Best 74 things to do in St Michaels, MD

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

Cruise Chesapeake Bay to Rock Hall with time to explore ashore

Cruise the Chesapeake Bay to explore historic St. Michaels by boat

See Chesapeake landmarks and explore historic Oxford by boat

Customize a shaded private outing on the Upper Choptank River

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

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

Pedal through the countryside for a winery tour and tasting

Paddle brackish waterways with a guide and look for local wildlife

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

Pedal flat scenic roads and watch for birds and wildlife

Paddle a brackish river beside Blackwater Refuge

Paddle a brackish waterway beside Blackwater Refuge

Paddle the Little Blackwater River and watch for wildlife along its banks

Pedal refuge and marsh roads with a bike, helmet, and map

Step inside a surviving Bucktown store tied to Harriet Tubman's early life

Paddle Dorchester County waterways with equipment delivered to your location

Bottom-fish with room to cast on a 16-angler boat

Private bay fishing with gear, bait, and fish filleting included

Celebrate your occasion aboard a private party boat on Chesapeake Bay

Paddle Bear Creek’s calm waters and watch for local wildlife