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Maryland Sports and Recreation/Sailing

  • Maritime Charters - (Baltimore, MD) - Sail the Chesapeake Bay with Maritime Charters aboard the classic wooden boat, the Howard Blackburn
  • Blue Crab Chesapeake Charters - (Rock Hall, MD) - Daysails and sunset cruises leaving up to three times daily from Watermans Crab House in Rock Hall. All cruises are an hour and a half and cost just $25.00 per person. Please check the website for details.
  • Lady Patty Sail Charters - (Tilghman Island, MD) - Sails daily from Knapp's Narrows Marina into the waters of the Chesapeake Bay. Experience the bronze and teak beauty of this 45' classic Bay Ketch. Reservations suggested.
  • 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'
  • 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.
  • 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!
  • 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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Maryland Sailing

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