Visit Island Paradise

From quiet, secluded beaches to bustling nightlife, each Barefoot Cowboy adventure is custom-tailored to include your favorite destinations from the British or U.S. Virgin Islands. Explore your options below to plan out your one-of-a-kind adventure.

Visit Island Paradise

From quiet, secluded beaches to bustling nightlife, each Barefoot Cowboy adventure is custom-tailored to include your favorite destinations from the British or U.S. Virgin Islands. Explore your options below to plan out your one-of-a-kind adventure.

The British Virgin Islands

Comprising 4 big islands and dozens of smaller ones, the British Virgin Islands are known for their reef-lined beaches, crystal clear water, and perfect surf. These are some of the most untouched islands on the planet—the ideal mix of seclusion and luxury.

As the largest and most populated island in the BVI, Tortola has plenty of fun to keep you busy. It features white sand beaches, lush mountains, and ancient ruins alongside high-end shopping destinations.

Explore Soper’s Hole and Trellis Bay. Enjoy the surf at Cane Garden Bay. If you're looking to wind down or let loose, you’ll find both the landscape and the locals to be warm and friendly.

Bucket-list activities:

  • Enjoy top dining and diving at Cane Garden Bay
  • Explore the clear waters of Smuggler’s Cove
  • Join the famous Full Moon Party at Trellis Bay for some of the best BBQ around
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Known for its rich history and yacht anchorages, Jost Van Dyke is dotted with sandy beaches, casual bars, and delectable restaurants. It’s the smallest of the main islands but full of personality, great views, and stunning coral reefs.

White Bay, named after its bright white sand beach, is a good place to dive, eat, and drink. One of Jost’s hidden gems is the Bubbly Pool. This natural formation creates bubbling, cool water that mimics a jet spa.

Bucket-list activities:

  • Snorkel at White Bay and stop by Jost Van Dyke Scuba for souvenirs
  • Enjoy the famous Pain Killer drink at the Soggy Dollar Bar
  • Hike to the Bubbly Pool, a natural wonder full of fish and rushing bubbling water
  • Fill your stomach and your pockets with fresh eats and souvenirs from Foxy’s Bar
  • Hendo’s, One Love Bar & Grill, & so many great beach bars are calling
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A low-lying coral island, Anegada is known for secluded beaches like Loblolly Bay and Cow Wreck Beach. The island is home to flamingos, rock iguanas, and rare plant species like sea lavender. It’s the perfect place to explore nature, kick up your feet, and relax.

Snorkel at Horseshoe Reef to see all kinds of tropical fish, lobster, and live conch. Scuba divers can explore shipwrecks in Wreck Alley, and casual swimmers will love the finds at Cow Wreck Beach.

Bucket-list activities:

  • Explore miles of white sand and delicious eats at Loblolly Bay
  • Spot hundreds of roosting flamingos at Flamingo Pond
  • Stop by Cow Wreck Beach and visit the large gift shop, bar, and restaurant
  • Stop for fresh seafood and refreshing smoothies at the Anegada Reef Hotel
  • Visit Tipsy’s Beach Bar for tacos and mixed drinks on the beach
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Best known for The Baths and its white sandy beaches, Virgin Gorda includes prime snorkeling destinations and walking trails. It’s the third-largest BVI and one of the most popular destinations in the Caribbean.

Explore unforgettable sites at the Baths, a natural landmark containing hidden rooms, grottos, and caves formed by giant granite boulders. Then take a short hike over to Devil’s Bay National Park for beautiful views, soft sand, and snorkeling in the crystal clear waters.

Bucket-list activities:

  • Snorkel at the Baths and see how many hidden gems you can discover
  • Try the best pulled-pork and BBQ in the BVIs at Hog Heaven
  • Hike up to the lookout tour at Gorda Peak to view nearby islands
  • Visit the North Sound’s Bitter End Yacht Club
  • Have dinner at the beautiful Saba Rock restaurant
  • See the pirate show at Leverick Bay
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Located at the southern tip of the British Virgin Islands archipelago, Norman Island is a privately owned island known for snorkeling, diving, and other fun. It’s easy to see why it’s one of the islands that inspired Robert Louis Stevenson's pirate novel Treasure Island.

The biggest attraction on Norman Island is the mysterious caves surrounding the land that provide protection for passing ships, one reason why pirates liked to visit. The Indians and Key Cay are great snorkeling spots with plenty of tropical fish and reefs to explore.

