytime. There are numerous confusing buoys marking the many reefs. Once your in, it’s beautiful, if you like Maine. Unfortunately, the islands are all privately owned, so no exploring.

Adjacent to the Thimbles is Branford Harbor to the east, and Sachems Head to the West. Given the numerous reefs in the area, plot your courses carefully in advance, watch the depth like a hawk, and use lots of compass bearing to check your location. GPS is useless for threading around the reefs and islands. Sachems Head has a fine yacht club, but no space to anchor. There is plenty of space in the large harbor north of Sachems head, which is the place to go if the Thimbles are full up.

Past the Thimbles is Guilford , which is one of the prettiest town greens in Connecticut, a short 10 minute walk from the harbor. Unfortunately, the channel only carries about 4′ at low tide.

After Guilford, there is Westbrook and Duck Island Roads , which has a breakwater with 6-9 foot depths to anchor behind. Fairly exposed, lots of tide. I prefer to head up to Old Saybrook , and stay at the Dock N Dine (50nm from Norwalk).

Given the two lighthouses and prominent breakwater at the mouth of the Connecticut River, it’s an easy nighttime approach. If you grab dinner (or pull in between midnight and 11:00 in the morning), there is no charge to lie alongside the pier. Great spot to switch crews or pick someone up. Next door is a beautiful and very expensive resort marina, with a very good restaurant.

Five miles up the river is Essex , with a fine downtown and the great Griswold restraint. The Gris has one of the finest collection of ships prints in the country, worth more than the restraint. Stay at the Essex Island marina.

Four nm up is the beautiful fresh-water Hamburg’s Cove , and three more miles up is Gillette Castle. Another three miles and you’re at the Goodspeed Opera House, which is right on the river, with a pier. Probably can tie up, call ahead.

After the Connecticut River, the next great spot is Mystic , with the world renown Mystic Seaport. The bridge into Mystic only opens a few times a day, so get the opening times in advance.

It’s wonderful to stay one or two nights and be able to walk the grounds after everyone else has left. If you are a member, the dockage is a pretty good deal. You can also walk north to the Mystic Aquarium, or south to town, both of which are worthwhile.

There are also some Islands off Noank that you can anchor behind. After Mystic, Stonington and Fishers Island are a few miles away. Fishers Island offers beautiful estates, and not much else. I’ve anchored in both the west and east harbors in the J44, but neither are especially deep.

Stonington is also lovely, and Dodson’s boatyard is as nice as they come. Another great spot to do crew transfers. The downtown is beautiful, lots of antique houses and great dining establishments.

Through Plums Gut , Long Island begins to get interesting, with Shelter Island a wonderful spot, although I normally hurry on through the Race or Watch Hill Passage to Block Island . Block Island is a great destination, truly out to sea, with enough to do to keep everyone happy. The biking and hiking trails are great, plenty of good restaurants, super beaches, etc. Try to stay a few days if possible.

Everyone knows Newport , but Narragansett Bay offers a vast selection of Harbors, Jamestown , East Greenwich , Wickford , Bristol (visit the Herrshoff Museum), and the Kickamuitt River , where I spent a Hurricane a few years ago. All fine cruising grounds.

Search continues for two boaters missing since crash off Old Saybrook Monday night

Published september 5, 2024 • updated on september 5, 2024 at 12:05 pm.

The search has resumed on Thursday morning for two men who have been missing since a boat crash in Long Island Sound off Old Saybrook on Monday night.

Nine friends were returning after spending Labor Day on Block Island when the 31-foot motorboat they were in hit a jetty around 9:15 p.m. Monday, according to the Department of Energy and Environmental Protection EnCon Police.

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Christopher Hallahan, 34, of Westbrook, was found dead in the vessel, according to the state Department of Energy and Environmental Protection. The Office of the Chief Medical Examiner determined that he drowned and ruled his death an accident.

Six other people who were on the boat were taken to the hospital and one of them is in critical condition, Connecticut Environmental Police Captain Keith Williams said Tuesday morning.

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Officials believe that person was driving the boat, but they have not confirmed that. Another of the six people was released from the hospital and two men are still missing.

The capsized boat was recovered from the river around 11:30 a.m. Tuesday.

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Several agencies, including police and fire crews from several nearby towns, the State Police Dive Unit, and a helicopter from the U.S. Coast Guard station on Cape Cod have been involved in the search for the missing men.

