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Chesapeake Bay Sail or Power Boat Charters & Rentals? There's a better way with the Chesapeake Boating Club.

Whether you're a beginner or an old salt, you'll find a range of high quality boats to meet your needs..

Boating should be flexible, fun and affordable! This is what we believed when we opened for business in 1992 in the Historic Eastport section of Annapolis, and that commitment has made us what we are today - The #1 flexible boat sharing program on the Chesapeake Bay. Let us help you experience the thrill of boating at a fraction of the cost of ownership.

     ◊  Sailing       ◊  Powerboating        ◊ Instruction

26 boats waiting .

Choose the right boat for any adventure - Sail and Power from 17'- 36'

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Located only .5 miles from the heart of Annapolis, and .3 miles to open water.

Boating Seminars

Check out some ONLINE boating educational seminars that are being offered by our J World coaches in the off season:

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Testimonials and latest news:

Recent improvements that have been completed in 2022 for Chesapeake Boating Club boats: Bottom jobs and topsides cleanings on... Sea Swirl (powerboat) Windtrip V (J/105) Calypso's Spell (J/105) Caper (J/32) Wyanoke (J/32) Grady White (powerboat) Liberty (Albin 28 powerboat) Wired (Club J/80) Seesaw (J/105) August 21, 2022

Read the Chesapeake Bay Magazine review of The Club

Join the Club: Tim Sayles, Editor of Chesapeake Bay Magazine, on the Boat Club Concept

Annapolis Boat Club

All the Fun Without the Hassles of Ownership

About the club.

Experience Fun Boating Adventures

At Annapolis Boat Club, we believe that the best way to explore Annapolis and its beautiful surroundings is by boat. Discover hidden coves, and breathtaking sunsets as you navigate through the sparkling waters. Our fleet of well-maintained boats ensures a safe and comfortable journey, allowing you to focus on the pure enjoyment of boating.

We Have a Boat for Everyone

With a wide range of boat options and expertly maintained boats, we make it easy for you to get out on the water and create unforgettable memories. Whether you’re a seasoned captain or a novice sailor, our club offers something for everyone.

Boost Your Boating Skills

Whether you’re a beginner or looking to enhance your boating skills, our experienced instructors are here to help. Join our training programs and gain the knowledge and confidence to navigate the waters like a pro. From basic safety courses to advanced boating techniques, we offer comprehensive training classes by an authorized licensed captain.

“This club compares to no other. The customer service and friendly people make things so easy for us to enjoy the water. Plus the marina amenities are included. The kids love the pools”

Kathy Miller

Why Join Our Boat Club?

With 3 locations to choose from, our team provides members with great boats that are safe and reliable for our members and guests.

You get to use marina amenities, the pools, workout room and Wi-fi. Plus member only special events and parties. And most important, a fun and experienced staff to help you enjoy the experience.  

Whether you’re curious about the program and need to talk with someone, or would like to view the boats and marina, we’re here to answer any questions.

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The Only Boat Club that Includes Marina Amenities.

Pool – Workout Room – WiFi – Annual Parties & Events – A Great Friendly Staff

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Classic Sail Charters

Private sailing charters in maryland, choose your location, annapolis, md.

May - October

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• Most Popular!

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Hour Glass 2.5 Hours
• Users Up to 6 Passengers

Your Dream Adventure Awaits

Catering to clients seeking a unique, private sailing adventure for up to six passengers, we offer world-class sailing yachts, decades of experience, and 5-star service to ensure that your charter is truly memorable. All our charters are for private parties, so you can have it your way. is required. 

Charters Feature

Sunset Cruises

Daily Sails

Weekend Cruises

Milestone Celebrations

Marriage Proposals

Family Adventures

Check-out what our Guests say about us! ★★★★★

Capt. Nate & Payton were great! We did an engagement shoot on the boat and they were unbelievably helpful. They were extremely accommodating to the photographer and worked to position the boat perfectly as the sun was setting. Siena is a beautiful boat and the west river is idyllic. Can't recommend enough.

Captain Tony was great host and helped us have a fantastic experience. He even taught my husband some sailing skills, which allowed me to relax, have some snacks and drinks. Boat was clean and very well maintained. He has a strong commitment to saftey and is very knowledgable about sailing. Highly encourage others to book a trip with him.

