Traveling through the British Virgin Islands (BVI) and U.S. Virgin Islands (USVI) on a charter boat is a dream experience. Turquoise waters. Hidden coves. The freedom on the sea. 

But for vacationers who haven’t taken a charter excursion before, it’s easy to feel out of your element—or even a little overwhelmed.

If it's your first time on a charter, a little preparation can make your voyage seamless and unforgettable. From choosing the right crew to packing wisely, these 10 essential tips will ensure your adventure is full of good memories only.

10 Things to Remember Before Your First Charter Vacation to the Caribbean

1. Choose the Right Charter

Not all charters are created equal. A one-size-fits-all itinerary may not give you the dream vacation you envision. In fact, many people find that they spend too much time on activities that they weren’t as interested in and not enough time doing what they really want to do.

Instead of booking the first charter you see, look for a crew that customizes your trip to your preferences—whether that means relaxed beach days, adventurous snorkeling excursions, or a mix of both.

2. Communicate Your Preferences Before You Set Sail

Charters that prioritize customization will take steps to ensure your vacation is just right for your party. But they can’t do that if they don’t know what you like (and don’t like).

Before boarding, be sure to share your:

• Food and drink preferences (including allergies)

• Desired balance of activity vs. relaxation

• Must-visit locations and bucket list experiences

• Special occasions like anniversaries or birthdays
  

A good charter crew will use this information to curate a personalized itinerary that makes every moment count. And you may find a few surprises sneaked into your trip to make it even more special!

3. Pack Light

Storage space on charter boats is limited. Instead of hard, bulky suitcases, bring a soft-sided rolling duffle bag that’s easy to stow. Other essentials include:

• Quick-dry clothing and swimsuits

• Flip flops and comfy shoes for island excursions

• Reef-safe sunscreen and sunglasses

• A light rain jacket for occasional showers
  

READ: What to Pack for the Perfect Caribbean Charter Vacation

4. Should You Worry About Motion Sickness?

Very few people get seasick aboard the Barefoot Cowboy. Even those who are usually prone to motion sickness in cars often have no problem with nausea on their trip.

Still, if motion sickness is something that worries you, it's not a bad idea to pack remedies like:

• Over-the-counter meds (Dramamine or Bonine)

• Ginger chews or tea

• Pressure point wristbands

• Motion sickness patches (Behind the ear application)
  

The best cure for motion sickness, in our experience, is to focus on the horizon and get fresh air on deck!

5. Respect the "Barefoot Rule" Onboard

Most sailing yachts (including Barefoot Cowboy) follow the no-shoes-on-deck rule to protect the boat’s surfaces and prevent slipping. Pack non-marking, slip-resistant boat shoes if you need footwear, but be ready to embrace island life—barefoot style!

If you have foot issues (like plantar fasciitis, bunions, or tender toes), exceptions can always be made. Just let the crew know ahead of time!

6. Be Flexible

Island time is a real thing, and once you get used to it, you’ll never want to leave. One of the best parts of a Caribbean sailing vacation is the relaxed pace. 

Weather and conditions may require small adjustments to your itinerary, but that’s part of the adventure! Trust your crew to guide you to the best spots based on current conditions.

7. Embrace the Disconnect

While some yachts offer limited WiFi, signal strength can be spotty. Use this time to truly unplug and unwind. Trade screen time for snorkeling, stargazing, and making memories.

💡 Want to stay connected? Download maps, books, and playlists before your trip, and enable offline mode on essential apps.

8. Tipping Your Crew—What’s the Norm?

Your crew works hard to ensure a flawless trip. In the Caribbean, the customary gratuity for excellent service is 15-20% of the charter cost, given at the end of your voyage. While cash is the go-to at restaurants or souvenir shops on the islands, Venmo and Zelle are the preferred options for the charter crew.

9. Relax & Enjoy

One of the biggest advantages of a fully crewed charter is that every detail is handled for you. From gourmet meals to navigating the best anchorages, all you need to do is soak in the experience.

Your only job? Kick back, relax, and enjoy the Caribbean breeze. 

10. Expand Your Experience by Embracing Sailing Life 

While you don’t need any sailing experience, knowing a few basic terms can enhance your trip—especially for those interested in sailing. These are the ones many sailors use:

• Bow – Front of the boat

• Stern – Back of the boat

• Port – Left side

• Starboard – Right side

• Galley – The kitchen

• Head - Bathroom/ Restroom
  

Your crew will handle everything, so learning to talk like a sailor certainly isn’t needed. But if you’re curious, the crew is usually happy to help you embrace sailing life—and may even let you assist with hoisting sails or steering!

Ready to Set Sail?

Whether you’re looking for adventure, relaxation, or a mix of both, Barefoot Cowboy ensures your first charter experience is unforgettable. Barefoot Cowboy specializes in tailoring every aspect of your journey, ensuring your vacation is as laid-back or action-packed as you like.

Whether you’re dreaming of secluded beaches and naps in the sand or active excursions full of jaw-dropping moments, we’ve got you covered!

Go barefoot, embrace the waves, and create memories that last a lifetime! Contact us today to start planning your Caribbean escape, or click here to see our available vacation dates.