Sail a Historic 1935 Ketch on the Miles River
Discover the shoreline stories behind St. Michaels
Paddle Dorchester County waterways with equipment delivered to your location
Private bay fishing with gear, bait, and fish filleting included
Step inside a surviving Bucktown store tied to Harriet Tubman's early life
Explore Maryland's Eastern Shore aboard a 1942 training aircraft
Explore St. Michaels after dark through ghost stories and maritime history
Step inside one of Dorchester County's five intact Georgian historic homes
Take a quiet pause with a different soundscape each week
Sample Six Curated Wines While Sailing Chesapeake Bay
Sail the Miles River with room to relax aboard Epiphany
Pair sunset views with your own music and drinks
Celebrate on the water with your own drinks, music, and company
See Maryland's Eastern Shore from between the wings of a vintage biplane
Walk Easton's haunted past through its notorious Tragedy Triangle
See the Eastern Shore from an open cockpit, with room to customize your route
Build paddleboarding skills with certified coaches, then paddle at your own pace
Paddle Deale’s tidal creeks with a guide who brings local estuaries and history to life
Take to the water on a stand-up paddleboard
Propose aboard a private yacht with champagne and a harbor sail
Celebrate aboard a private 44-foot catamaran with champagne