things to do in Chesapeake Beach, MD

Build your confidence above the water with step-by-step coaching

Go top-down in a vibrant yellow sports car

Share time on the water with friends or family

Share a Bentley pontoon outing with friends or family

Glide across the water on a stable stand-up paddleboard for a flexible 1- or 2-hour session

Build advanced sailing skills in a 5-day Flying Scot course for ages 8–15

Build practical sailing skills with hands-on Flying Scot instruction

Cruise the Patuxent River for fishing, swimming and water sports

Cruise with family and friends on a stable pontoon built for sightseeing and tubing

Cruise the Patuxent River at your own pace by pontoon

Paddle Deale’s quiet creeks and bays at your own pace

Explore Deale's creeks, estuaries, and bay by kayak

Let pedal power put your creativity in motion

Rent a double kayak on the Anacostia River from James Creek Marina

Relax on the water while an included captain and crew handle the cruising

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

Step inside one of Dorchester County's five intact Georgian historic homes

Explore Chesapeake Country on a private cruise shaped around your interests

Take in maritime history and waterfront scenery from your own private boat

Help shape your route through the waterways of Chesapeake Country

Share a sunset with the people who matter most

Enjoy a relaxed start to the day with a boat all to yourselves

Feel the energy of live football alongside passionate Commanders fans

Paddle the Anacostia River from Ballpark Boathouse