A chesapeake bay charter offers bareboat yacht sailing charters on the Chesapeake Bay. A chesapeake bay charter offers a carefree sail charter experience for weekend or longer. Sail to Annapolis, St. Michael's, Oxford or other historic towns. Chesapeake Sailing Charters offers the opportunity to sail some of the finest sailboats available on the Chesapeake Bay for charter. Our bareboat charters offer you a sound and beautiful sailboat, some of the most interesting and delightful cruising grounds the U.S. has to offer and terms designed for good value and a carefree chartering experience.
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