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  • Since our establishment in 1953 by Lawrence Hartge in Annapolis, MD, we have been proudly serving boating enthusiasts on the stunning Chesapeake Bay with exceptional service and unparalleled expertise.
  • Lawrence Hartge, a visionary and passionate boater, laid the foundation of our company with a simple yet powerful mission: to offer a full-service boat buying experience that surpasses expectations.
  • His dedication to the craft and his love for the Chesapeake Bay set the tone for our company's values, which we continue to uphold to this day.
  • Over the years, we have become synonymous with excellence in the Mid-Atlantic region.
  • Whether you're a seasoned sailor or a first-time buyer, we understand the unique needs and preferences of our customers, and we strive to match them with the perfect vessel.
  • Our extensive selection of boats caters to all tastes and budgets. From sleek powerboats to classic sailboats, we offer a diverse range of options that will suit any boating enthusiast.
  • Whether you're looking to buy, sell, or simply enhance your boating experience, we are here to make your dreams a reality.
  • Come visit us and tour our boats at Pier 7 Marina in Edgewater, MD.

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

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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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Schooner Woodwind

2024 Sailing Season is coming! See you April 13, 2024!

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Welcome Aboard!

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

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

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Make your sailing experience a memorable one! Sail away with us!

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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?

annapolis sailboats

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?

annapolis sailboats

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.

annapolis sailboats

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 Two American Sailing Seminars 

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

Cruising Essentials with Captains Andy and Lisa Batchelor

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Join Captains Andy Batchelor and Lisa Batchelor on a journey to understanding cruising and living onboard for extended periods. Getting ready for a life of cruising for yourself and your boat can offer an exhilarating yet potentially bewildering journey. Lisa and Andy Batchelor bring their extensive expertise in sailing and cruising to the forefront in this all-encompassing in-person workshop. They aim to demystify, educate, and ignite inspiration. Lisa and Andy hold the distinction of being American Sailing Master Instructors and have authored numerous acclaimed American Sailing cruising guidebooks. They are the principal contributors to the ASA 106 Advanced Cruising & Seamanship manual. Whether you’re an aspiring cruiser, a weekend sailor, or nurturing ambitions of circumnavigation in the future, this seminar is meticulously crafted to equip you with the wisdom needed to strategize, gear up, and triumphantly actualize your cruising aspirations.

Details: Saturday, October 14, 2023 1:00 – 4:00 PM Eastern Time THE FEDERAL HOUSE – 22 MARKET SPACE, ANNAPOLIS MD 21401

How To Buy An Offshore Cruising Boat with Captain John Neal

John Neal

Captain John Neal knows a thing or two about offshore sailing with over 400,000 offshore miles under his belt, including six Cape Horn roundings plus expeditions to Antarctica, Africa, Australia, and Spitsbergen. During this seminar, you will acquire insights into the present condition of the boat market, strategies for maneuvering through the purchasing procedure, and the requisite know-how for securing insurance in an environment that is continually evolving. Benefit from the firsthand advice of seasoned professionals within the industry on effectively pinpointing the perfect vessel tailored to your preferences. This seminar is designed to guide you through the process of handpicking a yacht ideally suited for cruising while also delving into a comprehensive examination of prevailing market instances encompassing prices and patterns.

Details Saturday, October 14, 2023 1:00 – 4:00 PM Eastern Time THE FEDERAL HOUSE – 22 MARKET SPACE, ANNAPOLIS MD 2140

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. 

Thomas Lighthouse in Chesapeake Bay near Annapolis

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Annapolis Sailboat Show 2022.

2022 United States (Annapolis) Sailboat Show: Preview Guide

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Table of Contents

Every October, the Chesapeake Bay enjoys an influx of new and salty sailors as they gather at the premier sailing event in the country. The United States Sailboat Show , also known simply as the ‘Annapolis Sailboat Show,’ attracts hundreds of exhibitors including boat builders, sailing schools, charter companies, boating gear manufacturers, boating magazines, and local marine businesses.

