Barefoot Cowboy Yacht Charters

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US Virgin Islands
Charlotte Amalie
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.

26/10/2026

It's diving like you've never experienced before.

Welcome to Wreck Alley, where dozens of vessels have been deliberately sunk to create an artificial reef and an unforgettable scuba diving destination. 🤿🐠

Today, the wrecks are surrounded by marine life, giving divers the chance to explore a unique underwater landscape unlike anything they’ll find on a typical reef dive. Would you take the dive?

25/10/2026

What a busy week Natalie and I have had!! We are back in the islands and Barefoot Cowboy is back in the water after some minor maintenance. She has a some new paint on her bottom and a nice polish from her water line up.

24/10/2026

There’s something magical about the Caribbean after the sun goes down. This beautiful video, captured by one of our guests, shows Saba Rock Resort glowing across the water at night. 🌙⛵️

The sun may be gone, but the island vibes are just getting started.

Cheers to the weekend! 🥂

22/10/2026

You can't think of the Caribbean without thinking of the green sea turtle, and we were lucky to get up close and personal with this fella while snorkeling recently.

Just another reminder that beneath those beautiful blue waters, there’s a whole world waiting to be discovered. 🐢🌊

19/10/2026

If your idea of a perfect Caribbean vacation involves spending as much time in the water as possible, we’ve got a trip for you. 😉

From swimming and snorkeling to paddleboarding, kayaking, scuba diving, fishing, and exploring hidden coves, there are endless ways to experience the Virgin Islands from the water.

With the Barefoot Cowboy, we can build your itinerary around the activities you love most. And that means you get to spend as much time floating in the water as you want!

17/10/2026

Your holiday plans could use a little more Caribbean. 😉🏝️🛥️

There are still openings for December and January aboard the Barefoot Cowboy, and there's no better way to spend the holiday season or start the new year than with your toes in the sand.

Gather your favorite people, leave the winter weather behind, and start the year with days spent swimming, snorkeling, exploring, relaxing, and watching Caribbean sunsets from the water. 🥂🏖️ Book your December or January charter before the remaining dates disappear! https://www.sailingbarefootcowboy.com/contact

15/10/2026

No cookie-cutter itineraries here!

One of the best parts of a private charter is getting to decide what your Caribbean adventure looks like. From the islands you visit to the activities you enjoy, we build the experience around you. 🏝️ Lisa’s 5-star review is a great reminder of why we love what we do: taking the time to create a trip that matches exactly what our guests are looking for.

Tell us what your dream day in the Caribbean looks like, and let’s start designing! https://www.sailingbarefootcowboy.com/contact

12/10/2026

Did you know? 🤔

Charlotte Amalie isn't just the capital of the U.S. Virgin Islands. It's also recognized as the largest historic town in the United States!

From historic buildings and charming streets to its famous harbor, this colorful Caribbean city is packed with stories waiting to be discovered. Plan your trip now: https://www.sailingbarefootcowboy.com/contact

09/10/2026

During one of our snorkeling adventures, we spotted an Atlantic sea nettle jellyfish drifting through the water. 🪼 Beautiful? Absolutely. Something we wanted to get close to? Definitely not! 😂

We kept a respectful distance and enjoyed watching this mesmerizing creature do what it does best: float through the Caribbean blue. The jellyfish here are stunning, in both ways.

06/10/2026

Tacos + Caribbean = a pretty perfect combination. 🌮😋 Whether you're ready to try a little island-inspired taco fusion or you'd rather stick with the flavors you already love, we'll always make a stop for tacos on the Barefoot Cowboy.

Pass the salsa, pour the drinks, and let the good times roll. Happy !

Address

Charlotte Amalie

Website

http://www.sailingbarefootcowboy.com/

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