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Maryland School of Sailing & Seamanship
- (Rock Hall, MD) - The Maryland School offers basic to advanced sail training cruises, and is unique in their ability to bring students from the beginner sailing level to their dream of advanced ocean cruising. Beginning live-aboard cruises are offered in the Chesapeake Bay and the Virgin Islands aboard Island Packet cruising sized yachts. Advanced training cruises have destinations such as Bermuda, Bahamas, Virgin Islands, Florida, New England, and Canadian Gulf Islands. ASA certifications from 101 through 108 offered.
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Haven Charters
- (Rock Hall, MD) - Bareboat sailing charter rentals on the Chesapeake Bay. 30 to 45 foot sailboats for charter. Easy daysails to Annapolis, St. Michaels and Baltimore. Sailing instruction available by USCG certified captains. Keelboat certification offered.
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BaySail School & Yacht Charters
- (Havre de Grace, MD) - Simply the best boats on the bay. BaySail offers new and recent model sailing yachts for charter either bareboat, captained or instructional. Smaller daysailers are also available for rent. In addition, BaySail offers a full range of sailing courses from beginner through bareboat certification all of which are certified by the American Sailing Association. We're located on the Chesapeake Bay only an hour from Philadelphia and 45 minutes from Baltimore.
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Annapolis Sailing School
- (Annapolis, MD) - America's oldest and largest sailing school. Learn from the best. Children's and adult programs 2 to 5 days.
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Chesapeake Sailing School
- (Annapolis, MD) - Since 1980, CSS has offered Basic through Advanced sailing lessons for adults and families. National certification is available as well as private and custom courses on monohulls and catamarans.
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Getaway Sailing
- (Baltimore, MD) - Providing adult instruction, kids summer camps, corporate sailing events, clubs, charter/rental, Baltimore harbor cruises, Chesapeake Bay cruises, international cruises, senior citizens club, racing, sailing Baltimore, and sailing Chesapeake Bay.
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Upper Bay Sailing School
- (Worton, MD) - ASA Certified Sailing Instruction Beginner to Advanced Coastal Cruising. Two locations - Worton Creek in the Summer and Tortola, British Virgin Islands in the Winter. Instructor of the Year Award. Also an ASA Gold star rated school. Live-aboard classes taught on Beneteau sailing boats 30 to 42 ft long. Boats for charter also.
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Ocean Sailing Academy
- (Annapolis, MD) - Provides all US Sailing certifications from Basic Keelboat through Ocean Passage Making at the school's Annapolis location. With the school's location on Back Creek, easy access to open water means all course time for all courses is spent on the vessel and on the water. Ocean Sailing Academy: Serious Instruction for Serious Sailors.
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