Discover ChincoteagueIsland's Wild Side
Wild pony tours, nature boat excursions, and guided hunts with Captain Randy — a lifelong island native and your expert guide.
Your Island Adventure Awaits
All tours and events run 1½–2 hours unless otherwise noted.
Nature Tours
Wild pony tours and nature boat excursions through the back bays of Chincoteague. Sunrise, sunset, and Wild Pony Expedition tours with Captain Randy.
Pony Swim & Events
Witness the world-famous Chincoteague Pony Swim from the water, plus on-request rocket launches, fireworks, and photography charters.
Guided Hunting
Schedule a guided waterfowl hunt in the waters surrounding Chincoteague and Assateague Island with Captain Randy.
Captain Randy
“Every trip on the water is different. The ponies, the dolphins, the sunsets — I've been doing this for decades and it still takes my breath away. There's nothing like sharing this island with folks who love it as much as I do.”
A lifelong Chincoteague Island native, Captain Randy has spent decades on these waters. His deep knowledge of the island's ecology, history, and wildlife ensures every tour is an unforgettable experience.
“Come as a guest, leave as a friend.”
What Our Guests Say
“Captain Randy was amazing! He knew exactly where to find the ponies and dolphins. The sunset tour was the highlight of our entire trip.”
Sarah M.
TripAdvisor
“We've done this tour three years in a row now. Captain Randy's knowledge of the island and its wildlife is unmatched. Highly recommend!”
Mike & Linda T.
TripAdvisor
“The kids were thrilled to see the wild ponies so close. Captain Randy made it educational and fun. Will definitely be back!”
Jennifer K.
TripAdvisor
Ready for Your Adventure?
Book your Chincoteague Island tour today and experience the beauty of Virginia's Eastern Shore with Captain Randy.