Barefoot Cowboy Yacht Charters

Barefoot Cowboy Yacht Charters Barefoot Cowboy Yacht Charters is a 58' Leopard Sailing Catamaran serving the Virgin Islands. We offer crewed charter vacations for up to 10 people.

Guests like these make everything worth it. 🫶 Thank you so much for the kind words!
11/06/2026

Guests like these make everything worth it. 🫶 Thank you so much for the kind words!

Left? That's right. ⬅️🚗 The U.S. Virgin Islands is the ONLY place in the U.S. where people drive on the left side of the...
09/06/2026

Left? That's right. ⬅️🚗 The U.S. Virgin Islands is the ONLY place in the U.S. where people drive on the left side of the road. (But the cars have steering wheels on the left, too!)

We don't need an excuse to hit the trails, but National Trails Day makes a good one! Where are you hiking next? 🌵🏞️
07/06/2026

We don't need an excuse to hit the trails, but National Trails Day makes a good one! Where are you hiking next? 🌵🏞️

Looking for local island flavor? Hendo's Hideout is one of our go-to stops. 🏖️ Located on the soft sandy beach of White ...
04/06/2026

Looking for local island flavor? Hendo's Hideout is one of our go-to stops. 🏖️ Located on the soft sandy beach of White Bay, Hendo's is a great place to pick up a cocktail, indulge in fresh seafood, or get a taste of Caribbean cuisine.

Plan your trip now: sailingbarefootcowboy.com/contact

Considering how much wildlife depends on it, the reef deserves a little respect! ✨🪸🐠 Show your love by only wearing reef...
01/06/2026

Considering how much wildlife depends on it, the reef deserves a little respect! ✨🪸🐠 Show your love by only wearing reef-safe sunscreen.

Sunscreen with mineral ingredients (zinc oxide or titanium dioxide) protects skin without harming coral reefs, so we can all enjoy the beauty of the oceans for years to come.

This week’s stop: Cow Wreck Beach Bar on Anegada, where the views are unreal and the conch fritters are even better. 🐚😎
28/05/2026

This week’s stop: Cow Wreck Beach Bar on Anegada, where the views are unreal and the conch fritters are even better. 🐚😎

Here's a tip: Bring some cash while you're traveling in the Virgin Islands. Bars, taxis, and restaurants all appreciate ...
26/05/2026

Here's a tip: Bring some cash while you're traveling in the Virgin Islands. Bars, taxis, and restaurants all appreciate tips! 💵🫶

Credit cards are good for other purchases (with the exception of American Express because some places won't accept it).

Celebrating National Turtle Day with one of Roy Pat’s incredible underwater sightings. 🤿🐢 Isn't she a beauty?
23/05/2026

Celebrating National Turtle Day with one of Roy Pat’s incredible underwater sightings. 🤿🐢 Isn't she a beauty?

Happy National Rescue Dog Day 🐾💛 Rescue dogs have a way of changing your life. And while Pirate Pete may not be a rescue...
20/05/2026

Happy National Rescue Dog Day 🐾💛 Rescue dogs have a way of changing your life. And while Pirate Pete may not be a rescue, we’re pretty sure he rescued us. 🐶

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Charlotte Amalie

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