We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers: Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
You're in Annapolis...get out on the water! There are many great ways to soak up the ambiance, history and general feeling of this historic area; from sailing to cruising, kayaking to chartering.
The easiest way to enjoy the waterways is to hop aboard one of the tour boats. Both Cruises on the Bay™ by Watermark® and the Schooner Woodwind offer public cruises from Downtown Annapolis. If you're looking for a sailing adventure, Woodwind does everything from sunset cruises to special events and lots in between. If you'd like the multi-deck yacht experience, try out the Watermark Day on the Bay cruise to St. Michaels or a quicker 40 minute cruise around the harbor and U.S. Naval Academy.