This year, the show will take place October 13-17 with a special preview day on Thursday. Attendees come from all over the country and even all over the world to see the latest sailboat technology in a place where you can’t beat the nautical vibe. Annapolis is a sailor’s paradise and if you’re planning to visit, why not charter a sailboat and get in some time on the water or even do a sleep-aboard and dodge the crowded hotels? Here at Boatsetter , we have a significant Annapolis fleet with options and experiences to choose from.

Here’s what to expect from the 2022 United States Sailboat Show:

  • When: October 13th – 17th, 2022
  • Where: City Dock (Annapolis, MD)
  • Cost: $25 (at gate), $22 (at door), $10 (for children of ages 7-12), FREE (for kids 6 and under)
  • Enhance your boat show experience with a boat rental : Book here

Own a Boat? Let your boat pay for itself. List, rent, earn — Only at Boatsetter.

United States Sailboat Show.

New Boats and Exhibitors

Among the exhibitors this year, you’ll be able to check out:

  • Fountaine Pajot
  • And so much more!

Whether you’re looking for a racing monohull, a luxury catamaran, the latest electronics, technical apparel, or a charter vacation, you’ll find it at the Annapolis boat show.

VIP Experience Sponsored by La Victoire Finance

Enjoy the VIP Red Carpet Lounge with exclusive seating, mouth-watering catering, and craft cocktails. Pricing is $175. Add reserved parking for a $25 upcharge.

Sailing Channels Booth

Check out the Sailing Channels Booth to meet boating influencers:

  • Sailing La Vagabonde
  • Sailing SV Delos
  • Sailing Doodles
  • Parlay Revival

And more! Stop by to learn more about boating life from their personal stories.

Educational Opportunities

New to boating? If you’ve come to learn, you won’t be disappointed.

  • The Take the Wheel interactive workshop is sponsored by Jeanneau sailboats and Sail Away catamarans and it’s your opportunity to learn on and off the water.
  • Also, kids 11-15 can get on the water with the Junior Captains program designed to make them enthusiastic sailors while adults can take the wheel of two monohulls and two cats to see what best fits their personality.
  • The very popular Cruisers University is already open for registration and most of the program will be held at the Historic Inns of Annapolis on State Circle. There are dozens of classes led by expert speakers. Learn diesel mechanics, weather for cruisers, marine electrical systems, anchoring, and more. University prices include educational materials, expert instruction, breakfast and lunch, evening activities, a one-year basic BoatUS membership, and admission to the show(s).

Register early for any of the above because they sell out fast.

US Sailboat Show 2022.

Door Prizes

Pusser’s Painkiller and door prizes – what’s not to love? Purchase advance tickets online or sign up at the show to win special door prizes including a seven-day charter in the British Virgin Islands with The Moorings.

Brokerage Cove

If you’re looking for a pre-owned sailboat, visit Brokerage Cove on the other side of the Spa Creek Bridge. It’s an easy walk from the main show. Alternatively, you can take a water taxi to this floating marina in St. Mary’s Cove that’s full of boats for sale, ready for immediate cruising.

Pro Tip: Call up a babysitter or fur babysitter; pets and strollers are not allowed at this event.

The Annapolis show is an internationally acclaimed event, recognized as one of the world’s most comprehensive and prestigious sailboat shows. Even if you aren’t boat shopping, the atmosphere in Annapolis that weekend is for anyone who loves the water.

You can discover more boating events like the US Sailboat Show at Boatsetter’s Boating Guides & Resources !

Boatsetter is a unique boat-sharing platform that gives everyone — whether you own a boat or you’re just renting — the chance to experience life on the water. You can list a boat , book a boat , or make money as a captain .

Explore All Available Boats for Rent near Annapolis, MD

Zuzana-Prochazka

Zuzana Prochazka is an award-winning freelance journalist and photographer with regular contributions to more than a dozen sailing and powerboating magazines and online publications including Southern Boating, SEA, Latitudes & Attitudes and SAIL. She is SAIL magazines Charter Editor and the Executive Director of Boating Writers International. Zuzana serves as judge for SAIL’s Best Boats awards and for Europe’s Best of Boats in Berlin. 

A USCG 100 Ton Master, Zuzana founded and manages a flotilla charter organization called Zescapes that takes guests adventure sailing at destinations worldwide. 

