Water Activities in Annapolis, MD

Sample six rotating craft beers aboard a modern catamaran

Take to the water on a stand-up paddleboard

Celebrate the bride or groom aboard a historic private sailboat

Private floating cantina cruise with DC landmark views and onboard drinks

Cruise or fish aboard a stable 23-foot center console

Cruise the DC waterfront at your own pace—no boating experience required

Paddle Deale’s tidal creeks with a guide who brings local estuaries and history to life

Relax and cruise the South River on a spacious pontoon

A Friday evening creek paddle with live music and a lighted ride back

Make your wellness gathering feel at home on a 45-foot yacht

Raise a glass as you sail into the sunset

Help shape your route through the waterways of Chesapeake Country

Private Chesapeake Bay sailing aboard a 1935 ketch

Share a sunset with the people who matter most

Share a kayak and paddle together

Sail the Miles River aboard a historic 1935 ketch

Take the Helm of a Classic Electric Boat on the Washington Channel

Private evening on the water with sunset views from the South River

Explore Deale's creeks and bay at your own pace on a paddle board

Cruise Chesapeake Bay with your own drinks, music, and flexible stops

Greet the day with a guided paddle at sunrise on Chesapeake Bay

Take the helm for a relaxed cruise along the Annapolis waterfront

Sail a historic ketch at sunset with champagne and Chesapeake Bay views

Paddle the creek, then pause at a local waterfront restaurant for brunch