things to do in Saint Michaels, MD

Celebrate aboard a private 44-foot catamaran with champagne

Paddle brackish waterways with a guide and look for local wildlife

Sip six curated wines while sailing St. Michaels’ waterfront

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

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

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

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

Sail Chesapeake Bay at sunset with champagne and light bites

Sample six rotating craft beers aboard a modern catamaran

Pedal flat scenic roads and watch for birds and wildlife

Celebrate the bride or groom aboard a historic private sailboat

Paddle a brackish river beside Blackwater Refuge

Paddle a brackish waterway beside Blackwater Refuge

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

A relaxed captain-led ride through Chesapeake Bay tributaries to Annapolis

Cruise Chesapeake Bay coves and historic waterfronts en route to Galesville

Explore Deale's creeks and bay at your own pace on a paddle board

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

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

Sail the Miles River aboard a historic 1935 ketch