Our experience with Barefoot Cowboy Catamaran Charter was absolutely incredible! From the moment we stepped aboard, Captain Roy Pat, Chef Natalie, and Pirate Pete (the cutest first mate ever! 🐶) made us feel welcome and at home. The boat was clean and well-maintained, and the service was top-notch. Captain Roy Pat expertly navigated us from island to island, tailoring the itinerary perfectly to... More

Our experience with Barefoot Cowboy Catamaran Charter was absolutely incredible! From the moment we stepped aboard, Captain Roy Pat, Chef Natalie, and Pirate Pete (the cutest first mate ever! 🐶) made us feel welcome and at home. The boat was clean and well-maintained, and the service was top-notch. Captain Roy Pat expertly navigated us from island to island, tailoring the itinerary perfectly to our group’s preferences. Chef Natalie’s meals were next-level—every dish was fresh and delicious. Whether we were enjoying a gourmet meal on deck, snorkeling in caves, jumping off the Willy T, or just soaking in the stunning views, every moment felt like paradise. If you're looking for a truly unforgettable catamaran charter experience, this is it! We can't recommend Barefoot Cowboy enough and can't wait to book again! Less

Simply incredible!!! We sailed with Captain Roy Pat, Nathalie and Pirate Pete in November 2024 for Thanksgiving. We were a large group: four adults and six teenage boys and it was the vacation of a lifetime. From the moment we arrived, the hospitality, service, food and fun was amazing!! We truly can’t express how much fun we all had sailing from island to island in the BVIs. Barefoot Cowboys is ... More

Simply incredible!!! We sailed with Captain Roy Pat, Nathalie and Pirate Pete in November 2024 for Thanksgiving. We were a large group: four adults and six teenage boys and it was the vacation of a lifetime. From the moment we arrived, the hospitality, service, food and fun was amazing!! We truly can’t express how much fun we all had sailing from island to island in the BVIs. Barefoot Cowboys is a beautifully appointment catamaran and Captain Roy Pete and Natalie truly cater to each guests needs prior to and during your trip. Our week was filled with adventure, excitement, excellent fishing, beautiful blue waters, white sand beaches, and so much more. We all ABSOLUTELY LOVED every minute of the trip and would highly recommend booking a charter with Barefoot Cowboy. You won’t be disappointed. This is a trip that you won’t soon forget! Less

This was the best family vacation we ever had! Roy and Natalie were incredible hosts! From accommodations to the food to the fun! Highly recommend

We sailed with Roy Pat, Natalie and pirate Pete June 2024. It was without a doubt the most amazing vacation. Words can’t describe the hospitality that was received and the friendships that were made. I highly recommend sailing with Barefoot Cowboy, simply the best!!🩷👣🤠... More

We sailed with Roy Pat, Natalie and pirate Pete June 2024. It was without a doubt the most amazing vacation. Words can’t describe the hospitality that was received and the friendships that were made. I highly recommend sailing with Barefoot Cowboy, simply the best!!🩷👣🤠 Less

Everything about our experience with Roy Pat and Natalie on Barefoot Cowboy was exceptional from start to finish!!

Captain Roy and First Mate Natalie were amazing! We felt so spoiled as we enjoyed beautiful sailing each day. The Catamaran is the best around with great seating for optimal views on second level. Natalie set the tables and made each meal gourmet. I highly recommend this adventure! First Class!... More

Captain Roy and First Mate Natalie were amazing! We felt so spoiled as we enjoyed beautiful sailing each day. The Catamaran is the best around with great seating for optimal views on second level. Natalie set the tables and made each meal gourmet. I highly recommend this adventure! First Class! Less

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 ... More

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 for anyone looking for a luxury adventure in the BVIs! Less

Absolutely fantastic week on the Barefoot Cowboy with great friends and a wonderful crew! Captain Roy Pat and Natalie were the best! The boat was super clean and the food was excellent! Anything you want you get! AmIng trip and will definitely going to go back again!! Thanks again Roy Pat and Natalie!... More

Absolutely fantastic week on the Barefoot Cowboy with great friends and a wonderful crew! Captain Roy Pat and Natalie were the best! The boat was super clean and the food was excellent! Anything you want you get! AmIng trip and will definitely going to go back again!! Thanks again Roy Pat and Natalie! Less

It was an amazing trip. The food, hospitality and locations we visited were great. Capt. Roy Pat and Chef Natalie do it right. Can't wait to go again!!... More

It was an amazing trip. The food, hospitality and locations we visited were great. Capt. Roy Pat and Chef Natalie do it right. Can't wait to go again!! Less

Trip of a lifetime! Thanks again for showing us around the islands!! The food, drink and company all Amazing.

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 landsc... More

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. Less

We LOVED our experience on Barefoot Cowboy.  We have a mix of people who spend a lot of time on boats, people who have chartered like this before and some who were totally new to something like this and they ALL had a blast.  The boat itself was in great condition and was very comfortable for hanging out in and out of the water and for sleeping at night.  It was definitely large enough to feel li... More

We LOVED our experience on Barefoot Cowboy.  We have a mix of people who spend a lot of time on boats, people who have chartered like this before and some who were totally new to something like this and they ALL had a blast.  The boat itself was in great condition and was very comfortable for hanging out in and out of the water and for sleeping at night.  It was definitely large enough to feel like everyone had some elbow room or had multiple options for areas to hang out to get some space to themselves if needed.  Captain Roy Pat and Natalie Rucker are wonderful people.  And on top of that they have the best puppy Pirate Pete on board. We all immediately hit it off with them and they really did everything possible to keep everyone wanting for nothing.  They were also super informative and around to ask questions, but never felt intrusive.  Ultimately I think many of us would consider them friends now and hope we get to meet up with them during their off season.  It was the perfect trip and I hope we do it again soon! Less

We had a wonderful trip on Barefoot Cowboy with Roy Pat, Natalie, and Pete! They are very knowledgeable of the area and fun activities. Food was outstanding and Natalie’s drink of the day was always a fun treat! Highly recommend a sailing vacation on Barefoot Cowboy!... More

We had a wonderful trip on Barefoot Cowboy with Roy Pat, Natalie, and Pete! They are very knowledgeable of the area and fun activities. Food was outstanding and Natalie’s drink of the day was always a fun treat! Highly recommend a sailing vacation on Barefoot Cowboy! Less

By far one of the greatest things I’ve ever done! From the exceptional hospitality to the most breathtaking views, and not to mention the food that Chef Natalie prepared for us, Barefoot Cowboy should be on everyone’s list of vacations to take!!... More

By far one of the greatest things I’ve ever done! From the exceptional hospitality to the most breathtaking views, and not to mention the food that Chef Natalie prepared for us, Barefoot Cowboy should be on everyone’s list of vacations to take!! Less

It was the best experience you'll ever have in the Islands!!

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. Can’t wait to go back. This is a trip that you won’t soon forget!... More

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. Can’t wait to go back. This is a trip that you won’t soon forget! Less

This catamaran and the crew are first class. The crew is very attentive and accommodating. We can’t wait to sail again with Captain Roy Pat and Chef Natalie!... More

This catamaran and the crew are first class. The crew is very attentive and accommodating. We can’t wait to sail again with Captain Roy Pat and Chef Natalie! Less

It’s was all we dreamed it would be…Food was delicious and beautifully served…The staff exceptional, will go every chance we get!!!

To say this is a once in a lifetime vacation sounds cliche but its 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.... More

To say this is a once in a lifetime vacation sounds cliche but its 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. Less