That search was suspended at sunset Wednesday before resuming on Thursday morning.

Officials have not identified the missing men but said the people who were on the boat have ties to the local community.

On Labor Day weekend in 2023, four people were hurt in a similar crash. A few weeks earlier, another boat hit the jetty at the mouth of the river and a man was hospitalized.

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Long Island ties run deep for Cole Brauer, 1st US woman to sail around the world alone

By pei-sze cheng • published march 7, 2024 • updated on march 8, 2024 at 7:47 am.

Cole Brauer made history as the first American woman to sail nonstop around the world by herself.

The 29-year-old, who came in second in the Global Solo Challenge, is an East Hampton native. Her teachers at East Hampton High School watched her heavily documented journey with awe.

"It brings pride to the whole school and whole community,” said principal Sarah Smith.

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"All the same things we are seeing with her now,” said video production teacher Jeremy Quitko, “Is what I saw in the classroom where she was on camera and also edited her own videos.”

Teachers and administrators remembered her determination and drive. She was voted most unique in the senior class, was on the track team, and a member of the Art Honor Society.

There was a sailing club at school, but ironically, Brauer did not participate — although her twin sister Dalton did. Brauer learned to sail when she lived in Hawaii, which kicked off a passion that she has been pursuing ever since.

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Brauer set sail in October and sailed 30,000 miles, starting from Spain, down the west coast of Africa, to Australia, and around the tip of South America before returning to the starting point.

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Brauer's 130-day journey was treacherous at times, facing 30-foot waves and hurricane-force winds. Cameras at one point showed how rough seas threw her across the boat, injuring her rib. Another time she was so dehydrated, she needed an IV, which she inserted herself.

On the TODAY show, she was asked how she managed to continue with the journey.

"There really is no option at that point you’re so far away from land, there is no rescue," said Brauer.

Adam Fine, the superintendent of East Hampton schools, used to be Cole’s principal and remembers a time when she stopped to help a stranger who got into a car accident.

“It was really indicative of her personality — there was no fear, somebody involved in the accident, she went over to help,” said Fine. “So when I watch videos of her putting in her own IV, I know she can handle these sorts of things.”

For current students who watched her journey, Cole is an inspiration.

“She obviously has the motivation and determination,” said sophomore Maya Taveras. “It’s nice to see her accomplish her goal.”

“It shows even if you come from a small town you can make a big impact on the world,” said Ryleigh O’Donnell, a senior, “Get your name out there and make a big difference.”

Celebrating Cole’s accomplishment has inspired administrators to recognize other graduates and their accomplishments.

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Sunfish Women's North American Championship to be held in Great South Bay

Barbara Meier is on a mission to race or sail her Sunfish in all 50 states. So far, she’s made 42, including Alaska.

On Friday, she found herself in Amityville, where she was gearing up to participate in the Sunfish Women’s North American Championship. The winner will go to the world championship in Ecuador next year and represent the United States.

Meier, 63, only started sailing three years ago and wasn’t expecting to win or even place high. But she was thrilled just to be racing among some of the top women sailors in the country. They came from as far as Washington state and Florida, and ranged from teenagers to women in their 70s who have been sailing for more than six decades. Several were previous national champions.

Gail Heausler, of Tampa, Florida, practices off Amityville in the Great South Bay on Friday for the North American Sunfish Championship. Credit: Newsday / Kendall Rodriguez

A practice race took place Friday in Great South Bay off the Dinghy Shop in Amityville, with the full competition set for Saturday and Sunday among some 50 competitors.

“There is no way I should be in a championship regatta,” said Meier, who currently lives in Sarasota, Florida. But the competition was open to anyone, though most were accomplished sailors.

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It was a sign of the camaraderie among the women sailors that she said she felt fully accepted and warmly embraced, as top sailors freely gave her advice on everything from how to rig her boat to how to sail upwind.

Another competitor, Libbie Tillman Fitzgerald of Bellevue, Washington, said, “Just sailing with women is unique,” adding that it creates a “female energy.”

The Sunfish is one of the most popular boats on the planet, with at least 500,000 of them produced since it fully came on the scene in the 1960s. It is a spinoff of the Sailfish, which is like a surfboard with a sail on it, originally used by lifeguards for rescues. Boat makers added a cockpit for comfort so people could sit more easily and, along with a few more features, came up with the 14-foot Sunfish.