Zuzana has lived in Europe, Africa and the United States and has traveled extensively in South America, the islands of the South Pacific and Mexico. 

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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: the beginning of April to the second week of October.

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

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

*A 30-minute sailing assessment is required of all new customers. The assessment costs $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 six 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 half-hour overdue.

  • KeelBoat Club Members: Click HERE to jump to KBC Rainbow rental’s booking and information page. You can also click the drop-down labeled “KeelBoat Club Rentals” located under the “KeelBoat Club” tab. Please have your membership ID ready.

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

Want to stay in the know about Annapolis Sailing School? Sign up for our new monthly newsletter here to receive information on classes, events, schedules and more!

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The Liberté

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A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

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Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

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The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

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Annapolis Boat Shows

Every year, Annapolis City Dock (affectionately dubbed “Ego Alley”) is transformed into a boater’s paradise when the Annapolis Powerboat Show (Oct. 5-8) and Annapolis Sailboat Show, presented by West Marine (Oct. 12-15) head into town.

Tens of thousands of boaters and enthusiasts descend on Annapolis to see the latest and greatest boat models, maritime tech, and boating products. Come experience this fall adventure at the world’s largest in-water boat show and stay for the weekend in Annapolis, near BWI, or the Arundel Mills Entertainment region .

Annapolis Powerboat Show

October 3 – 6, 2024.

The United States Powerboat Show features everything from luxurious motor yachts to trawlers, high-performance boats, and offshore fishing vessels. There are also family cruisers, center consoles, and inflatable and trailerable powerboats. Vendors' tents line the waterways, selling everything powerboat enthusiasts could dream of and offering boating lessons , rentals , and more. 

Aerial image of the US Power Boat Show in Annapolis from 410Films

Annapolis Sailboat Show

October 10 – 14, 2024.

What better place than the Sailing Capital of America to host the world's most impressive sailboat show? Spend the day hopping from one vessel to another before stocking up on sailing essentials from the many vendors in attendance, offering everything from high-tech navigational equipment to outboard motors.

Find more information on parking options for  Annapolis Powerboat Shows .

Where to Eat During the 2018 Spring Sailboat Show

Plan Your Trip

Transportation, things to do, your guide to the fall boat shows this october.

Explore Annapolis & Anne Arundel County for some unforgettable sights, events , entertainment , and dining .

You’ll definitely be ready for a comfortable place to rest your head after a full day of boat-hopping. Luckily, Annapolis & Anne Arundel County offer a wide range of accommodations . Stay downtown at one of the lovely boutique hotels or bed and breakfasts , or try one of the many options (at all price points) throughout Annapolis and Anne Arundel County. Have an early flight home? Try one of these hotels near BWI for easy access to the airport.

Explore the Arts

While you’re in town, be sure to take in some of the rich cultural experiences the city has to offer. From outdoor concerts to world-class theaters to chic art galleries , Annapolis has something for everyone to enjoy. 

Where to Eat

Although you might be here for the boats, know that Annapolis is a true culinary destination as well! Of course, you know Maryland has some of the freshest crabs and seafood around, but there is also every type of cuisine you could desire: Italian , Thai , Mexican , French , and so much more! Experience the perfect  brunch spots , enjoy some fresh   oysters, or take a trip by car or boat to one of the outdoor dining options around the county.

Evening Entertainment      

As you walk through the historic streets of Annapolis, you are likely to hear the tunes of your favorite local musicians wafting out of local pubs and restaurants. Certainly, Annapolis is known for its live music scene . If you feel like dancing, be sure to hit up the hot spots along Ego Alley and Main Street for DJs and drinks late into the night. For something a little different (and family-friendly) take one of the city’s nighttime walking tours, including ghost tour options (if you dare!)

Or if glitz and gambling are more your speed (I’m looking at you, power boaters), hop over to  LIVE! Casino & Hotel . Whether it is gaming, dining, or live music – you’ll find it at LIVE!

So whether you’re a go-fast power boater, savvy sailor, or even just boat-curious, the boat shows are a spectacle not to be missed. Buy your tickets now and make it a weekend!

