Cowboy Cruise Company is run by fourth-generation Saltwater Cowboys who have helped care for Chincoteague’s wild pony herd since 1925. Captains Hunter and Ayden grew up on these waters, know every inlet and bloodline, and delight ...
Cowboy Cruise delivers an authentically special experience through their captains, particularly Hunter and Ayden, who bring genuine cowboy credentials to these pony tours. Hunter stands out as a third-generation Saltwater Cowboy and marine biologist whose family has managed these ponies for a century. Reviewers consistently rave about how he knows each pony by name, shares personal stories, and navigates the shallow marshlands in smaller boats to get remarkably close views. The intimate group sizes (just six passengers) create a personalized feel where guides adapt tours to guest interests and answer endless questions. The early morning departures, especially the 8am tours, consistently deliver on the pony guarantee with sightings of multiple herds. Guests regularly spot bonus wildlife including bald eagles, dolphins, herons, and egrets. The company also provides extra touches like blankets for chilly mornings and breakfast during special events like the annual pony swim. Several travelers specifically mention choosing this company after disappointing experiences elsewhere and finding the knowledge, professionalism, and passion far superior. The combination of authentic cowboy heritage, smaller boats accessing unique spots, and genuinely engaging storytelling makes this a standout choice.
We had an AMAZING TIME with Captain Hunter today. Having a Saltwater Cowboy as your guide is so special. Captain Hunter is both a 3rd generation Saltwater Cowboy and a Marine Biologist, making his tours even more unique. His intimate knowledge and personal stories of the ponies were so insightful. With his smaller boat we got to get up closer to the ponies. Since we a small party, he was able to personalize our tour to what we were most interested in seeing. We saw Hildago, Twist and Prince's band, a bald eagle, some great blue heron, egerts and plenty of ibis. Thanks Captain Hunter you are truly the Real Deal!
Tina N.
November 9, 2025
We had an AMAZING TIME with Captain Hunter today. Having a Saltwater Cowboy as your guide is so special. Captain Hunter is both a 3rd generation Saltwater Cowboy and a Marine Biologist, making his tours even more unique. His intimate knowledge and personal stories of the ponies were so insightful. With his smaller boat we got to get up closer to the ponies. Since we a small party, he was able to personalize our tour to what we were most interested in seeing. We saw Hildago, Twist and Prince's band, a bald eagle, some great blue heron, egerts and plenty of ibis. Thanks Captain Hunter you are truly the Real Deal!
Tina N.
November 9, 2025