Help shape your route through the waterways of Chesapeake Country
Learn to glide above the water with step-by-step instruction
Celebrate on the water with your own drinks, music, and company
Sip six curated wines while sailing St. Michaels’ waterfront
Paddle Deale’s tidal creeks with a guide who brings local estuaries and history to life
Share a sunset with the people who matter most
Break a sweat in a color-lit rage room with your crew
Sail Chesapeake Bay at sunset with champagne and light bites
Private evening on the water with sunset views from the South River
A Friday evening creek paddle with live music and a lighted ride back
Enjoy a relaxed start to the day with a boat all to yourselves
Discover the shoreline stories behind St. Michaels
Sample six rotating craft beers aboard a modern catamaran
Explore Deale's creeks and bay at your own pace on a paddle board
Bring your own drinks and cruise Annapolis on a private tiki boat for 8–16
Cruise Chesapeake Bay with your own drinks, music, and flexible stops
Celebrate the bride or groom aboard a historic private sailboat
A relaxed captain-led ride through Chesapeake Bay tributaries to Annapolis
Cruise Chesapeake Bay coves and historic waterfronts en route to Galesville
Greet the day with a guided paddle at sunrise on Chesapeake Bay