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Pick Three - Annapolis/Anne Arundel County

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Susan Steckman
Vice President of Communications; Annapolis/Anne Arundel County CVB

What are the three great outdoor adventures you would recommend for groups meeting in Annapolis/Anne Arundel County?


  • Sailing Races: Every Wednesday evening from mid-April through mid-September, groups can participate in the Wednesday Night Sailing Races. About 130 boats compete in the races sponsored by the Annapolis Yacht Club. Several boat classes are featured, including one for two twin 74-foot wooden schooners. The Woodwind and Woodwind II are two 48-passenger boats that groups can board to actually join in the races. The boats also offer two-hour sailing cruises in season. Passengers can help hoist sails, take turns at the helm and enjoy the majesty of 130 wind-filled spinnakers as the sun sets.

  • Boat Charters: Boat charters are also an option. Groups may captain their own power or sailboat with South Rivers boat rentals or charter a boat for cruising with several companies that include Annapolis Sailing Cruises and Watermark Tours, which supplies tour narrators in colonial attire. SJ Koch Duffy Electric Boats offers eco-friendly boats that ply Spa Creek, from which cruisers see views of the Annapolis City Dock, the U.S. Naval Academy and many historic landmarks.

  • Land Tours: Land tours are also popular. Groups may tour the U.S. Naval Academy, the training ground for officers of the U.S. Marine Corps and U.S. Navy. Time the tour to catch the noon formation, when the brigade of 4,000 midshipmen and women assemble Monday through Friday during the academic year. Stops on the tour include the crypt of U.S. naval hero John Paul Jones; the Gallery of Ships at Preble Hall; and Bancroft Hall, the second-largest dormitory in the world. The Four Centuries Walking Tour of Annapolis leads groups through the historic district with guides dressed in colonial attire.