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Forbes Yachts

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The perfect boat.

We sell the boats that allow you to effortlessly connect your passion for yachting to the sea, bringing your world one step closer to perfection. We are not just another Annapolis boat broker. By listening, understanding and educating, we help you make the right choice for the best yachting experience. 

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As professional yacht brokers we handle each transaction with a tailored plan engineered to produce results. With two generations in the marine industry we are the Annapolis boat brokers who can expertly advise our clients on everything from making an informed offer to vessel documentation.

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We are Annapolis boat brokers,  but we are also boaters and have a breadth of experience ranging from boat building and offshore cruising to commercial vessel operation.

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annapolis sailboats

A Celebration of Sailing at the Annapolis Spring Sailboat Show

Click here for a pdf of the original press release.

Sunrise at the Spring Sailboat Show

FOR IMMEDIATE RELEASE | Annapolis, Maryland | April 11, 2024 | Annapolis Boat Shows will be hosting the 2024 Annapolis Spring Sailboat Show April 26-28 at City Dock in Annapolis, MD. The show will be open to the public 10 a.m.-6 p.m. on Friday and Saturday, 10 a.m.-5 p.m. on Sunday. This year, there are expected to be more than 40 sailboats on display and over 100 total exhibitors. New to the show is the No Wake Zone – a space to house local wine and spirits tastings, live music, and an outdoor-wear fashion show. This year’s show has a renewed emphasis on getting new people into sailing with programming for both kids and adults. The show also serves as a gateway to the US Sailing Capital, with showgrounds only steps away from historic downtown Annapolis. Tickets can be bought for $18 online, $20 at the gate, and $11.25 for service members.

Boats in the Show

Smaller in volume than the fall show, the spring show offers an impressive range of boats. There will be a selection of electric yacht tenders, racing dinghies, daysailers, cruisers, and multihulls with LOAs ranging from 11’ to 60’ ( see full list ).

A notable outlier is the 157’ Pride of Baltimore II. The recreation 19 th century Baltimore clipper may not be available for purchase but, like all the boats featured at the show, attendees are welcome to climb aboard and explore.

Couple Inspects Vessel

Exhibitors & Entertainment

The 2024 Annapolis Spring Sailboat show will feature over 100 exhibitors – a quarter of which are displaying boats. The remainder offer a wide variety of goods and services that cover every facet of the marine sphere and beyond ( see exhibitor list ).

No Wake Zone

New to the show this year is the No Wake Zone – an area set aside for attendees to relax while highlighting local brands and artists. The outdoor lounge area has been furnished by Gabby & Summer Classics. Live music will be performed by local musician Sean Owen. Samples of Maryland-made bourbon, whiskey, vodka, gin, rum, and wine will be offered, and bottles will be available for purchase. On Saturday, fashion shows will be held to showcase active wear from Shanks Golf Apparel and Made Plus shoes ( read more ).

Attendees Enjoying Drink Tasting

Education & Newcomer-Oriented Programming

Free seminars.

The show’s series of free boating seminars, presented by BoatUS, covers a wide variety of topics relevant to all skill levels. All attendees are welcome to participate in expert-led, 45-minute classes that cover crewing aboard tall ships, docking and dining, point-to-point racing, and more ( see full schedule ). Below is a selection of seminars:

  • Rules of the Road with Captain Deb Marlor (Friday, 1:15-2 p.m.)
  • Essential Knots and How to Tie Them with Ben & Teresa Carey (Saturday, 10:15-11 a.m.)
  • Line Handling and Safe Docking with Ben & Teresa Carey (Saturday, 11:15 a.m.-12 p.m. | Sunday 1:15-2 p.m.)
  • VHF Etiquette on the Water with John Herlig (Saturday, 1:15-2 p.m.)
  • Empowering Women Behind the Wheel with Captain Deb Marlor (Saturday, 3:15-4 p.m.)

First Sail Workshop

Presented by the American Sailing Association, First Sail Workshop is a hands-on class that affords people aged 18 and up the opportunity to establish the foundations of sailing. The workshop is divided into a 45-minute classroom session and a 90-minute, on-water lesson aboard a Beneteau First 22. The class is priced at $65 per person and includes admission to the show and a one-year membership to BoatUS.

