About

Sail Away on a 74-foot, classic-styled wooden schooner. Located in Annapolis, noted as “America’s Sailing Capital”, in the heart of the Chesapeake Bay, Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us on either of our twin schooners, Woodwind or Woodwind II. We offer public cruises up to four times daily, depending on the season. We also offer amazing private events for your family, friends, and co-workers. From interactive team building events where your team sails the boat after fun instruction, or shmooze cruises where you wine and dine them while sailing. Birthdays, reunions, wedding events, & even celebrations of life cruises are also perfect while cruising on the Chesapeake Bay.

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