My fiancé and I are both from New England and grew up by the water, so we knew we wanted a nautical setting for our engagement photos. We had a fabulous time with Classic Sail Charters on the beautiful Siena! Captain was so helpful in offering to angle the boat this way and that for better light and even raising or collapsing sails. We'll definitely be back!

My husband I along with our two grown children (in their 30's), had a wonderful day with decent wind in July sailing at times to 15 knots! Captain Tony was accommodating and friendly. He had a variety of snacks and beverages on board and encouraged participation in sailing the boat as well as relaxing in the sun or shade! We will definitely do this again and we're thinking of also offering this as a gift to my parents who also love to sail.

This past Friday, we joined Capt. Tony aboard the Licentia for an afternoon sailing the Bay. We had a great afternoon sailing and motoring (we lost the wind) around the Bay and through the Annapolis Harbor. Capt. Tony is very knowledgeable, friendly, and helpful. He has loads of sailing experience and all enjoyed his sea stories. Would we go again? Absolutely - planning a trip for next May.

Four of us sailed with Captain Tony on 2 different trips - one afternoon and one morning. Both days were fantastic and relaxing and lovely. The 2nd trip we lost the wind eventually so motored around the Bay and Annapolis and Tony gave us some history and stories. He is delightful and skilled and we had a terrific time. We will definitely plan another trip one of these day.

Sailing Charters aboard the 'PINTITA' out of Annapolis & Baltimore

Make your next getaway a sailing adventure on the Chesapeake Bay!

Are you planning a birthday or anniversary celebration, planning a proposal, getting married or renewing your vows, or just want to enjoy the Annapolis or Baltimore skyline with a cold beverage while sailing?  Help raise and trim the sails, navigate, man the helm or simply take in the experience and sights while relaxing with a cold beverage. Come see what the allure of sailing is all about. The professional Captain and Crew of the ‘ PINTITA ’ can help make your next adventure a memorable one. 

We are currently booking private sailing charters for up to 20 passengers! 

We ask that you continue to support your local businesses and this Veteran owned small business needs your support and patronage.  Please book your private sailing charter soon for your next friends, family, and or corporate outings.  We are looking forward to harnessing the wind and creating memories with you.

Pla n to join us for the U.S. Navy Blue Angels in Annapolis during Commissioning Week in May, 2024

See our Charters page from the menu above

Call us now to book your getaway:

443-510-5756

The ‘PINTITA’ is perfect for:

Bachelor & Bachelorette Parties

Engagement Proposals

Anniversaries

Alumni Events

Company Events

Team Building

We offer many charters to meet your needs.

The 'PINTITA' Sailboat is licensed for groups of up to 20 persons! She has an all weather enclosed cockpit to keep you dry from passing showers! She is designed to make your outing as entertaining and comfortable as possible.

The PINTITA

Come sail the chesapeake bay..

Join us in Annapolis & Baltimore.  We hold a current USCG Certificate of Inspection for Private charters, meaning that she is inspected in her construction, equipment, and maintenance to rigorous federal standards.

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How to Make the Most of This Year’s Annapolis Sailboat Show

By: Zeke Quezada, ASA American Sailing , Boat Shows

A shiny new sailboat will make your heart race, your palms sweat, and trigger the butterflies in your stomach. Stand on the boat of your dreams, and you’ll feel a powerful and intense feeling of affection, attraction, and emotional connection.  Amid the lively Annapolis Sailboat Show, I absorb the inspiration and ponder my own sailing journey. Around, dreams blossom—a vibrant tapestry of aspirations. Witnessing the joy of a boat purchase nearby, I sense the essence of possibility. Dreams meet reality on the dock in Annapolis as old goals are achieved, and new goals are set.

Up and down the rows of the show, you see bright flags and shiny vessels capturing your every glance. At last count, over 400 vendors attend the boat show, exposing you to the newest and coolest objects of desire. How great would it be to outfit your boat with all-new electronics? Imagine new sails to replace those tired but storied rags on your sloop. Can you ever have enough jackets or gloves or winch handles?

The Annapolis Sailboat Show is a spectacle for sailors and lovers of all things sailing. Everywhere you turn, conversations fill the air about vacations in the Med or anchors that can hold fast in all conditions or the dream to sail the world. 

