Best 33 things to do in Saint Leonard, MD

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

Soak in Solomons Harbor views with a weather-permitting ride on the Patuxent 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

Sail the Chesapeake on a 1935 ketch with the option to join the crew

Taste six wines on a 2-hour Chesapeake Bay catamaran cruise

Sail the Miles River with room to relax aboard Epiphany

Propose aboard a private yacht with champagne and a harbor sail

Celebrate aboard a private 44-foot catamaran with champagne

Sip six curated wines while sailing St. Michaels’ waterfront

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

Private Chesapeake Bay sailing aboard a 1935 ketch