Life Can Be Stressful.

Going on Vacation Doesn’t Have to Be.

At Barefoot Cowboy, our team will help you personalize every part of your dream Caribbean getaway, so you can

spend less time worrying and more time unwinding.

At Barefoot Cowboy, our team will help you personalize every part of your dream Caribbean getaway, so you can spend less time worrying and more time unwinding.

With Barefoot Cowboy, You Can:

Stories From the Path We’ve Traveled Together

Escape on a charter that fits you, your party, and your preferences to a T

Make your vacation as lowkey or action-packed as you want it

Enjoy an itinerary that revolves around what you want to do, not the other way around

Have peace of mind knowing the crew is going above and beyond to keep you safe

Relax in a family-type atmosphere that’s friendly and private

Stop worrying about the little things and start making memories

Why Pay for a Vacation That Isn’t Any Fun?

Many charters, yachts, and cruises offer one-size-fits-all packages that don’t actually fit everyone. As a result, you could find yourself bored, overwhelmed, or stressed out—instead of relaxed and having a blast.

At Barefoot Cowboy, we understand how frustrating it is to spend time and money planning the perfect voyage, only for the real thing to not live up to your expectations. That’s why we let you and up to 9 friends customize every part of your vacation.

As an owner-operated (not crew ran) charter, Barefoot Cowboy ensures every part of your trip is 100% you, from activities to meals to destinations and much more. We’ll help you plan your dream voyage or bring your vision for a once-in-a-lifetime vacation to life, so you can kick off your shoes and truly unwind.

Don’t miss out on the memories of a lifetime. Reach out to Barefoot Cowboy today and embark on a voyage you won’t stop talking about for years to come.

3 Steps to an Unforgettable

and Stress-Free Adventure

01

Reach out to Barefoot Cowboy

Give us a call or send us an email, and we’ll get back to you right away to talk through your ideal getaway and book your trip.

02

Build Your Perfect Vacation

Use our personalization sheet to pick every part of your one-of-a-kind charter voyage, from the destination and activities to meals and drink selection.

03

Experience the Voyage of a Lifetime

Unwind, kick up your feet, and lose yourself in memories you’ll treasure for a lifetime and a vacation you’ll never want to end.

Build Your Dream Caribbean

Escape with Our Charter

Preference Sheet

Do you want to travel to gorgeous destinations? Sample the best local cuisine? Or just lounge on the deck, soaking in the sun?

Download the Barefoot Cowboy Preference Sheet to personalize every aspect of your dream vacation, including:

  • Food, drinks, and restaurants

  • Fun activities based on your activity level

  • How early you want to get up and how late you’ll stay up

  • Special accommodations like diet restrictions or health conditions

  • And much more

You can use this sheet as a guide to plan out any tropical charter getaway. To get your copy, simply fill out the form on this page.

What Other Voyagers Say...

o say this is a once in a lifetime vacation sounds cliche but it's just amazing. The crew, the food, the islands. Everything is top-notch.

Can’t wait to set sail again. This is so much more than a ‘cruise’ could ever offer.

- Jennifer Homer

It was all we dreamed it would be…Food was delicious and beautifully served…The staff exceptional. We’ll go every chance we get!!!

- Barbara Beasley

Beautiful boat with an outstanding crew! They know all of the best spots to visit around the VI, and all of the tips and tricks to make sure you get the most out of your vacation. It’s like having your own local guides as your hosts

- Kyle Rucker