Sail the Chesapeake Bay for an afternoon exploring Smith Island
Book a private 2-hour cruise and bring your own food and drinks for a relaxed evening on the water
Canopy-covered river cruising with drinks, snacks, and friends
Private river cruising for your group outing or special event
Gather your crew for a canopy-covered cruise on the Wicomico River
Explore Assateague Island and its coastal wildlife by boat
Tiki-style sunset sailing with Ocean City bay views
Explore Smith Island’s waterman heritage by traditional Chesapeake Bay work boat
Charter the Calico Jack for a private bay cruise with space for up to 32 guests
Join a pirate cruise with buccaneer battles and sunken treasure
Cruise the bay with island beats, sun-and-shade seating, and an onboard bar
Cruise Ocean City’s bays and look for wild ponies near Assateague Island
Start the day on the bay with music, mimosas, and open-water views
Family-friendly tiki boat fun with bay views, music, and sun or shade seating
Bay views, tropical vibes, and a full-service bar to start your Ocean City evening