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 fall & winter 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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Your trusted full-service boat buying experts.
- 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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48 S River Rd S, Edgewater, MD 21037
(410) 267-8181
© 2023 All Rights Reserved
- New Inventory
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Catalina 385
Catalina 425
Catalina 445
Welcome to sail annapolis | annapolis, maryland, authorized dealer for:.
Located on the Annapolis Waterfront – Premier Sailboat Dealer for Catalina Yachts & Com-Pac Yachts & True North Power. Serving the Chesapeake Bay & Mid-Atlantic Region
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Featured Boats
2000 Tartan 3500
Price: $125,000
Annapolis, Maryland
2016 Catalina 385
Price: $270,750
Edgewater, Maryland
1998 Catalina 400
Price: $140,000
2000 Hunter 410
Price: $118,000
Baltimore, Maryland
2021 Hanse 508
Price: $696,000
2024 Catalina 355
Price: Request Price
2024 Catalina 425
2024 Catalina 445
2025 True North 34 Outboard Express
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- Annapolis: 410.263.8234
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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
Corporate Events
Special occasions, adventure & entertainment.
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.
One Great boat, two great locations
About the boat.
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 Sailboat Show
October 10-14, 2024
City Dock, Annapolis, MD
Until the Show
Sailors from around the globe gather in beautiful downtown Annapolis every October for the Annapolis Sailboat Show.
This annual celebration of sailing features floating docks lined with sailboats from manufacturers around the world. Multihulls, monohulls, cruisers, racers, sailing dinghies and more. Show tents line the shore, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs and more.
Seasoned and novice sailors alike are invited to expand their horizons and connect with fellow sailors during this internationally acclaimed show.
October 10-14, 2024 City Dock, Annapolis, MD
Thursday, October 10 10:00am to 6:30pm
Friday, October 11 10:00am to 6:30pm
Saturday, October 12 10:00am to 6:30pm
Sunday, October 13 10:00am to 6:30pm
Monday, October 14 10:00am to 5:00pm
What to Experience
VIP Experience
Educational Opportunities
2024 Exhibitors
The Sailboat Show features a large selection of sailboats, seminars, marine gear, accessories, and apparel.
Full list of boats on display
Full list of all service exhibitors
Full list of all product exhibitors
All Exhibitors
See who is exhibiting at the show
Tickets are on sale now!
"Seriously Fun"
Learn to Sail the Annapolis Way
Adult Sailing Lessons
Youth Sailing Lessons
Join KeelBoat Club
Rent a Sailboat
Evening Sailboat Charters
Try Sailing
Which course is right for me.
I want to be able to operate a vessel I already own or intend to buy.
I intend on renting or chartering sailboats in the future.
I want to explore the art of sailing and am looking for a great experience.
I'm looking to learn at my own pace with personalized private instruction.
Sailing is an Experience to be Enjoyed Over a Lifetime
We provide a community at the Annapolis Sailing School for your ongoing growth and enjoyment. We offer day sailboat rentals, adult sailing, KeelBoat Club Membership, KidShip sailing, powerboat lessons, and events at our beautiful location on Bembe Beach.
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Captained and Bareboat Charters in Annapolis, Maryland
The Chesapeake Bay is among the world’s top cruising and sailing destinations. A true American treasure, the Bay delivers a long enjoyable sailing season from early Spring to late Fall, with over 11,000 miles of shoreline to explore. From quiet, unspoiled anchorages, to historic seaside towns like St. Michaels and Oxford, to the vibrant ports of Baltimore and Annapolis, the Chesapeake Bay offers something for everyone.
Our docks in historic Eastport overlook the celebrated city of Annapolis and the Naval Academy. Take a short stroll or dinghy ride into town and enjoy the quaint shops and world-class restaurants before heading out on your Chesapeake Bay adventure.
Charter with Waypoints Annapolis to Experience:
- Daily, Weekend, and Week-Long Charters
- Skippered, Bareboat, and ASA Certification Charters
- New Luxuriously Appointed Fountaine Pajot Sailing and Motor Catamarans, Dufour Sailing Monohulls, Jeanneau Sailing Monohulls, and Jeanneau Powerboats
- Yachts Equipped with Air-Conditioning and Generators
- Provisioning and Personal Concierge Services
An Insider’s Viewpoint
“How would we describe the perfect cruise from Annapolis to St Michaels? Talk to Susan and Traci at Waypoints and hire Mike to be your captain and chef extraordinaire! Booking was easy and Dark Star was the perfect venue for our sail on the Chesapeake. We were blessed with beautiful weather and we never lacked in getting the details we needed quickly when we asked questions and made requests. We launched the boat from their very accessible location on the Eastport side of Spa Creek. They helped us navigate parking and Waypoints had people help us with our luggage. We can’t say enough good things about our experience. They exceeded our expectations!” Julie M.
“If you are looking for a Five-Star full-service charter experience and marina, look no further than Waypoints Annapolis. The boat was in mint condition and the service at the Marina was exceptional. Annapolis is a beautiful historic city with great restaurants and a fun nightlife for those who want to spend an evening onshore.” Mike
“This may be the best charter company I have ever used. Fantastic customer service, wonderful, perfectly maintained boats, price competitive, perfect location right on the Severn next to Chart House, boat choice from small to large.” Sandy
“Phenomenal company, team, and experience, from start to finish! Waypoints Annapolis offers the finest yachts for charter and boat-as-business opportunity we’ve ever seen!” Karen
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Sailing Season is Here. Join Us for a Sail!
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IMAGES
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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. Shop our selection of performance Opti, ILCA, 420, FJ, and RS sailboats, parts, and apparel. We also offer a full line or recreational sailboats ...