Start Sailing Now Reunion

SpinSheet Publishing will be holding a meetup at the Spring Sailboat Show on the morning of Sunday, April 28 for the sailors it has interviewed over the past 10 years as part of SpinSheet’s Start Sailing Now campaign. Start Sailing Now shares the stories of people who started sailing as adults and aims to encourage other adults to take up sailing. Show-goers who are at the show as it opens on Sunday morning are invited to join these sailors (made identifiable by their Start Sailing Now badges) huddled around the SpinSheet booth swapping stories and offering encouragement.

Ben Carey Leads Seminar

Youth Sailing

Along with a selection of dinghies, the Annapolis Spring Sailboat Show has a lot to offer young sailors and their parents. A notable addition to this year’s show is the Rooster sailing gear trailer. There will be a wide variety of sailing apparel available for purchase as well as knowledgeable staff to direct parents as to what gear their child needs and proper fitting. Loaner life jackets will be made available at the show entrances courtesy of BoatUS.

Youth Sailing Panel Discussion

All are invited for a youth sailing panel discussion and Q&A session on Saturday, April 27 at 10:30 a.m. Whether parents have already registered their child for a youth sailing program this season or simply wonder whether such a program would be right for their family, they won’t want to miss the casual and lively panel discussion planned for families who have questions about youth sailing. Moderated by SpinSheet staff, this session will touch on all the essentials that families need to know to get their youngsters sailing. A group of coaches, parents, and recent college sailors will discuss the gear kids need, safety, costs, how kids progress to bigger boats, and more. More generally, panelists will discuss how sailing fosters life skills, problem-solving, and independence. Children are encouraged to attend accompanied by an adult.

Kids Enjoying Spring Sailboat Show

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  • LaVictoire Finance

Visit the  2024 Annapolis Spring Sailboat Show Media Assets Library  for information, materials, and high-resolution copies of the images included in this press release.

To sign up for media credentials to the 2024 shows visit the  ABS Press Center .

Requests and inquiries should be directed to Ryan Gullang:  [email protected]

Tickets are on sale now!

refresh the page.

