Best results for Water Activities in Chesapeake Beach, MD

Take the controls for a Chesapeake Bay jet ski ride

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

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

Sail a Historic 1935 Ketch on the Miles River

Sail the Miles River with room to relax aboard Epiphany

Celebrate aboard a private 44-foot catamaran with champagne

Sail Chesapeake Bay at sunset with champagne and light bites

Sample six rotating craft beers aboard a modern catamaran

Celebrate the bride or groom aboard a historic private sailboat

Sail the Miles River aboard a historic 1935 ketch

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

Private catamaran sailing with harbor views and Miles River breezes

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

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

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

Cruise or fish aboard a stable 23-foot center console

Relax and cruise the South River on a spacious pontoon

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

Cruise Chesapeake waterways to Annapolis landmarks with a captain

Cruise Chesapeake Bay coves and historic waterfronts en route to Galesville