Annapolis Things to Do on the Water

Call of the Chesapeake

If your idea of a great vacation is getting on the water, you've come to the right place. Annapolis is the gateway to North America's largest estuary, the Chesapeake Bay, and we're willing to share!

Since its founding as Anne Arundel Town in 1649, Annapolis’s heritage has been linked to the water. Yesterday’s bustling port city is today’s boater’s paradise. Annapolis offers countless ways to get out on the water – from 40-minute to daylong public cruises, to charters, to boat and breakfasts. Our sailing races and regattas are world class. But don’t take our word for it, don your Docksider’s and head to City Dock for an education in all things nautical.

Watch boaters strut their stuff along Ego Alley. Family in tow? Defend your kids as they battle pirates aboard the Sea Gypsy. How about renting a canoe, kayak, paddle board, or peddle boat? Our 400 miles of coastline are yours to explore. Relaxation on your mind? Stake out a seat at your favorite waterfront restaurant and watch the parade go by. The perfect solution to whatever ails you? Just add water!

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On the Water News & Stories

Apr 1, 2013

Spring Boating Sails into Port

Spring is here! In Annapolis and the Chesapeake Bay that means boats are coming out of hibernation and are once again gracing the Annapolis Harbor and Chesapeake Bay. It won’t be long before a host of boats resume their favorite moorings at Ego Alley and lovers of all things nautical flock to City Dock to join in the boating action...more

Jan 1, 2013

Winter Sailing, Anyone?

You might think all of our boats are shrink wrapped and safely tucked away for the winter months. But in a destination with water for a middle name, it's hard to put the sails away - no matter what the weather might be. So, if you need a sailing fix in the height of winter.....more