Best 69 things to do in Chincoteague, VA

Private river cruising for your group outing or special event

Explore Smith Island’s waterman heritage by traditional Chesapeake Bay work boat

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

Uncover Berlin's haunted legends after dark

Taste Berlin, MD on a guided Main Street walk with 5–6 tasting stops

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

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

Bring your drinks for an after-sunset barge party with music and lights

Explore island waterways, pony habitat, and local history from the water

Hear Snow Hill’s haunted history along the dark waters of the Pocomoke River

Cruise to Smith Island and enjoy a crab feast with island flavors