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Maryland Directory for Sailing
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Maryland Sailing

  • AAA Sail to St. Michaels - (Kent Narrows, MD) - Enjoy a sailboat charter to fun and discovery while sailing into St. Michaels from Kent Narrows. Visit the Chesapeake Bay Maritime Museum, the town's shoppes and restaurants. Hoist the sails, take the helm, or just sit back, relax, and listen to the tales of a Chesapeake Bay sailboat Captain. This is a great day to enjoy Maryland's great waters, wildlife, and shore lines.
  • 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.
  • 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'
  • 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.
  • Scott Sailmakers Inc. - (Annapolis, MD) - Custom sails for racing and cruising, repair of existing sails.
  • Selina II Sailing Charters - (St Michaels, MD) - "Selina II" Historic Sailing Charters - The historic 1926 catboat Selina II offers 2 hour sails daily from the St Michaels Harbour Inn & Marina departing at 10am, 12:30pm, 3pm and their sunset champagne cruise operates from 5:30-7:30PM. Private half day, full day, and overnight excursions are also available for those wanting to spend more time on the water. The Selina II limits her passengers to just 6 guests for an intimate taste of the history of sail.
  • HarborSail LLC - (Baltimore, MD) - Providing sailboat harbor tours, sunset cruises, rentals, charters and instruction. Boats depart from Fells Point. Enjoy a day or sunset cruise on Catawampus II a 41' Hunter. Our guests are welcome to sit back and enjoy the historic sites or participate by hoisting a sail. HarborSail limits her voyage to six passengers.
  • 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.
  • Sailtime Baltimore - (Baltimore, MD) - The newest way for Maryland sailing on the Chesapeake Bay. You get access to a new Hunter yacht. Whether you want to sail for a half day,full day,weekend or a full week. SailTime Membership is the least expensive way to get sailing on the Chesapeake Bay. Dont buy a used boat. Join where you can sail a brand new yacht with no marina fees, bank payments, maintenance costs, or insurance fees. Enjoy luxury sailing in Baltimore for less money & zero worries. If you have no experience, we have certified instructors to get you under way.
  • 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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