Top 10 Must-Visit Islands in the Caribbean for an Unforgettable Charter Experience
The Caribbean is home to 700 islands and inlets, all with their own unique charm. On a single charter vacation on the Caribbean Sea, you could experience everything from cacti to palm trees and, of course, plenty of soft, sandy beaches.
But which islands are, in our opinion, the best of the best? Where can you find bucket-list excursions, breathtaking views, and unforgettable hidden gems on a week- or two-week-long vacation in the Caribbean?
In this blog, we’re sharing our must-see Caribbean island destinations and the activities you won’t want to miss when you visit each one.
The Top 10 Caribbean Islands to Visit for an Unforgettable Charter Vacation
1. Tortola – British Virgin Islands (BVI)
The bustling heart of the BVIs, Tortola blends local flavor with upscale charm. It’s the largest island in the British Virgin Islands and is best known for its beaches, marine activities, and wildlife.
Whether you’re relaxing on the beach or hiking Sage Mountain, this island offers something for everyone.
Why you’ll love it:
Snorkeling in the many hidden coves
Kiteboarding and windsurfing
Plenty of historical sites, parks, and hiking trails
The famous Full Moon Party at Trellis Bay
2. Jost Van Dyke – BVI
Famous for its barefoot beach bars and calm bays, Jost Van Dyke is paradise for those looking to relax and enjoy some good island vibes with their toes in the sand. It’s one of the smaller BVI destinations, but its vibrant culture and history have led to mouth-watering cuisine you won’t find anywhere else.
Jost Van Dyke offers panoramic ocean views, quaint seaside villas, and a wide variety of sea life. It’s perfect for anyone who loves unforgettable adventures, soaking in new cultures, and basking in the sun on endless stretches of beaches.
Why you’ll love it:
Powder-white sandy beaches
Includes one of the world’s most visited beaches in the Virgin Islands
Scuba diving and snorkeling
Stand-up paddle boarding in the calm waters
3. Virgin Gorda – BVI
Home to the iconic Baths, Virgin Gorda is where natural beauty meets adventure. Giant granite boulders form tide pools and secret beaches that feel like another world. It’s easy to see why Virgin Gorda is known as one of the most beautiful Caribbean islands.
Virgin Gorda was once home to early African, Spanish, and Indian settlements, and remnants of those civilizations remain to this day. One of the top ruins to visit is the old Copper Mine, an abandoned Spanish mining structure where workers dug as deep as 240 feet.
Why you’ll love it:
Incredible natural wonders at the Baths National Park
Hiking at Gorda Peak
The pirate show at Leverick Bay
The best pulled pork and BBQ in the BVI
4. Norman Island – BVI
A real-life inspiration for Treasure Island, Norman is ideal for snorkeling, diving, and pretending you’re a pirate (or at least living like one). Pirates reportedly buried at least 55 chests of silver coins among the caves, most of which locals hunted down in the late 1700s. But rumors persist that more treasure could be hidden in Norman Island, just waiting to be discovered.
Norman Island’s three water-level caves make snorkeling a truly unforgettable experience. If you explore deep in the caves, you’ll feel like you’re enjoying a night dive all day long. Wild goats love to hop around the rocky island. You may even find a shipwreck while exploring the waters.
Why you’ll love it:
Shallow reefs where you can see dozens of tropical fish
Martinis, burgers, and lobster jambalaya at Pirates Bight Restaurant & Bar
Music and dancing at the famous Willy T’s
Search for hidden treasure or enjoy a quiet snorkeling experience unlike any other
5. Anegada – BVI
Flat, remote, and surrounded by reefs, Anegada is a lobster-lover’s dream and a kite-surfer’s paradise. Anegada is the northernmost of the British Virgin Islands and the only island formed out of coral and limestone rather than volcanic rock. It’s the road less traveled—and 100% worth it.
Anegada is a prime fishing destination, with local fishermen providing most of the fresh fish and lobster for the rest of the BVI. Thanks to its unique shape and huge bonefish population, it’s also a great place to test out fly fishing.
Why you’ll love it:
Horseshoe Reef, one of the Caribbean’s largest barrier reefs
Large salt ponds full of roosting flamingos
Souvenirs shopping at Cow Wreck Beach
Some of the best tacos and cocktails in the BVI
6. Cooper Island – BVI
Cooper Island is one of the “Little Sisters” islands of the BVI. The island may be small, but it’s packed with adventure and attracts group tours from around the globe. For divers, Cooper Island is a must-see thanks to “wreck alley,” a stretch of ocean where vessels were deliberately sunk to create a one-of-a-kind diving experience.
