Annapolis, MD Cruises, Boat Tours & Sailing Charters

Sailing and Boating Excursions Along the Chesapeake Bay

Sailing
Photo © William Sherman/Getty Images

Sailing on the Chesapeake Bay is a special experience and a wonderful way to enjoy visiting  Annapolis, Maryland. Public cruises, boat tours and private charters are available and a fun way to spend time with family and friends while enjoying some of the region's best scenery. You may take a short one or two hour cruise, a half or full day cruise or even a multi-day excursion aboard a variety of sailboats and powerboats. Following is a guide to the companies that offer cruises departing from Annapolis.

Be sure to call ahead to check on availability. Annapolis is located approximately 32 miles from Washington DC and 26 miles from Baltimore’s Inner Harbor. See a map.

Schooner Woodwind Cruises - Departs from the Annapolis Waterfront Hotel. Two 74-foot schooners, the Woodwind and the Woodwind II, are available to cruise the Chesapeake Bay. Two-hour cruises depart daily and longer cruises are scheduled for special events. Private cruises, team-building programs, and student group excursions are available.

The Woodwinds participate every Wednesday night that there is an Annapolis Yacht Club Race. Every October, Woodwind races down the Chesapeake Bay from Annapolis, MD to Portsmouth, VA. The public can participate in many of these events. 80 Compromise Street, Annapolis, MD. (410) 263-8994.

Liberte, The Schooner - Private charters are available in the spring and fall. The Liberte is docked at the Chart House in Eastport. Charters are available for private sailing, corporate events, weddings, bachelorette parties, and cigar party charters.

222 Severn Avenue Annapolis, MD. (410) 263-8234.

Pirate Adventures on the Chesapeake -This cruise is geared towards children and is a great adventure for birthday parties and special occasions. The Sea Gypsy sails from Annapolis several times a day, seven days a week. 311 Third Streeet, Annapolis, MD. (410) 263-0002.

Watermark Cruises - Cruises range from 40-minute to 90-minute, to full day excursions. Specialties include pirate cruises, music cruises and lighthouse cruises. Special event cruises are held throughout the year.

Annapolis City Dock. (410) 268-7601. Watermark operates Annapolis Water Taxi service throughout the Annapolis Harbor including Spa Creek & Back Creek.

Watermen Heritage Tours - Tours give a glimpse of life as a waterman on the Chesapeake Bay, ranging from crabbing adventures to scenic kayak tours, to sunset sails and traditional skipjack charters. 716 Giddings Ave., Annapolis, MD. (443) 261-2369.

Admiral of the Bay -  The tour company operates cruises along the Chesapeake Bay including motor yachts, sailing yachts, fishing charters, weddings and more. Destinations extend from Baltimore to Tilghman Island. (410) 263-5196.

South River Boat Rentals -  Powerboat and sailboat rentals, charters and luxury yacht charters are available in Annapolis, Maryland and the surrounding Chesapeake Bay.  You can rent or charter a boat for the half day, for the day, overnight or weekly. 2802 Solomons Island Road Edgewater, MD (410) 956-9729.