Annapolis Sailing Cruises is a family-owned business located in the heart of the Chesapeake Bay, offering unforgettable sailing experiences in Annapolis, Maryland. With their two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, guests can embark on a true sailing adventure, sailing from the historic Annapolis waterfront, past the Naval Academy, and into the Chesapeake Bay. Whether you want to help raise the sails, steer the boat, or simply relax and enjoy the beauty of Annapolis and the bay, Annapolis Sailing Cruises provides engaging and enthusiastic captains and crew to make your sailing experience a memorable one.
With a carefully crafted menu of food and drink, Annapolis Sailing Cruises specializes in specialty sailing cruises that make any day exceptional. From private cruises for social events or corporate outings to public sailing cruises and special events, guests can celebrate on the Chesapeake while taking in the stunning views and enjoying the company of their loved ones. As a top-rated sailing tour company in Annapolis, Annapolis Sailing Cruises is known for their professionalism, personable crew, and their commitment to providing an unforgettable sailing experience for all.
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