For Sale "sailboats" in Annapolis, MD

  • 1985 Point Jude 16 Sailboat and Karavan Trailer $2,495 Essex
  • 1980 O’Day 22 Sailboat and 1994 Karavan Trailer $995 Essex
  • IRWIN 27 SLOOP RARE CLASSIC $2,750 Annapolis galesville
  • Sail FREE once a week $1 SEVERNA PARK
  • 1986 C&C 25 mkII $4,900 Annapolis
  • S2 6.7 Grand Slam 22 Ft $3,500 Annapolis
  • Catalina 27 $10,000 ANNAPOLIS
  • 1968 Chippendale Fireball Sailboat 5132 $1,000 Aliquippa, PA
  • Kayak sail Kayaksailor $600 Severna Park
  • Catamaran Arc 21 $3,000 Annapolis
  • 1970 Alberg 30 $10,000 Lancaster
  • kayak sail Pacific Action Sail $275 Severna Park
  • HUNTER 170 SAILBOAT AND TRAILER $3,000 YORK, PA.
  • Whisker Pole 14 ft $200 Mayo
  • 1968 35’ Dickerson Ketch $3,333 North East
  • catamaran $7,500 Annandale
  • 1979 36’ Moody $30,000 Baltimore
  • 1978 Cape Dory 25 Sailboat For Sale $9,000 Annapolis, MD
  • 1981 S2 8.0 26 ft $4,000 Selby on the bay
  • Sail 33.5 Endeavour $16,000 St Michaels
  • 1977 American AG Sailboat with trailer $4,500 Germantown md
  • 29er Skiff $8,400 Annapolis
  • Dyer Dhow Mainsail $400 Annapolis
  • 1977 O'Day 22 Sailboat w/Trailer, new 4-stroke, 2 full sets of sails $1,900 Arnold
  • 19' Cape Dory Typhoon Daysailer $7,800 Berlin
  • Optimist - McLaughlin $2,250 Annapolis
  • Optimist - Winner 3D Star $4,000 Annapolis
  • J80 50% share $12,500 Annapolis MD
  • Trinka 10 Dinghy $2,000 Annapolis md
  • Sailboat Package $3,900 Annapolis
  • Sailboat 1990 35 feet $39,000 Severna Park
  • Morgan 36 Sailboat $20,000 Annapolis
  • 1979 Pearson 28 $9,500
  • Chesapeake Light craft Southwester Dory $15,250 Annapolis
  • sailboat Package $3,900 Annapolis
  • Seafarer 39 $19,000 annapolis, Md
  • 1989 Hunter 33.5 $25,000
  • Bristol 30 - Outfitted for blue water $14,500 West River
  • 16' AFC Sailboat w/ Trailer $800 Annapolis
  • International 470 sailboat $750 Washington
  • Shellback sail/row dinghy $2,100 downtown Annapolis
  • 10' Trinka Sail, Row, Motor w/ Custom Galv. Trailer rated for 4 people $1 Va. Beach , VA.
  • 1993 22" CUSTOM CAT SLOOP $53,000 Deltaville
  • Wanted Sailboat $0 annapolis
  • Catalina 36 tr $40,000 Annapolis
  • 1984 Oday 23 Sailboat $6,500 pasadena md
  • Free sailboat Grampian 25 $0 Edgewater, MD
  • Freedom 28 Cat Ketch $11,500 Solomons MD
  • 1987 O’day 35 $19,500 Edgewater
  • Ericson 38 Sailboat - Liveaboard Ready $19,999 Titusville
  • 23' Com-Pac Pilothouse 2012 with Trailer $54,500 Annapolis
  • 41' Bristol 41.1 Center Cockpit $69,900 Annapolis
  • Tremolino II Trimaran Sailboat $6,500 Arnold
  • 1981 Endeavour 40 $83,500
  • project sailboat & trailer $1,750 nw balto co
  • 1976 Hunter 25 $1,500
  • 1975 Cape Dory 25' Sailboat $860 Pasadena
  • crusing / performance sail boat Formosa 43 $39,900 Annapolis/ sassafrass river
  • 1965 O’Day Daysailer $1,499 Annapolis
  • Sailboat Hunter 25ft with Solar Panels $8,000 Galesville
  • Frank Beken Sailboat Sailing Vintage Photography Prints Framed Art $140 Odenton
  • Literally New symmetrical Spinnaker in Perfect condition $250 Edgewater
  • Boat Slip next door to Pirates Cove Restaurant $10,000 Galesville
  • Stainless Railing $0 Annapolis
  • Genoa Sail for Sailboat $500 Annapolis
  • Sailboat Parts and Equipment $1 West Chester PA
  • Lehr 5 hp outboard (long shaft) $350 arnold
  • S2 9.2A $12,750 Annapolis
  • Lead weights $65 Annapolis
  • Beneteau First 33.7 $75,000 Plattsburgh
  • sailboat trailer $2,800 Mount Jackson
  • Volvo Marine Diesel Engine Parts $15 Annapolis
  • Tenderly $6,500 Annapolis
  • Lightning Sailboat $2,500 Annapolis, MD
  • BRITISH SEAGULL ENGINES $1 Murray Hill, Annapolis
  • Sail Boat Pearson 35' 1980 $5,000 Machodoc Dalgren
  • 1992 Seaward Fox day sailor w/trailer $5,500 Davidsonville/Annapolis MD
  • 25' O'Day Sailboat w/ outboard & trailer $3,500 Deale, MD
  • Sailboat $1,250 Annapolis
  • 1977 American AG Sailboat with trailer $3,500 germantown md
  • Grand Soleil 50 $165,000 Millville NJ
  • Pro-Furl Roller Furling $150 Elkridge
  • Stainless Dinghy Davits! $1,100 Severna Park
  • Sailboat Parts $1 West Chester
  • Prijon Kodiak Sea Kayak $725 Severna Park
  • 2-SLIPS REMAINING located on Spa Creek, Annapolis $0 Annapolis
  • Facnor 2500 Top Down Furler and Spinnaker $1 Near Annapolis, Maryland
  • 26' Pearson Sailboat $400 Annapolis

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Where to Book Booze Cruises of All Kinds in D.C.

