Water Activities in Annapolis, MD

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

Private catamaran sailing with harbor views and Miles River breezes

Private cruising with your playlist, swim stops, and bring-your-own drinks

Sail the Miles River aboard a spacious catamaran

Harbor views and wind-powered sailing on the Miles River

Savor rotating craft beer tastings aboard the historic Lady Patty

Build Practical Sailing Skills With Private, Hands-On Instruction

Take the Helm and Learn Hands-On Sailing Skills

Make your vows your own aboard a private Chesapeake Bay catamaran

Exchange vows aboard a historic sailboat with a ceremony shaped around you

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

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

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

Sail the Middle River and Chesapeake aboard a private luxury catamaran

Cruise Kent Narrows waterways with local narration and panoramic views

Build paddling confidence on a guided harbor passage with a relaxing shuttle return

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.

Set your own soundtrack for a private outing on the Potomac

Cruise the Potomac in a private cabin boat for up to 6 guests

Leave the cruising to your captain and relax on the water