Cooper Island is entirely off the grid, making it the perfect place to unplug and unwind.
Why you’ll love it:
Tables in the water so your drink is never far away
Ice cold drinks at the Rum Bar
Searching for sleeping turtles while you snorkel
The sand is perfect for walking barefoot
7. St. Thomas – U.S. Virgin Islands (USVI)
As your likely point of arrival, St. Thomas is more than just an entryway. Explore historic Charlotte Amalie, climb the 99 Steps, or simply unwind before the real journey begins. You’ll also find vibrant nightlife and top surfing spots.
St. Thomas hosts a month-long carnival, typically from mid-April to mid-May, that includes parades, Calypso shows, Pan-O-Ramas, and J'ouvert. During Carnival season, you can enjoy a day-long food fair and explore the decorated Carnival village for live music, booths, and an amusement park.
Around Christmas time, the historic Miracle on Main Street includes carolers, Santas, steel pan battles, vendors with homemade products, and a Light Boat parade on the waters.
Why you’ll love it:
Spotting sea turtles and spotted rays while snorkeling
Live music on Sunday Funday at Dinghy’s Beach Bar
Homemade pizza aboard the floating Pizza Pi
World-class dining and top shopping destinations
8. St. John – USVI
With 60% of the island protected as a national park, St. John is a treasure trove of hiking trails, wildlife, and pristine beaches like Trunk Bay. Think of it as nature’s luxury resort. St. John is the smallest island in the USVI but packed full of adventure and incredible views.
St. John is perfect for island hopping, being only a few miles from Tortola, St. Thomas, Jost Van Dyke, and other top destinations. During your visit, you can enjoy hiking excursions in the Virgin Islands National Park, water sports in Cinnamon Bay, and crystal clear waters perfect for snorkeling.
Why you’ll love it:
Underwater nature trail in Trunk Bay
Stunning views, delicious drinks, and live music at Windmill Bar
Tacos and cocktails from the floating taco stand, Lime Out
Snorkeling, kayaking, sailing, windsurfing, and much more
9. Culebra – Spanish Virgin Islands (SVI)
Tucked away from the crowds, Isla Culebra is the definition of a hidden gem. Flamenco Beach is consistently ranked among the world’s best, and the laid-back vibe is pure magic. Windsurfing, fishing, scuba diving, and hiking are popular activities on the islands, and you can even catch tournaments in winter and spring.
On and surrounding the main island, you’ll find nature preserves full of wildlife, including the extremely rare Culebra Island giant anole. The island is also home to turtle nesting sites and the archipelago's bird sanctuaries, which are home to over 20,000 birds.
Why you’ll love it:
Flamenco Beach, the No. 2-ranked best exotic beach in the world
Incredible hiking trails with lots of wildlife to take photos of
Arid nature results in crystal clear, warm water
Beached tanks from WWII turned into art by nature and graffiti artists
10. Vieques – SVI
Home to the world’s brightest bioluminescent bay, Vieques is ideal for night kayaking, wild horse spotting, and slow-paced living. This quiet, peaceful island retreat is a true escape from the modern world.
Vieques has dozens of undiscovered beach coves and the largest natural wildlife refuge in the Caribbean. Horseback riding is one of the top activities on this island, along with hiking and exploring the historical attractions and unique architecture.
Why you’ll love it:
Nature’s best light show at Mosquito Bay
Taking in art and history at the museum at El Fortin
Tasting Puerto Rico’s rich and decadent cuisine
Snorkeling in the calm waters of La Chiva Beach
Ready to See These Islands for Yourself?
Whether you tour the U.S. Virgin Islands, British Virgin Islands, Spanish Virgin Islands, or every one of them, each island on this list offers an unforgettable experience that you’ll want to enjoy again and again. And we’re here to help you start checking off those trips from your bucket list!
Barefoot Cowboy creates once-in-a-lifetime vacations based on your party’s preferences. Most trips rush you. Ours revolve around you. From selecting the perfect islands to curating the right mix of adventure and R&R, every detail is designed around your idea of the perfect getaway. No stress. Just salty air, sunny skies, and unforgettable moments.
Let’s make your dream charter a reality! Reach out to Barefoot Cowboy today and start planning the Caribbean escape your future self will thank you for.
