Water Activities in Grasonville, MD

Sail a Historic 1935 Ketch on the Miles River

Sail the Middle River and Chesapeake aboard a private luxury catamaran

Cruise Chesapeake Bay waterways with fall views and complimentary warm apple cider

Cruise Chesapeake Bay aboard a 60-foot Viking with captain, crew and fuel included

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

Rent two boats at once and receive a 10% discount

Take the controls for a Chesapeake Bay jet ski ride

Sail the Miles River with room to relax aboard Epiphany

Cruise the South River with spacious seating, storage, and an onboard toilet

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

Cruise quietly with your own food, drinks, and music

Bring your own drinks and cruise Annapolis on a private tiki boat for 8–16

Celebrate aboard a private 44-foot catamaran with champagne

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

Sail Chesapeake Bay at sunset with champagne and light bites

Cruise the South River with 250 HP power and an onboard toilet

Take a versatile 19-foot boat out for watersports, dining stops, and easy cruising

Build paddleboarding skills with certified coaches, then paddle at your own pace

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

Cruise quietly with your own food, drinks, and music

Sample six rotating craft beers aboard a modern catamaran

Cruise or fish aboard a stable 23-foot center console

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

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