Sailing on the Chesapeake

Of course, one of the main attractions of Annapolis is the Bay itself. Short of owning your own boat, there are many ways for visitors to sample the sailing life on the Chesapeake. Many cruises—from as short as 40 minutes to as long as the entire day—leave from the City Dock.

Watermark Cruises is Annapolis's biggest charter and tour service, with many themed tours of varying lengths. Children might especially enjoy Watermark's "Pirates of the Chesapeake" cruise. This "high-seas adventure" is good for short attention spans and is just one hour. Private charters are also available from Watermark. City Dock, Historic District, Annapolis, MD, 21401-1814. 410/268–7601.

Probably the most economical way to get out on the water is on the Water Taxi that runs from Annapolis Harbor to Back Creek. For less than $5 per person you can get out on the water for a short trip. City Dock, Historic District, Annapolis, MD, 21401-1814. 410/263–0033.

For a long trip, consider a Boat & Breakfast on the Schooner Woodwind. Take a two-hour sail and then spend the night dockside in double-berth staterooms. 80 Compromise St. at the Annapolis Marriot Waterfront Hotel, Annapolis, MD, 21401-1810. 410/263–7837.

A comprehensive listing of all of the sailing possibilities is available on the Visitors Bureau Web site

There are no results

Previous Experience

Top Reasons to Go to Annapolis and Southern Maryland

All Top Experiences


Book A Trip



  • CARS

Trip Finder