Get Out on the Water 

A bustling port town in the 18th century, Annapolis is world-renowned as America’s Sailing Capital and one of the top waterfront destinations in the United States. Maryland’s capital city offers countless possibilities for getting out on the water. From 40-minute harbor tours, to two-hour sailing cruises, to daylong excursions, Annapolis is a gateway to North America’s largest estuary, the Chesapeake Bay. 

Annapolis area locals are quick to welcome visiting groups into their sailing culture. There’s always room for more crew members in the famed Wednesday Night Sailing Races that attract more than 130 boats each week from April until September. The Woodwind Schooner and the Woodwind II make it possible for your group to compete in the races. The twin 74’ wooden schooners (one of which appeared in The Wedding Crashers) compete in a class all their own each week. Once aboard a Woodwind, members of your group can help crew or simply relax and enjoy the parade of colorful spinnakers that surrounds them. A host of on-the-water teambuilding possibilities help ensure a fun time for all.  

Annapolis and Anne Arundel County is a Mecca for individuals with a passion for being on or near the water. Our sailing schools, regattas, and weeknight races provide lovers of all things water with a daily fill of waterfront magic. 

If you prefer to keep your feet firmly planted on the ground, grab a seat along the seawall at City Dock – affectionately known as Ego Alley – and watch sail and powerboats strut their stuff for all to see.