Sail the Chesapeake Bay for an afternoon exploring Smith Island
Take the helm of a 20-foot pontoon for a self-guided outing
Paddle calm back bays with route guidance for the day
Overnight bike options for an independent Assateague ride
Choose a kayak, paddleboard, or canoe for time on the water
See the Pony Swim from a comfortable pontoon boat
Escape the crowds with flexible rides to a secluded Assateague beach
Explore Chincoteague waters with fishing licenses and fuel included
Watch dawn light the marshes and waterways around Chincoteague and Assateague
Ride a guided jet ski eco tour around Chincoteague and Assateague
Cruise Chincoteague Bay at golden hour on a private luxury pontoon
Take the helm for a sunset cruise across Chincoteague Bay
Sunset views, two decks, and a waterslide for your private bay outing
A private on-water view of the annual Chincoteague Pony Swim
Find newborn foals and see as many pony herds as possible with a Saltwater Cowboy captain
Cruise to see wild Chincoteague ponies with a Saltwater Cowboy guide
Private 1.5-hour sunset cruise around Chincoteague Island for up to 6
Cruise Chincoteague waters for lighthouse views and possible wild pony sightings
Hear Snow Hill’s haunted history along the dark waters of the Pocomoke River
Pick up a bike at the Visitor Center and ride for 2 hours