Find new and used sailboats for sale in Annapolis, including boat prices, photos, and more. For sale by owner, boat dealers and manufacturers - find your boat at Boat Trader!
Your Trusted Full-Service Boat Buying Experts. 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 ...
2024 Catalina 445. Price: Request Price. Annapolis, Maryland. .Annapolis Sailboat and Powerboat Dealer for Catalina Yachts and True North. Sail Annapolis is a boat broker in Annapolis Maryland MD.
Annapolis Sailyard is the oldest yacht brokerage in the Maritime Republic of Eastport in Annapolis, Maryland.. For nearly five decades we have been providing high-quality service and expertise in yacht purchase and sales for both sailboats and power boats. We have long term working relationships with multiple highly distinctive yacht manufacturers. At the Sailyard, we are experienced sailors ...
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 ...
Find Sail boats for sale in Annapolis. Offering the best selection of boats to choose from.
Motorized yachts are more common than sailing boats in Annapolis with 163 powerboats listed for sale right now, versus 160 listings for sailboats. Yacht prices in Annapolis. Prices for yachts in Annapolis start at $17,930 for the lowest priced boats, up to $3,999,700 for the most expensive listings, with an average overall yacht value of ...
Pricing*. 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 ...
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 ...
Annapolis Sailboat Show. October 10-14, 2024. City Dock, Annapolis, MD. Days: ... Minutes. Until the Show. Sailors from around the globe gather in beautiful downtown Annapolis every October for the Annapolis Sailboat Show. This annual celebration of sailing features floating docks lined with sailboats from manufacturers around the world ...
750 Boucher Avenue, Suite 205. Annapolis, Maryland 21403. Get Driving Directions. 443.716.7965. Mid-Atlantic Service, Now Available in the Heart of Maryland and the Upper Chesapeake! Learn More.
We provide a community at the Annapolis Sailing School for your ongoing growth and enjoyment. We offer day sailboat rentals, adult sailing, KeelBoat Club Membership, KidShip sailing, powerboat lessons, and events at our beautiful location on Bembe Beach. Relaxed, but careful. The kids had fun with level one and enjoyed it all so much.
Annapolis sailing cruises aboard the 74-foot Schooner Woodwind featuring sightseeing tours, sunset sails and entertainment cruises on the Chesapeake Bay. ... Join the crew and race Woodwind vs. Woodwind II every Wednesday night from April 27 through August 31. 100 other sailboats also race in the Wednesday Night Regatta. Wednesday's are the ...
Captained and Bareboat Charters in Annapolis, Maryland. The Chesapeake Bay is among the world's top cruising and sailing destinations. A true American treasure, the Bay delivers a long enjoyable sailing season from early Spring to late Fall, with over 11,000 miles of shoreline to explore. From quiet, unspoiled anchorages, to historic seaside ...
Guarantee the sail will not be booked for a private event. Participate in a breathtaking Parade of Schooners racing 130 miles from Baltimore's Inner Harbor down the Chesapeake to Thimble Shoal at the mouth of the Chesapeake Bay. Annapolis sailing cruises aboard the 74-foot Schooner Woodwind featuring sightseeing tours, sunset sails, multi-day ...
Exploring Annapolis, MD by boat! Enjoy Annapolis, MD's picturesque coastal area while sailing near the hottest tourist hotspots and local attractions. It's never too late for a yachting adventure, so use sail.me to rent a boat and admire scenic views from the comfort of a luxury yacht charter or private sailboat.
Sail boats for sale in Annapolis, Maryland 227 Boats Available. Currency $ - USD - US Dollar Sort Sort Order List View Gallery View Submit. Advertisement. Save This Boat. Balance 750. 2024. Request Price. Balance 750 Our Stunning new flagship is a ground-breaking high performance luxury adventure catamaran that offers both a forward cockpit and ...
Singles On Sailboats Inc. P.O. Box 5708 Annapolis, MD. 21403 Phone: (410) 798-4098 ...
Boats for sale in Annapolis Area, Maryland 1604 Boats Available. Currency $ - USD - US Dollar Sort Sort Order List View Gallery View Submit. Advertisement. Save This Boat. Schaefer 450. 2025. Request Price. The 450 Fly is the perfect complement to the Schaefer line, filling the gap between our 40 and 51 foot yachts. Enjoy space, comfort, and ...
Preowned racing, cruising, dailsailer, and multihull sailboats for sale, including Beneteau, Burger , Cal, Catalina, C & C, Cheoy Lee, Columbia, Coronado, Corsair ...
The most common engine type on powerboats in Annapolis is outboard, inboard, outboard-4S, inboard/outboard and other while the majority of powerboats listed have gas, diesel, electric and other fuel systems. Boat prices in Annapolis. The price for boats in Annapolis ranges from $4,279 up to $3,999,690, with an average boat value of $212,195.
Boats for sale in Annapolis, MD. see also. Exquisite, museum-quality Sovereign of the Seas. $13,000. Annapolis Maryland Quiet Waters Park Area Museum-Quality Scale:1:78 Model of the Sovereign of the Seas. $13,000. Annapolis Model Sail Boat for sale. $275. Annapolis Maryland near Quiet Waters Park ...
1989 Catalina 34 For Sale - $19,900 The Catalina 34 is a popular boat on Chesapeake Bay for many good reasons. It is very well constructed, with a great layout inside and out, with solid handling to take on some rougher weather, while keeping you comfortable.
Annapolis launches its fireworks from a barge in Annapolis Harbor. Begin lining up at 8:00 PM for the best view. Viewing areas include public spaces Northeast of the Severn River, City Dock, along the Naval Academy Bridge (limited parking area), any of the street end parks facing Spa Creek, and aboard a boat in the Annapolis harbor.