Seasonal offerings on the Potomac include tailgating excursions to Nats Park, sunset Champagne on the dock, and everything in between

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annapolis sailboats

This spring, D.C. docks are home to a surge of drinking vessels designed for every occasion, vibe, and price point. A returning line of retro motor boats are apparently the ticket to getting engaged, with seven proposals out on the water last year. Want to watch dolphins give birth on the Chesapeake this summer? One hotel offers an excursion for that. And a fancy sailboat manned by a fine-dining chef pairs tasting menus with French wines.

Soak up monumental views along the Potomac River, drink in tow, with this running list of bookable boats.

Sea Suite Cruises

Co-founders and Arlington natives Jack Walten and Jack Maher’s first BYOB paddle pub debuted in 2018. Six years later, their supersized fleet is made up of 13 boats bobbing around Mid-Atlantic waterways (in D.C., Baltimore, Annapolis, and Richmond), plus floating tiki bars. And a landlocked bar born in Clarendon is the muse for one of their hottest new bookings this season:

Whitlow’s on Water

Now the largest boat in Sea Suite Cruises’ fleet, the 48-passenger tiki tour is the product of a fun new partnership with Whitlow’s owner Jon Williams. His iconic Clarendon dive moved to Shaw, but its original tiki rooftop on Wilson is reincarnated as a floating bar. “Whitlow’s on Water has taken the [Potomac] by storm,” says Sea Suite’s Jack Walten, noting it’s pretty much sold out almost every Saturday through the summer. Diehard Whitlow’s regulars, which includes the “Jacks,” have a familiar face on board: a former bartender from its Clarendon days handles the liquid lineup. Standard mixed drinks join beers, wines, High Noon seltzers, orange crushes, and rum punches. There’s also a selection of pub grub (sandwiches, wings, etc.) sourced from Whitlow’s.

annapolis sailboats

Two TVs air “whatever people want to watch,” he says, which has included everything from March Madness to the Bachelorette (bachelorette parties are popular bookings, after all). As are corporate teams, birthdays, Whitlow’s fans, and even 50-year wedding anniversaries. Individual tickets are also available, to “mix and mingle like you would in a normal bar,” he says. Sea Suite caters to Washington Nationals fans with a traffic-free cruise from Georgetown to the Yards Marina, docking just in time to walk over for the first pitch. “Tailgating on a tiki boat, it doesn’t get better than that,” he says.

Price: Ticket tiers start at $24 and up for daily options that include individual or group sightseeing tours, tiki taxis, private charters, or “Nats Sailgate” ( book online).

Where: Pick-ups and drop-offs in Georgetown in front of Fiola Mare ( 3100 K Street NW ) and Yards Marina by District Winery (1492 4th Street SE )

annapolis sailboats

Retro Boat Rentals

Vintage runabout boats from Sinatra’s time were retro-fitted with electric motors, so having a romantic or intimate conversation is highly possible. It’s no wonder there were multiple (seven) proposals out on the water last year, reports Sea Suite. Each four-top fiberglass beauty sports a different color and name (Gladys, Bonnie, and Violet).

Price: $175-$225 for 1.5-hour tours; BYO drinks and food

Where: Wharf to the Washington Channel

annapolis sailboats

Potomac Tiki Club

D.C.’s “first tiki cruise” lets patrons buy booze on board, or opt for an $8 corkage fee for wine and Champagne. BYO food or purchase small snacks.

Price: $45-$60 for parties of 8 to 18 out of Georgetown. A smaller thatched-roof sibling out of Navy Yard fits six and runs $350-$425. Both last 1.45 hours.

Paddle Club Cruises

Sea Suite Cruises’ fleet that started it all is a pontoon pedal boat outfitted with 10 cycle stations (or just let the motor power the party). BYOB (just no hard liquor) or purchase on-board beverages like canned Cutwater ($4-$8.50).

