Water Activities in Chesapeake Beach, MD

Take the helm for a relaxed cruise along the Annapolis waterfront

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

Build Practical Sailing Skills With Private, Hands-On Instruction

Make your vows your own aboard a private Chesapeake Bay catamaran

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

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

Sail a Historic 1935 Ketch on the Miles River

Enjoy flexible 2–4 hour outings on a nimble two-person boat

Paddle the Anacostia River with a single kayak rental

Paddle the calm Washington Channel with easy sit-on-top doubles and flexible 1–4 hour rentals.

Paddle the Washington Channel with a single kayak rental at the Wharf

Soak in a private hot tub while cruising past DC monuments and skyline

Paddle with a guide, then explore Blackwater by bike at your own pace

Sail past iconic monuments on a lively tiki boat with onboard bar and music.

Bottom-fish with room to cast on a 16-angler boat

Paddle from Eastport or take a sit-inside kayak to your favorite spot

Chesapeake water views with a laid-back island vibe

Cruise the DC Waterfront with premium onboard entertainment and bow seating

Celebrate the bride or groom aboard a historic private sailboat

Cruise Kent Narrows waterways with local narration and panoramic views

Take the controls for a Chesapeake Bay jet ski ride

Cruise the Potomac with your own food, drinks, and music on an 18-foot picnic boat.

Bring your own food and drinks for a relaxed private cruise with music and river views

Set your own soundtrack for a private outing on the Potomac