The Annapolis Sailboat Show allows us to dream while seeking inspiration and motivation and engaging in some infatuation.

Why Should You Go to the Annapolis Sailboat Show?

Heading to Annapolis for this popular event is a sailor’s hall pass to enter a world of maritime innovation and inspiration. Nestled amongst a vibrant gathering of industry experts and enthusiasts, expose yourself to the unveiling of the latest vessels, cutting-edge technologies, and nautical gear. From connecting with like-minded individuals to exploring diverse sailing options, the sailboat show offers a firsthand experience of sailing’s finest offerings. Engaging seminars, networking opportunities, and a palpable atmosphere of a sailor’s passion further enrich the experience. Whether seeking a new vessel or simply immersing oneself in the sailing lifestyle, a boat show equips sailors with insights, knowledge, and connections that amplify their sailing journey.

10 Reasons to Attend the Annapolis Sailboat Show

• Dare to Dream about a New Boat: The show features a diverse and wide selection of sailboats, from small day-sailers to luxurious yachts. Whether you’re a novice sailor or an experienced boater, you’ll have the opportunity to explore and compare different types of sailboats, from various manufacturers and in different sizes.
• Hands-On Experience: Unlike traditional boat shows, the Annapolis Sailboat Show often allows attendees to step aboard many of the boats on display. This provides you with a chance to get a real feel for the boats, check out their features and layouts, and even discuss their design and performance with knowledgeable exhibitors.
• Educational seminars to open up your horizons: The Annapolis Sailboat Show typically hosts a series of seminars, workshops, and demonstrations on a wide range of topics related to sailing, boating safety, navigation, maintenance, and more. These educational opportunities can enhance your understanding of sailing and help you develop your skills. Maybe you will find that sailing destination you never knew was possible actually is well within your ability!
• Meet the rockstars and influencers of the sailing world: The show brings together boat manufacturers, dealers, and industry experts. This is a great opportunity to engage in conversations with professionals who can provide insights into the latest trends, technologies, and innovations in the sailing world.
• Networking with other sailors: If you’re passionate about sailing, this event provides an excellent platform to connect with fellow sailing enthusiasts. You can share experiences, exchange tips, and potentially make new friends who share your interest in boating.
• Exclusive deals that turn dreams into reality: Boat shows often offer special pricing, discounts, and promotions that may not be available at other times of the year. If you’re in the market for a sailboat or sailing-related equipment, the show could be an opportunity to find some great deals.
• Discover the latest tech and products: In addition to sailboats, the show usually features various exhibitors showcasing the latest sailing gear, equipment, accessories, and technologies. You can discover new products that could enhance your sailing experience.
• Scenic Location: Annapolis, known as the “Sailing Capital of the United States,” provides a picturesque backdrop for the event. The historic maritime town offers a charming atmosphere with waterfront views, local restaurants, and cultural attractions.
• Fun and Entertainment: Beyond the boats and equipment, the Annapolis Sailboat Show often includes entertainment, live music, and social events that make the experience enjoyable for attendees of all ages. Find a karaoke bar and sing with sailors until the early morning hours!
• Inspiration: Even if you’re not in the market to buy a boat, attending the show can be a source of inspiration for future sailing adventures. It’s a chance to immerse yourself in the sailing world and dream about future voyages.

In summary, the Annapolis Sailboat Show offers a unique opportunity to immerse yourself in the world of sailing, explore a wide range of sailboats, learn from experts, and connect with fellow sailing enthusiasts. Whether you’re a seasoned sailor or just curious about the boating lifestyle, the show can provide a memorable and enriching experience.

Learn from Experts in These LIVE American Sailing Seminars 

American Sailing is hosting a series of live seminars during the Annapolis Sailboat Show that are sure to help you achieve your sailing goals.

SECRETS OF SUCCESSFUL CRUISING

HOSTED BY GIO & JULIE CAPPELLI

Pelagic Blue Cruising Services, Owners

✓ Expert Sailors and Instructors

✓ Diverse Expertise

ANNAPOLIS, MD

FRI, OCT 11, 2024

For cruisers and aspiring cruisers intrigued by the secrets to setting sail with confidence and joy, this live seminar will address and navigate the challenges at sea, covering coastal and offshore passages, self-sufficiency in boat maintenance, and relationship dynamics with your crewmate(s).

