Best 61 things to do in Grasonville, MD

Cruise Kent Narrows waterways with local narration and panoramic views

Toast the evening on a Chesapeake Bay cruise with an onboard full bar

Explore St. Michaels after dark through ghost stories and maritime history

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

Sail a Historic 1935 Ketch on the Miles River

Sample Six Curated Wines While Sailing Chesapeake Bay

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

Discover Annapolis's Navy culture, history, and Chesapeake character

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