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Downtown Sailing Center
- (Baltimore, MD) - Voted as one of the best kept secrets in Baltimore, The DSC is largest and most popular sailing center in the heart of Baltimore. Our non-profit mission is to make sailing affordable and accessible to everyone. We offer high quality sailing programs certified by US SAILING, at very modest prices. We have a fleet of over 40 boats, including J/22's, Sonars, Implulses, Access Dinghies and cruisers. There are numerous recreational sails to help you learn and meet other DSC sailors.
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Footloose Sailing Charters
- (St. Michaels, MD) - Sail with Captain aboard the classic 44 ft. Yacht "Footloose" in St. Michaels in summer & Florida and the Bahamas in winter. The best and oldest charter company in the Bay area, 25 years in business. Berthed at the St. Michaels Harbour Inn and Marina from May to November and Miami, Florida from December to April. 'Come Sail with us'
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Pintail Yachts
- (Stevensville, MD) - Provides the enchantment behind thousands of events in the Chesapeake Bay region – from intimate weddings to lavish corporate parties to spectacular dinner cruising.
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Annapolis Bay Charters, Inc.
- (Annapolis, MD) - Sailing yachts for bareboat charters from annapolis and fishing, corporate parties, weddings and special events for 1 to 250 people. Our reputation serves you well!
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BaySail School & Yacht Charters
- (Havre de Grace, MD) - Simply the best boats on the Bay! Offering a full range of ASA sailing lessons and new and recent model yachts for sailing charters on the Chesapeake Bay in Maryland. BaySail also offers small boat rentals, a Yacht Partnership Program and Club BaySail, our frequent sailor program.
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Schooner Woodwind
- (Annapolis, MD) - The 74-foot twin schooners sail out of Annapolis on regularly scheduled 2 hour tours, corporate charters, private parties, overnight cruises and boat and breakfast.
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Scott Sailmakers Inc.
- (Annapolis, MD) - Custom sails for racing and cruising, repair of existing sails.
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Clipper City, Inc.
- (Baltimore, MD) - The Tall Ship Clipper City. Sailing for public and corporate entertaining. Sails from Baltimore's Inner Harbor Daily.
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South River Boat Rentals
- (Edgewater, MD) - Sailboat and powerboat rentals and charters by the hour, half day, day & overnight and weekly, on the Chesapeake Bay. Unlimited boating club and instructions available.
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Fantasy Sails Inc.
- (Middle River (Baltimore), MD) - Sail the Chesapeake in FANTASY II, a Gemini Catamaran. Sleeps 6 in 3 private staterooms and is fully equipped for cruising. Charter bare-boat or Crewed. Captained excursions are also available (for groups of six or fewer). Mention this website on your initial contact, and receive a 5% discount on your first charter.
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