TOP 30 Sailboat charters in Annapolis, Maryland

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Island Chill Yacht Charters (ICYC) is a travel agency located at 1444 Shore Drive in Edgewater, Maryland, United States. We specialize in creating the 'Relaxing Excitement of the Islands' on private sail and powerboat cruises for families, friends, and couples. Conveniently situated in historic Londontowne, we are close to Washington D.C. and Baltimore, just 6 miles south of Annapolis - the 'Sailing Capital of America!' Our cruises are perfect for hot summer days and chill sunsets, making them ideal for birthdays, anniversaries, bachelorette parties, corporate retreats, national holidays, and special events. Choose from our 43-foot sailboat (Therapy), 34-foot powerboat (Irie Vibes), or 20-foot bow-rider powerboat (Tallawah) for captained cruises along the South and Rhode Rivers, Chesapeake Bay, and Thomas Point Shoal Lighthouse. Enjoy swimming, paddle boarding, floating lily pads, sunbathing, beaches, sandbars, islands, kayaking, and fishing options.

The Annapolis Yacht Club is a prestigious and historic institution located at 2 Compromise Street in Annapolis, Maryland. With a rich maritime tradition dating back to its founding in 1886, the club offers members and guests a wide range of amenities and activities, including sailing races, social events, dining options, and access to a beautiful waterfront setting. Boasting a welcoming and inclusive atmosphere, the Annapolis Yacht Club is a cherished destination for boating enthusiasts and community members alike.

Schooner Woodwind Offsite Business Office is a travel agency located at 1930 Lincoln Drive in Annapolis, Maryland. Our office is dedicated to providing exceptional service and assistance to our clients in planning their travel adventures on the Schooner Woodwind sailboats. Whether you are looking to book a private charter, a team building event, or a unique corporate outing, our experienced team is here to help create a memorable and enjoyable experience for you and your group. Contact us today to start planning your next sailing adventure on the beautiful waters of Annapolis.

Granmar Sailing is a premier travel agency located at #8 Randall Street in Annapolis, Maryland, United States. Specializing in sailing adventures, Granmar Sailing offers a variety of packages for individuals and groups looking to explore the open waters. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Granmar Sailing has something for everyone. With experienced captains and top-of-the-line equipment, you can trust that your sailing experience with Granmar Sailing will be safe, enjoyable, and unforgettable. Book your next sailing adventure with Granmar Sailing and set sail for an experience of a lifetime.

Chronic Sailing is a premier sailing school located at 7082 Bembe Beach Road in Annapolis, Maryland, United States. Our institution offers top-notch sailing instruction for all skill levels, from beginners to advanced sailors. Whether you're looking to learn the basics of sailing or improve your racing techniques, our experienced instructors are here to help you achieve your goals on the water. Join us at Chronic Sailing and experience the thrill of sailing in one of the most beautiful locations on the East Coast.

Chesapeake Boating Club, located at 213 Eastern Avenue in Annapolis, Maryland, is a unique institution that offers sail and power boat charters and rentals. Founded in 1992 in the Historic Eastport section of Annapolis, the club prides itself on providing flexible, fun, and affordable boating experiences. With a variety of boats ranging from 17' to 36' in length, members can choose the right vessel for any adventure on the Chesapeake Bay. In addition to boat rentals, the Chesapeake Boating Club also offers instruction in sailing and powerboating. The club's experienced J World coaches provide online educational seminars during the off-season to help members enhance their boating skills.

Knapp’s Narrows Marina & Inn is a waterfront lodging institution located on Maryland’s Eastern Shore in Tilghman Island. With a full-service boatyard, 1000-foot floating dock, swimming pool, and 20-room waterfront inn, guests can enjoy stunning views of the Chesapeake Bay from their own balcony or patio. The marina also offers lighthouse tours, fishing charters, and a taste of Chesapeake culture and history in the town of Tilghman. Environmentalists and bird watchers will appreciate the wildlife and expansive views, including sightings of Eagles, egrets, herons, and Monarch butterflies. Sunset sailboat cruises, lighthouse tours, and professional fishing charters are also available for guests to enjoy. Knapp’s Narrows Marina & Inn is the perfect destination for special events, family reunions, conferences, and more. Conveniently located within a day trip from Annapolis, St. Michael's, and other nearby cities, it is the ideal getaway for those looking to experience the beauty of the Chesapeake Bay.