Free Concierge Service
    Text or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Concierge Support

    • Help Center
    [email protected](650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Cowboy Cruise Company

    Cowboy Cruise Company

    5.0 • 112 reviews
    Chincoteague, VA

    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 ...

    Report an issue

    Book Cowboy Cruise Company

    Addon image

    Chincoteague Island Pony & Shellfishing Cruise

    Cruise Chincoteague and harvest clams and oysters along the way

    From$132person
    Addon image

    See Wild Chincoteague Ponies on a Guided Tour

    Cruise to Chincoteague pony grazing pastures with a 50% refund if you don’t spot ponies

    From$79person
    Addon image

    Wild Chincoteague Pony Guided Boat Tour

    Cruise to see wild Chincoteague ponies with a Saltwater Cowboy guide

    From$74person
    Addon image

    Sunset Boat Cruise in Chincoteague Island

    Private 1.5-hour sunset cruise around Chincoteague Island for up to 6

    $381.60
    Addon image

    Dig Clams & Shuck Oysters on a Chincoteague Tour

    Dig clams, pull oyster cages, and learn to shuck on an interactive aquafarm tour

    From$79person
    Addon image

    Early Bird Spring Foal Boat Tour

    Find newborn foals and see as many pony herds as possible with a Saltwater Cowboy captain

    From$90person

    Review summary

    5.0
    Excellent
    114 reviews•Google Maps

    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.

    What people are saying

    Review 1 of 5
    5/5

    Excellent tour, small boat = close to ponies. The guide knew every point by name. Most knowledgeable tour guide ever. Guide not concerned about the time as much as he was making sure we saw lots of ponies and horses. Our tour was excellent, we saw one foal being born and another take their first steps!!! This tour company is the best.

    Photo of Shawn Wilson

    Shawn Wilson

    May 12, 2026

    Review 1 of 1
    5/5

    Excellent tour, small boat = close to ponies. The guide knew every point by name. Most knowledgeable tour guide ever. Guide not concerned about the time as much as he was making sure we saw lots of ponies and horses. Our tour was excellent, we saw one foal being born and another take their first steps!!! This tour company is the best.

    Photo of Shawn Wilson

    Shawn Wilson

    May 12, 2026