Best 22 things to do in Cambridge, MD

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

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

Sail the Miles River aboard a historic 1935 ketch

Plan a private proposal 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

Private Chesapeake Bay sailing aboard a 1935 ketch