Sailing the USVI & BVI: What to Pack for the Perfect Charter Vacation

The U.S. Virgin Islands (USVI) and British Virgin Islands (BVI) offer the ultimate sailing paradise—crystal-clear waters, secluded beaches, and endless adventure.

Space is limited on a boat, and Barefoot Cowboy provides plenty of amenities. But you don’t want to be thousands of miles away from home and realize that you’re missing something essential.

When you're embarking on an action-packed vacation aboard a charter like Barefoot Cowboy, packing smart is key to enjoying your trip stress-free. Here’s your ultimate packing guide to ensure smooth sailing, onboard comfort, and shore-side fun.

1. Essential Clothing for Sailing on the USVI & BVI

The Caribbean has warm, balmy weather year-round. But the occasional southern gale can cool things off on the water, meaning packing a variety of clothes is a must. You can use a site like Weather Underground to keep an eye on the forecast for your trip.

• Lightweight, Breathable Clothing – Opt for moisture-wicking fabrics like linen or quick-dry polyester. Loose, airy clothing will keep you cool on deck. Be sure to bring a causal outfit or two to wear for island dining as well.
  

• Swimsuits (Several!) – You’ll be in and out of the water all day, so bring a few to rotate.
  

• Sun Protection – Pack a wide-brimmed hat, UV-protection sunglasses, and reef-safe sunscreen (chemical sunscreens can harm marine life).
  

• Boat Shoes & Sandals – Choose non-marking, slip-resistant deck shoes for safety onboard–ideally a pair with good arch support you can use while exploring the islands. Don’t forget to pack comfortable sandals or flip-flops for beach time as well.
  

• Lightweight Cover-Up or Rash Guard – Perfect for sun protection when snorkeling or relaxing on the boat.

2. Gear for Your Favorite Beach & Water Activities

When you’re on the water, you’re going to want to make the most of it! Plan for hours of ocean fun by packing these essentials:

• Snorkel Gear – Our charter provides equipment, so you don’t have to pack snorkel gear if you don’t want to. However, some vacationers prefer to bring their own well-fitted mask to ensure comfort.
  

• Dry Bag – Keeps your phone, camera, and essentials dry when heading to shore.
  

• Packable Beach Towel or Sarong – Quick-dry and compact options are best.
  

• Underwater Camera or Waterproof Phone Case – Capture stunning marine life and epic adventures.

3. Must-Have Grabs for Onboard Entertainment

Life aboard Barefoot Cowboy is about relaxation, adventure, and making memories. While the crew takes care of everything, packing extra tech and activities can enhance your party’s experience. We recommend:

• Books or E-Reader – Enjoy a novel while lounging on deck. If you’re an avid reader, taking a tablet with multiple books could be an even better option.
  

• Portable Speaker – For playing your favorite tunes while sailing (Bluetooth recommended) or dance parties on deck.
  

• Journal or Sketchbook – Capture your thoughts or sketch the breathtaking landscapes. Notepads are also handy for keeping track of bucket list activities and which animals you’ve spotted.
  

• Cards & Travel Games – Perfect for fun nights under the stars. We have a few of our favorites, but you’ll want to grab yours if your party has specific go-to games.
  

• Binoculars – Spot dolphins, distant islands, or other boats on the horizon. It’s a favorite for everyone from birders to kiddos experiencing the islands for the first time.
  

• GoPro or Drone – Document your trip from every angle. 

4. Your Preferred Specialty Drinks

While your most memorable meals will probably be shared on the islands, you’ll want to ensure your taste buds are satisfied aboard the charter as well. 

We’ll include a supply of your favorite drinks, but if you have a particular bottle you want to include, be sure to let us know ahead of time.

5. Packing Tips for Ultimate Comfort & Fun on Excursions

Space can be limited aboard the charter, especially when you’re traveling with a large party. Follow these tips to make packing (and unpacking) easier:

• Bring a Soft-Sided Duffle Bag – Hard suitcases are difficult to store on a boat. A soft, collapsible bag, like this one or this one, will fit the limited space better.
  

• Use Packing Cubes – Keep items neatly stored and easy to access in your bag. Check out these top-rated travel packing organizers from Amazon if you don’t know where to start.
  

• Pack Minimal Toiletries – The boat provides essentials, like shampoo, conditioner, and Body wash, so only bring what you need. A toothbrush, makeup, and any prescription treatments are all you'll need!
  

• Small Daypack – A small backpack, shoulder bag, or fanny pack is all you need to carry your essentials on day trips––and it’s a lot more comfortable to tote around than a heavy purse.
  

• Cash in Small Bills – Some local spots (and cabs) don’t accept cards. You’ll also want to leave your American Express at home. MasterCard and Visa work well in the Caribbean, but many places won’t accept Amex.

  
  

Ready to Set Sail?

At Barefoot Cowboy, we believe your vacation should be seamless, personalized, and stress-free. By packing smart, you’ll be ready to embrace every unforgettable moment the USVI and BVI have to offer.

Dreaming of sailing the crystal blue waters of the Caribbean? We’d love to have you! Reach out to our crew today to book your dream sailing adventure.

Go barefoot, make memories, and let the adventure begin!