HOW TO SAIL AROUND THE WORLD

HOSTED BY JAMIE & BEHAN GIFFORD

Sailing Totem

✓ Seasoned Circumnavigators

✓ Cruising Experts and Authors

Join experienced circumnavigators and cruising coaches Jamie and Behan Gifford for a comprehensive, information-packed session on How To Sail Around The World. During this live seminar, Jamie and Behan will be sharing tips, tricks, and shortcuts for launching a safe and successful circumnavigation.

CRUISE WITH CONFIDENCE

HOSTED BY LISA & ANDY BATCHELOR

Kinetic Sailing, Owners Sail Solomons ASA School, Founders

✓ Award-Winning Sailing Instructors and Authors

✓ Distinguished Cruising and Passagemaking Background

SAT, OCT 12, 2024

Discover the key to successful extended cruising. Whether you’re just dreaming of setting sail or already living the liveaboard life, Lisa and Andy Batchelor, ASA Master Instructors, will offer invaluable insights and practical advice during this live seminar. From boat equipage to sail trim and docking, learn how to prepare yourself to cruise with confidence and clarity.

GUIDE TO BOAT BUYING

HOSTED BY JOHN NEAL

Log Of The Mahina, Author

✓ Expert Sailing Trainer and Author

✓ Extensive Offshore Experience

During this live seminar, learn what the current state of the boat market is, how to navigate the purchase process, and the experience needed to gain insurance in the ever-changing times. Hear inside tips from industry experts on how to find the right boat for you as they walk us through the procedures of selecting a sailing yacht that is ideal for cruising while analyzing current market examples of prices and trends.

HOW TO TROUBLESHOOT & FIX COMMON DIESEL ENGINE PROBLEMS

HOSTED BY NIGEL CALDER

Marine Diesel Engines, Author

✓ Innovative Marine Engineer

✓ Prolific Author and ABYC Veteran

SUN, OCT 13, 2024

Unlock the secrets of diesel engine troubleshooting in this live seminar with Nigel Calder, author of best-selling book Marine Diesel Engines. Gain practical insights into diagnosing and fixing common issues like overheating, power loss, and more. Perfect for current or future boat owners seeking to enhance their understanding of diesel engines and resolve problems efficiently.

PRACTICAL ELECTRICAL SYSTEMS TROUBLESHOOTING FOR BOATERS

Dive into common boat electrical system issues with Nigel Calder as he outlines simple step-by-step troubleshooting techniques that can be safely conducted by any boat owner, including using a multimeter. Live seminar attendees will learn how to head off common battery and systems failures and rapidly identify the majority of electrical problems seen on boats. The goal of this seminar is to raise your confidence levels of boat owners, given today’s increasingly electrically-loaded and complicated boats.

Make Plans To Attend The Annapolis Sailboat Show

You might find yourself admiring the couple embarking on their journey with a new Beneteau, sensing the allure of their adventure. And you’ll share a knowing smile with the young enthusiast donning a fresh Helly Hansen jacket, recognizing the spirit of exploration and discovery they embrace. You will leave the boat show with a newfound motivation to escape into the fantasy of sailing. Spend enough time with fellow sailors, and their energy is intoxicating.

If you ever needed the gentle nudge to do more with your love for sailing and the sailing lifestyle, you can bet that a couple of days in Annapolis will push you in the right direction. 

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Servicing Annapolis Maryland and the greater Chesapeake Bay waterfront area.

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Bringing performance and recreational sailboats, equipment, apparel, and repairs to Annapolis and the greater Chesapeake Bay!

It's time to gear up for spring and summer sailing!!!

About annapolis sail works, our mission.

As a veteran-owned and operated small business, we strive to serve the local sailors and performance water sports athletes of the Chesapeake Bay with the best boats, equipment, repairs, and expertise to make competitive sailing and other watersports accessible and sustainable for all.