Price: $35-$55 for groups of 8 to 16 for 1.45-hour tours

Where: Docks from the Wharf, Navy Yard, and Georgetown

Sea Table DC Aboard Cru Classé

Chef and sommelier Troy Knapp makes Michelin-level menus on his luxury sailboat Cru Classé. Back at the Wharf for its third year , the detail-oriented captain brings fine-dining to the dock with artfully plated courses, decadent floral arrangements, seafaring table settings, and French wines he pours himself. Knapp also mans other Wharf vessels for parties of six or more, partnering with Nautiste to offer dining excursions with his catering company Curated.

Choose from three different experiences this season (book via TOCK ):

annapolis sailboats

  • Cruise Experience (April through October): Set sail for up to three hours while enjoying four to six courses comprised of ingredients from local farms and fishermen. Complemented by prestigious wine pairings. Starting at $430 per guest
  • Dockside Experience (April, May, September, and October): Savor four to six courses with sommelier-selected wines while docked at the Wharf’s marina for up to two hours. Starting at $180 per guest
  • Oyster Sails (June, July, and August): Enjoy local bivalves, freshly shucked by an oyster expert on board, alongside specialty accompaniments. Paired with Champagne or prestige white wine. Starting at $225 per guest

Where: Docks at the Wharf ( 650 Wharf Street SW )

Pendry on the Potomac

annapolis sailboats

The most baller option of the bunch by far, the Wharf’s luxe Pendry hotel offers guests a captain-chartered Aviara cruise that’s available to the public for the first time. Parked in its own slip right out front of the Southwest Waterfront hotel, onboard food and beverage offerings include Champagne and caviar service supplied by Pendry’s culinary team. Bar selections, beer or wine, and appetizers can be customized, depending on the parties’ preference. Excursions near and far include round trips to Nationals home games and an all-day adventure to the Chesapeake Bay to spot marine life. As it turns out, dolphins use the Potomac and Bay as a nursery to birth their calves — a rare event that happens from mid-June to mid-August when the water is warmest. Kicking it up at full speed (35-40 knots), hat-holding patrons will jet downstream through Old Town, Fort Washington, and Mt. Vernon and (hopefully) see the annual occurrence.

Price: $3,600 (3 hours); $4,600 (4 hours); $6,000 (6 hours); $7,800 (7 hours) for up to six; reserve here .

Where: Outside of the Pendry ( 655 Water Street SW ) at the Wharf Marina

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  4. Sailboats in a Marina at Sunset, in Annapolis, Maryland. Editorial

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  6. Sunrise Among the Sailboats at Annapolis Maryland Photograph by Bill

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    Preowned racing, cruising, dailsailer, and multihull sailboats for sale, including Beneteau, Burger , Cal, Catalina, C & C, Cheoy Lee, Columbia, Coronado, Corsair ...

  23. A Celebration of Sailing at the Annapolis Spring Sailboat Show

    FOR IMMEDIATE RELEASE | Annapolis, Maryland | April 11, 2024 | Annapolis Boat Shows will be hosting the 2024 Annapolis Spring Sailboat Show April 26-28 at City Dock in Annapolis, MD. The show will be open to the public 10 a.m.-6 p.m. on Friday and Saturday, 10 a.m.-5 p.m. on Sunday. This year, there are expected to be more than 40 sailboats on ...

  24. annapolis for sale "sailboats"

    For Sale "sailboats" in Annapolis, MD. see also. 1970 Alberg 30. $10,000. Lancaster 1968 35' Dickerson Ketch. $3,333. North East Cal 39 MKII. $22,500. Annapolis 1980 O'Day 22 Sailboat and 1994 Karavan Trailer. $995. Essex 1985 Point Jude 16 Sailboat and Karavan Trailer ...

  25. Where to Book Booze Cruises of All Kinds in D.C.

    D.C.'s "first tiki cruise" lets patrons buy booze on board, or opt for a $8 corkage fee for wine and Champagne. Bring your own food or buy small snacks. Price: $45-$60 for parties of 8 to 18 out of Georgetown. An additional thatched-roof boat out of Navy Yard fits six and runs $350-$425. Both last 1.45 hours.