Bucket-list activities:

  • Check out the Norman Island Caves and have your own pirate adventure
  • Visit the Indians for beautiful shallow coral reefs full of fish of all shapes and sizes
  • Keep your hunger at bay with martinis, burgers, and lobster jambalaya from Pirates Bight Restaurant & Bar
  • Visit The World Famous Willy T’s for cocktails, lunch, music and dancing

This small, isolated, and charming island serves as a mooring haven for yachts. It’s a picturesque stop known for its amazing eats, calm beaches, mooring balls, and cozy bars. The calm air and gentle sea are perfect for soaking up the sun.

Cooper Island provides a small mooring ball, including boaty balls that you can reserve (as they go fast!). There are also a couple of anchor fields and great snorkeling places. Enjoy eats at the open-air, upscale restaurant and plan for some shopping at the local boutiques.

Bucket-list activities:

  • Rest your drink on the tables in the water as you swim, snorkel, and dive
  • Spot the lights of Tortola and listen for the goats on the hills in the morning
  • Visit the Rum Bar for fried Mahi Mahi, lobster, craft beer, burgers, and fish and chips
  • Look for turtles sleeping underwater in the soft sand and eelgrass
  • Enjoy a delicious meal with an ocean view while barefoot
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This British Virgin Islands destination offers five powder white sand beaches, luxurious spas, tennis courts, pools, dive shops, and world-class dining. As the largest private island in the BVI, Peter Island is located about 5 miles southwest of Road Town, Tortola.

Deadman’s Beach is a must-see stop on the island, regarded as one of the world's most romantic beaches because of its quiet waters and dining options. Head over to Key Cay at Norman Island to end your day with snorkeling, swimming, diving, and cave exploring.

Bucket-list activities:

  • Reserve dinner reservations at the beach bar to enjoy a wide variety of food selections from seafood to beef, pork, and chicken
  • Enjoy white sand beaches, clear water, and swells breaking over the coral formations
  • Visit the spa for some much-needed pampering and relaxation
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U.S. Virgin Islands

These gorgeous islands offer breathtaking beaches, unforgettable excursions, and memories you’ll cherish for a lifetime. The great thing about staying in the U.S. Virgin Islands is no passport is required. Just hop aboard and get ready to set sail!

Best known for its picture-perfect beaches and spectacular diving spots, St. Thomas is bursting with energy and fun. The island boasts a world-renowned golf course, relaxing shopping, world-class dining, and a nightlife unlike any other.

Snorkel in Christmas Cove’s crystal blue waters to catch a glimpse of diverse wildlife like conch, sea turtles, and spotted eagle rays. Magen’s Bay, hailed as one of the world's most stunning beaches, is perfect for swimming and snorkeling and a short walk from restaurants and bars. Hull Bay is considered one of the best places to surf on the island, and Buck Island provides breathtaking snorkeling excursions you’ll never forget.

Bucket-list activities:

  • Hang out with the locals at Hull Bay Beach
  • Enjoy food and drinks at The Shack
  • Unwind with live music on Sunday Funday at Dinghy's Beach Bar
  • Snorkel with turtles and sting rays at Brewer's Bay
  • Soak up the sun and snorkel at the world-famous Magen's Bay
  • Enjoy homemade pizza off a boat from Pizza Pi in Christmas Cove
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St. John, the smallest of the U.S. Virgin Islands, has some of the most incredible, unspoiled beauty you’ll find in the Caribbean. Two-thirds of the island are dedicated to the Virgin Islands National Park, best known for its scuba diving, snorkeling, and hiking excursions. Originally settled by the Arawak and Carib Indians, the island’s history is as rich as its landscape.

Cinnamon Bay offers a variety of water sports from snorkeling and kayaking to sailing and windsurfing. Trunk Bay, a world-class stretch of white sand and turquoise water, features a an underwater trail full of lobster, tarpon, sea turtles, and squid. At Caneel Bay, the calm waves, crystal clear water, and soft sand make for the perfect snorkeling trip.

Bucket-list activities:

  • Explore miles of hiking trails through the tropical rainforest in the national park
  • Enjoy tacos and cocktails at the floating taco stand, Lime Out
  • Take a taxi up to the Windmill bar for stunning views, amazing drinks, and live music
  • Relax at the stunning beach Cinnamon Bay
  • Enjoy crystal sands and an underwater nature trail at the famous Trunk Bay Beach
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Not Sure Where You Want to Go?

We’re here to help! Reach out to the team at Barefoot Cowboy, and we’ll work together to create a personalized vacation experience designed around your party’s interests, lifestyle, and preferences.

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