A Day Aboard the Barefoot Cowboy: What to Expect on Your Caribbean Charter Vacation

When you step aboard Barefoot Cowboy, every day is designed around your comfort, fun, and freedom. There’s no rigid schedule or requirements. You and your party set the pace.

But for most guests, the typical day follows a similar flow. It’s all about taking it easy while making the most of every minute.

So what should you expect from your vacation? Here’s a glimpse into what the average day looks like aboard our luxury charter in the Caribbean.

A Quiet Morning & Fresh Breakfast

There’s no alarm clock on Barefoot Cowboy. Everyone wakes up when they’re ready, whether that means catching the sunrise over the water or sleeping in. With five spacious cabins (each with its own en suite bath), you’ll have all the privacy you need to start the day refreshed at your own pace.

Most guests are ready to go at 8:30 a.m., where we begin with a home-cooked breakfast prepared by our crew. Think fresh fruit, eggs and bacon, and maybe even mimosas or Bloody Marys to set the mood.

Meals are based on your party’s taste preferences and dietary requirements, so people with allergies or picky eaters are always taken care of.

Setting Sail for a New Destination

After breakfast, we get underway toward your next adventure: a new island, a hidden beach, or maybe a snorkeling hotspot. We typically create a loose itinerary for island hopping to hit the best Caribbean destinations, including hidden gems in the U.S. Virgin Islands, British Virgin Islands, and Spanish Virgin Islands.

While we’re on route, guests can relax on the trampolines at the bow, stretch out on a beanbag, or take in the view from the shaded flybridge (complete with a wet bar and ice makers). Feel free to read, snap some pics, or let loose with friends and family.

Island Adventures

Once we arrive, the options are endless. Dive into the turquoise water for snorkeling among tropical fish, try paddleboarding or kayaking, or simply lie back and enjoy the sun.

If you’re in the mood for more, scuba diving and fishing can be arranged. Just let our crew know what you want to do!

On land, you might enjoy beachcombing, hiking, or swimming from the shore. Lunch is flexible too, served onboard or at one of the Caribbean’s famous beach bar restaurants.

Afternoon Relaxation & Sunset Vibes

By late afternoon, the boat eases into “happy hour” mode. Around 5:00 p.m., guests gather for appetizers and the drink of the day, often with a signature cocktail in hand as the sun paints the sky.

It’s the perfect chance to laugh, share stories, or simply soak in the view from the open-air deck.

Dining & Evening Fun

Dinner is typically served between 6 and 7 p.m. at our outdoor dining table, where you’ll enjoy chef-prepared meals with the sunset as your backdrop. Depending on our location, if you’d rather enjoy a fine dining experience, we’ll swap supper on deck for top-rated Caribbean cuisine at one of our favorite restaurants.

Evenings on Barefoot Cowboy are all about choice: theme parties, dancing on the flybridge, playing cards or mahjong, karaoke, chatting with friends, or listening to music under the stars.

We’ve even hosted Super Bowl viewings on our onboard TV, with reliable Starlink WiFi to keep you connected when you want to be.

When the night winds down, you can head to bed whenever you please, knowing tomorrow brings another day of unforgettable memories.

The Barefoot Cowboy Difference

What truly makes each day aboard the Barefoot Cowboy special is the freedom to tailor your trip to your preferences. Whether you’re craving adventure or relaxation, we accommodate up to 10 guests in comfort, with food, drinks, and personalized service included in your charter price.

We don’t just offer a vacation. We create the experience of a lifetime. With every sunrise, sunset, and starry night on the water, you’ll be making memories that’ll last forever. Reach out to our crew today to plan your unforgettable getaway!