Water Activities in Saint Michaels, MD

Sail a Historic 1935 Ketch on the Miles River

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

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

Take the controls for a Chesapeake Bay jet ski ride

Sail the Miles River with room to relax aboard Epiphany

Paddle the Chicamacomico River, then tour the winery and taste wine

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

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

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

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

Celebrate aboard a private 44-foot catamaran with champagne

Paddle brackish waterways with a guide and look for local wildlife

Sail Chesapeake Bay at sunset with champagne and light bites

Paddle a winding one-way river route with a shuttle back to your vehicle

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

Sample six rotating craft beers aboard a modern catamaran

Paddle a brackish river beside Blackwater Refuge

Cruise or fish aboard a stable 23-foot center console

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

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