Veteran-owned Small Business

 A veteran-owned and operated company, Jake Crespin and Jeff Daigle established Annapolis Sail Works in 2023 to serve the Chesapeake Bay waterfront community with high-quality sailboats, equipment, repair services, and expertise. Jake and Jeff are both avid lifelong sailors with extensive sailing and marine industry backgrounds and a passion for boats, performance, and recreational sailing. Jeff is a retired career Coast Guard Helicopter Pilot and a Texas Maritime Academy graduate, where he was captain of the varsity sailing team. Jake is a career Marine Corps Infantry Officer and graduate of the U.S. Merchant Marine Academy, where he sailed on the Kings Point varsity dinghy and offshore teams. Both owners race various classes of dinghies, keelboats, and offshore boats. They founded Annapolis Sail Works to make high-performance and recreational sailing on the Chesapeake Bay more accessible and sustainable by bringing a full-service dinghy shop back to Annapolis, MD. 

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Rainbow 24 Sailboat Rental

No trip to the sailing capital of America would be complete without getting out on a sailboat. Our fleet of Rainbow 24s provides a safe and fun experience for those looking to have a relaxing time on the water. Feel free to bring lunch and turn it into a picnic as you pass by the sights with the wind carrying you along.

Rentals are available during our sailing season, from the beginning of April to the end of October.

Weekdays – $158 (+taxes and fees) for a full day or any portion of a day between 9 am – 4 pm.

Weekends & Holidays – $225 (+taxes and fees) for a half-day between 9 am – 12:00 pm OR 1:00 pm – 4:00 pm

*If you are a new customer, you are required to complete a 30-minute sailing assessment. The assessment cost $30 in addition to the rental fee.

Reservations

A reservation is needed to ensure that a sailboat is available when you want to go out. At least two adults are required on a rental boat, one of whom must be a qualified sailor. Up to 6 people are permitted on a rental boat; no children under 5 years of age are allowed. No pets are permitted.

A late fee of $75 will be charged per every half-hour overdue.

To reserve a Rainbow Rental, please call 410.267.7205 or email   [email protected]

KeelBoat Club Members: Click the button below to jump to the KeelBoat Club Rainbow Rental’s page. You can also click on the “KeelBoat Club” tab and visit the drop-down labeled “KeelBoat Club Rentals”. Please have your membership ID ready.

KeelBoat Club Rainbow Rentals

Our Rainbow 24 sloops have proven to be nimble, fast, and forgiving. Designed by Sparkman and Stephens specifically for Annapolis Sailing School, the boats are ready to please both novice and experienced sailors. The substantial fixed keel (1100 lbs), cuddy cabin design, and large cockpit combine to produce a boat that is stable, dry, and comfortable.

Qualified Renters

At least one person in the rental party needs to have an ASA 101 certification or its equivalent. New customers must complete a sailing competency evaluation with us prior to their first rental. Renters are required to rig and de-rig their boat. The Rainbows do not have engines, so sailors must be able to depart and dock under sail.

If you need a refresher on rolling and flaking our sails, check out our how-to page here !

Sailing Area

Rentals are restricted to an area close enough to the school so that help can reach you quickly in an emergency situation. Boundaries, determined by management, are subject to change depending on weather and water conditions at the time of your rental. Please understand that going beyond these boundaries makes quick retrieval of the boats difficult in case of emergency. Late returns of boats due to venturing beyond the boundaries will result in late fees. If a renter goes outside the prescribed sailing area and needs to be retrieved, there will be a fee of $75 and the renter will be unable to rent with us in the future.

Sailing is entirely dependent upon wind and weather. We recommend that renters check marine.weather.gov three days before the rental date to see what the forecast is for that day. If small craft advisories or worse are in effect at the start of the rental, the rental may be postponed, canceled, or otherwise restricted at the discretion of the management. In that case, the rental can be re-booked at no additional cost. In low wind situations, you will need to plan your sail so that you can be back at the dock on time.

Cancellations

Rental reservations are charged at the time of booking. Rescheduling within three calendar days of the originally scheduled start of the reservation will result in a $50 rescheduling fee per occurrence. Cancellations made within two calendar days of the scheduled day of the reservation will receive no refund. Refunds are not available for lack of wind.

The boats are covered by insurance. Please inform management of any damage that occurred during the rental. The Lessee has no liability for repairs. However, Annapolis Sailing School is not responsible for personal injury or damage to other boats. You should check your own insurance coverage before sailing.