Jim Koehler, owner of the Dinghy Shop who is hosting the championship and himself a top sailor, said people can learn to sail the relatively simple Sunfish in a day. But to get to the level of the top competitors involves a whole other range of skills, from figuring out water currents and wind shifts, adjusting sails and “hiking out” — that is, leaning off the boat when the wind blows hard.

The single-sail Sunfish is particularly appealing for women because you don’t necessarily have to be big or brawny to sail it, he said. “Women can sail the boat with authority,” he said. “It’s not a male-dominated or strong, big adult boat.”

Lee Parks, a former national women’s Sunfish champion from Newport, Rhode Island, who has been sailing for six decades, said she was thrilled to be at the regatta in Amityville.

“This is going to be phenomenal,” she said. “We love the Great South Bay. It’s just perfect for Sunfish.”

Susan Tillman Berg, whose mother was a Sunfish women’s national champion and whose father was a member of the 1976 U.S. Olympic sailing team, said the Dinghy Shop is nationally known in sailing circles and was an ideal place to host the race.

“This is like an icon in the sport,” she said. The trophy for the championship is now named after her late mother, Linda Tillman.

Meier said she had a good day on the bay Friday, as she piles up sailing experiences in places including Lake Tahoe — on both the California and Nevada sides. If she makes it to all 49 states on the mainland, she said, she plans to fly to Hawaii and rent a Sunfish there so she can claim all 50 states.

Bart Jones has covered religion, immigration and major breaking news at Newsday since 2000. A former foreign correspondent for The Associated Press in Venezuela, he is the author of “HUGO! The Hugo Chavez Story from Mud Hut to Perpetual Revolution.”

'I'm going to try to avoid it' A trip to the emergency room in a Long Island hospital now averages nearly 4 hours, data shows. NewsdayTV's Virginia Huie reports.

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Staten Island Ferry boat owned by Pete Davidson, Colin Jost is on the move: Here’s where it’s going next

• Updated: Sep. 07, 2024, 12:06 a.m.
• | Published: Sep. 06, 2024, 11:29 a.m.

The decommissioned John F. Kennedy ferryboat, which was purchased by Staten Island celebrities, Colin Jost and Pete Davidson, will be home to a Tommy Hilfiger fashion show. (Staten Island Advance) Staten Island Advance

• Erik Bascome | [email protected]

STATEN ISLAND, N.Y. -- The Staten Island Ferry boat purchased by borough natives and Saturday Night Live stars Pete Davidson and Colin Jost is wading into new waters -- the world of high fashion.

The decommissioned John F. Kennedy ferry, which the two comedians purchased for $280,100 through an online public auction in 2022 , will serve as the venue for one of the annual flagship events of New York Fashion Week, which runs from Sept. 6 through Sept. 11.

First reported by Women’s Wear Daily, the iconic, orange vessel will be docked at Pier 17 and used to host Tommy Hilfiger’s fashion show on Sunday, Sept. 8, with Jost expected to be in attendance for the event.

“New York City is the birthplace of the American dream, and the Staten Island Ferry represents the gateway to self-expression for so many across history,” Hilfiger told Women’s Wear Daily.

“By hosting this year’s show aboard the MV John F. Kennedy, a recently decommissioned ferry, we will celebrate the quintessential New York City landmark, while writing [the fashion brand’s] nautical-inspired codes firmly into the vessel’s iconic legacy,” he added.

Davidson and Jost, alongside comedy club owner Paul Italia, initially had plans to turn the decommissioned boat into a live entertainment venue, but unexpected repair and remediation costs have delayed those plans.

ABOUT THE JFK FERRY

Prior to its retirement, the John F. Kennedy was the oldest remaining boat in the Staten Island Ferry’s active fleet, having first been commissioned in 1965.

The boat, which was the first Staten Island Ferry with diesel-electric propulsion machinery, measures nearly 300 feet in length and is capable of carrying over 3,000 passengers at a time.

The John F. Kennedy was popular among riders for its outdoor promenades and extended foredecks, features that have been incorporated into the newest class of Staten Island Ferry boats.

The vessel has had its vacant slot in the active fleet filled by the SSG Michael H. Ollis, the first of the three new boats constructed by Eastern Shipbuilding Company.

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