Explore Photos of Previous Charter Adventures

See how friends and families let loose, kick back, and soak up the sun on their Barefoot Cowboy vacations. Browse photos of past Caribbean excursions below!

Explore Photos of Previous Charter Adventures

See how friends and families let loose, kick back, and soak up the sun on their Barefoot Cowboy vacations. Browse photos of past Caribbean excursions below!

Highlights from Recent Charter Trips

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Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway Norway
Norway Norway Norway Norway Norway Norway Norway Norway Norway

"Fantastic trip with Barefoot Cowboy Charters!"



"First, the boat is beautiful and the beds and linens are really nice! There is an extra large seating area on the second level of the boat where we spent a lot of our time when moving from island to island which is super nice and includes a sink, ice maker, and bar!



The main level has a nice seating area inside as well as a large table outside on the patio! Finally, Captain Roy and Natalie were the perfect hosts! From breakfast & coffee in the mornings to cocktails throughout the day and the beautifully set table and wonderful dinners in the evening, we were completely spoiled!



I would definitely recommend The Barefoot Cowboy Charter to anyone looking for a luxury adventure in the BVIs!"



-Nicki Crump

"Five stars!"



“If you think you’d enjoy a week of adventure, excitement, marine beauty, action, the fascination of sailing on a medium-sized vessel on the Caribbean seas and have a tight group of travel friends who share these passions with you, this is the experience for you!



Great food and drink on the boat, and daily opportunities to visit fun pubs, bars, and restaurants along the way with breathtaking landscapes 24/7. It’ll be a memory you’ll never forget.”



-Walter Riggs

What Memories Will You Make on Your Island Getaway?

Reach out using the button below or by calling to plan your one-of-a-kind charter vacation now. Whether you aren’t sure how to get started or you have dreamed up every detail, we’ll work together to ensure your trip fits your party perfectly.

What Memories Will You Make on Your Island Getaway?

Reach out using the button below or by calling to plan your one-of-a-kind charter vacation now. Whether you aren’t sure how to get started or you have dreamed up every detail, we’ll work together to ensure your trip fits your party perfectly.

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