Other Restrictions

• Children on board must be at least 5 years old
• No alcohol allowed on boats
• No pets allowed on boats
• No swimming off the boats allowed
• No anchoring
• Boats are not permitted to dock at other marinas or facilities other than Annapolis Sailing School

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Here’s what you need to know about the return of the annapolis sailboat show at city dock this weekend.

The three-day spectacle kicks off Friday at 10 a.m. featuring about 35 sailboats that will be moored around City Dock downtown, said Annapolis Boat Shows General Manager Sheila Jones.

The Sailboat Show was last held in Annapolis in 2019. In 2020, both shows were canceled and last year the two events were combined into one four-day event on Kent Island.

Last weekend the powerboat-focused Bay Bridge Boat Show drew thousands of visitors over four days. Though she couldn’t give an exact number, Jones said attendance was on par with 2019.

“This is our first year back after two years away,” Jones said. “We’re having good weather and we’ve had good presale tickets.”

The spring show, and its counterpart in the fall, are the only all-sails shows in the country, Jones said.

Here’s what to know about the Annapolis Sailboat Show:

The Annapolis Spring Sailboat Show hours are 10 a.m. to 6:30 p.m. on Friday and Saturday, and 10 a.m. to 5 p.m. on Sunday.

Exhibitors and activities

There are more than 100 on-land exhibitors this year, up from 84 in 2019, Jones said.

A few new exhibitors will be displaying their wares this year, including CoBoaters, a social network for sailing aficionados; Electric Yacht, which offers electric boat motors, batteries and chargers; and BMW, which will be test-driving for some of its electric vehicles.

There will be educational opportunities and free seminars throughout the weekend. Cruisers University will offer classes in marine weather forecasting, traditional navigation techniques, heavy weather sailing and other classes. An offshore emergency medicine class will guide participants through a range of medical techniques on the open seas. Daily seminars on earning a captain’s license, docking and line handling are also available.

The show will also feature door prizes, including four tickets to the United States Sailboat Show this fall, and a tasting tent with alcoholic beverages sponsored by Breakthru Beverages Maryland.

Tickets can be purchased at www.annapolisboatshows.com . General admission is $20 per day.

VIP tickets are $85. A handful are still available for Friday and Sunday. Saturday is sold out. VIP tickets include reserved parking for $15 at the Donner Parking lot at 120 Compromise St.

Children ages 12 and under are free.

No exchanges or refunds.

Pets and strollers are prohibited at the event due to concerns of falling in the water or being a tripping hazard.

The closest parking garage to City Dock is the Noah Hillman Garage, located two blocks away.

The garage will be open to attendees through the end of the Sailboat Show on Sunday. The garage will close to parking for demolition on Monday with the construction of a new parking structure expected to take 14 to 16 months.

Other parking options can be found at annapolisparking.com .

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Annapolis Spring Sailboat Show

April 26-28, 2024, join us for the spring boat show in america's sailing capital, annapolis, md..

Are you itching to get on the water? Jumpstart the boating season with the Annapolis Sailboat Show this April 26-28, 2024 .  Annapolis Boat Shows , a leading management company, has been producing these in-water demonstrations since 1970, drawing over 150,000 people from all over the world to the Chesapeake Bay who want to see the latest and greatest in boats and related gear.

The Annapolis Spring Sailboat Show

The Annapolis Spring Sailboat Show takes place Friday, Saturday, and Sunday, April 26-28, at the Annapolis  City Dock . Set in the seaport of Annapolis, it displays catamarans, monohulls, racing boats, and inflatables - with over 100 new and brokerage yachts. Check out the vessels and spend some time shopping for the latest equipment, including electronics, clothing, and other accessories. The show runs from 10 am to 6 pm on Friday and Saturday and from 10 am to 5 pm on Sunday. General admission is $18; children under 12 are free.

Or indulge in an exclusive VIP Experience for $85/ticket. Your VIP ticket includes Boat Show admission and access, with unlimited entry, into the VIP Lounge located inside Latitude 38 Waterfront Restaurant. The lounge includes a full bar starting at noon, continental breakfast, buffet lunch, and afternoon appetizers. Valid for one day only.

April 26 - April 28

Friday: 10:00 am - 6:00 pm

Saturday 10:00 am - 6:00 pm

General Admission ~ $18  ($20 at the gate) Children under 12 are free

For more details, be sure to visit their website . Fair winds and following seas!

