Best 241 things to do in Annapolis, MD

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

Harbor landmarks, skyline views, and bring-your-own snacks and drinks

Private picnic boat cruise with your food, drinks, and playlist

Sail the Middle River and Chesapeake aboard a private luxury catamaran

Build confidence on the court with personalized coaching for any skill level

Rally, dine, and play through an adults-only group party