The Barefoot Cowboy Experience

From unforgettable destinations to squeaky clean cabins, Barefoot Cowboy vacations are unlike any other. Browse our favorite destinations, excursions, restaurants and more below!

The Barefoot Cowboy Experience

From unforgettable destinations to squeaky clean cabins, Barefoot Cowboy vacations are unlike any other. Browse our favorite destinations, excursions, restaurants and more below!

Gallery

Make Memories, Not Regrets

Planning a trip to the Caribbean can be stressful. From choosing your island destinations to hand-picking the right excursions, it's easy to get overwhelmed. Our team helps you enjoy a worry-free, regret-free vacation experience without having to do it all on your own.

With Barefoot Cowboy, you can explore luxury Caribbean islands and hidden gems on a cozy charter with up to 10 guests. We have a wide selection of activities and excursions for every type of traveler in your party—whether you’re thrill seekers or beach bums!

Our customization options include:

  • Departure and arrival times

  • Destinations

  • Cuisine and drinks

  • Activities

  • Itinerary schedule

Scroll down to explore some of your trip options. You can personalize as much as you like. If you aren’t sure how to make the most of your Caribbean getaway, our team can provide suggestions of our go-to stops (it’s one of our favorite parts of the job!).

Make Memories, Not Regrets

Planning a trip to the Caribbean can be stressful. From choosing your island destinations to hand-picking the right excursions, it's easy to get overwhelmed. Our team helps you enjoy a worry-free, regret-free vacation experience without having to do it all on your own.

With Barefoot Cowboy, you can explore luxury Caribbean islands and hidden gems on a cozy charter with up to 10 guests. We have a wide selection of activities and excursions for every type of traveler in your party—whether you’re thrill seekers or beach bums!

Our customization options include:

  • Departure and arrival times

  • Destinations

  • Cuisine and drinks

  • Activities

  • Itinerary schedule

Scroll down to explore some of your trip options. You can personalize as much as you like. If you aren’t sure how to make the most of your Caribbean getaway, our team can provide suggestions of our go-to stops (it’s one of our favorite parts of the job!).

Our Favorite Diners & Dives

Some of the best bites come from local, family-owned restaurants. Luckily, we know some of the best joints in all your favorite destinations! Here are a few of our favorite picks.

Lime Out

Pizza Pi

Dinghy's Beach Bar & Grill

Our Favorite Diners & Dives

Some of the best bites come from local, family-owned restaurants. Luckily, we know some of the best joints in all your favorite destinations! Here are a few of our favorite picks.

Lime Out

Pizza Pi

Dinghy's Beach Bar & Grill

Hidden Gems

Take a trip off the beaten path, and you’re almost guaranteed to make unforgettable memories (while avoiding the crowds). Check out some of these stunning secret destinations!

Hull Bay

Brewer's Bay

Hidden Gems

Take a trip off the beaten path, and you’re almost guaranteed to make unforgettable memories (while avoiding the crowds). Check out some of these stunning secret destinations!

Hull Bay

Brewer's Bay

Your Dream Vacation Awaits You

Give us a call to get started, or download our Preferences Sheet and plan your perfect Caribbean escape now.

Barefoot Cowboy logo

GO BAREFOOT!

Connect with US

All rights reserve | ©2024. | Powered by ROI Online | Privacy Policy