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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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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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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.
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Seanchai Charters
- (Galesville, MD) - Captained sailing charters aboard the 50' ketch SEANCHAI. Enjoy the beauty of the Chesapeake Bay with your own private charter from 3 hours to 7 days. Help sail this classic yacht or just sit back and relax. The choice is yours.
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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.
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