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Sailing Season is Here. Join Us for a Sail!

Sunset Sails

Welcome Aboard our two beautiful, wooden 74-foot schooners,  Woodwind  and  Woodwind II , for a true sailing experience in Annapolis, Maryland.

Sunset is a favorite time for a sail on the  Woodwinds . The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight.

Let our captain and crew make your trip an enjoyable and memorable experience.  Our bar is stocked with wine, beer and bubbly, including a nice selection of local, independent craft beers available for purchase.

History Mondays

A guided tour exploring the history of the Chesapeake area, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard. Early May – September.

Beer Tasting Tuesdays

Sample while you sail! Each month we feature a different brewery from the Chesapeake area. A representative from the brewery comes aboard and teaches you about beer. You will taste 3 samples of beer and then you can purchase full beers from the brews that you enjoyed the most. Early May through September. Schedule of Breweries.

Wednesday Night Races

Join the crew and race Woodwind vs. Woodwind II every Wednesday night from late April through late August.  There can be up to 100 other sailboats racing in the Wednesday Night Regatta sponsored by the Annapolis Yacht Club. Wednesday is the night to “Party Like A Sailor”.

Thursday, Friday, Saturday, and Sunday

There is no specific entertainment on these days of the week. There is so much to see as we sail by the United States Naval Academy and into the Chesapeake Bay. Let the crew serve you that favorite beverage as you relax watching the sunset over the city skyline.

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The Annapolis Spring Sailboat Show is the perfect time to climb aboard new and preowned boats, catch up with experts, stock up on boating essentials, and explore what National Geographic Adventure Magazine calls one of the top waterfront destinations in the country .

April 25 - 27, 2025 City Dock, Annapolis, MD

Friday, April 25 10:00am – 6:00pm

Saturday, April 26 10:00am – 6:00pm

Sunday, April 27 10:00am – 5:00pm

Ticket Options

General admission.

The Annapolis Spring Sailboat Show is located at City Dock in Annapolis, MD.

GPS: 1 Dock Street, Annapolis, MD 21401. 

View In Google Maps

Parking is  available in the parking garages in downtown Annapolis . Be sure to plan ahead as parking garages downtown fill up fast.

EXPLORE OUR TOWN

The Annapolis Boat Shows have always enjoyed calling Annapolis home. With beautiful brick-lined streets filled with art galleries, apparel, antique shops, and specialty boutiques, downtown Annapolis has plenty of fun for every visitor. Visit the many shops along Main Street and Maryland Ave, book a historic walking tour with  Watermark , tour the U.S. Naval Academy, and enjoy a glorious sunset cruise aboard the  Schooner Woodwind.  Learn all about the great things to do in our hometown and what  events  are happening during the shows with the help of  Visit Annapolis and Anne Arundel County .

The Pink Crab, at 152 Main St., will be offering special promotions on tables outside of their store. Be sure to stop by!

Reserve Parking

Known as the “Sailing Capital of the World”, Annapolis’s maritime history, nautical culture, and fun atmosphere make it the perfect location for boat shows. When guests have finished exploring the floating docks and shoreside exhibit areas at the Spring Show, downtown restaurants, shops, and galleries open their doors to these sailors looking to extend their stay. Make your plans now and book accommodations. Learn more about how to Visit Annapolis and Anne Arundel County .

• Boat Show Hotels
• Downtown Annapolis Hotels
• Arundel Mills & BWI Airport Hotels
• Are pets allowed on show grounds? No, animals are not allowed inside the show due to safety and health reasons unless it is a certified service animal.
• Are strollers allowed on show grounds? No, strollers are not allowed inside the show due to safety issues. Please park your stroller in the designated stroller parking area.
• Should my child wear a life jacket? Yes, we recommend all children wear life jackets for their safety.
• Will the show be open if it rains? Yes, the boat show happens rain or shine.
• Can I scan my ticket from my phone? Yes, you do not need to print out your ticket. All tickets may be scanned from your phone.
• Are backpacks allowed in the show? Yes, backpacks and bags are allowed.
• If I leave the show, am I allowed back in later? Yes, you will receive a hand stamp that will allow you to re-enter the show without your ticket.
• Can I bring food or drink into the show? Yes, you may bring food and drinks into the show.

Tickets are on sale now!