The Caribbean is a true boater’s paradise, and not just because of its crystal clear waters, pristine landscapes, and untouched coral reefs. When you choose to experience the Caribbean via yacht, you gain exclusive access to islands that can only be reached by fellow sailors. For a relaxing holiday that immerses you in the authentic Caribbean experience, there’s no other way to travel!
With 7,000 islands to explore, the hardest part of planning a Caribbean sailing holiday is choosing where to visit. Ready to make the most of your freedom?
Here are eight spectacular Caribbean islands that reward those who make the journey by sea:
- Tintamarre, St. Martin
- Culebra, Puerto Rico
- Jost Van Dyke, BVI
- Anegada, BVI
- St. John, USVI
- Tobago Cays, Grenadines
- Elbow Cay, Abacos, Bahamas
- Shroud Cay, Exumas
Keep reading to discover which Caribbean islands’ sailing spots are best for your holiday and how to access them from a Dream Yacht Charter base.
Sailing the Hidden Caribbean: Islands Only Accessible by Boat
Tintamarre, St. Martin
There’s only one way to describe the beauty of Tintamarre: frozen in time. Because it’s both uninhabited and protected as a nature reserve, the small island is filled with untouched natural attractions everywhere you look.
Tintamarre is also conveniently located less than one hour off the northeast coast of the much larger St. Martin. For easy sailing, leave from our Dream Yacht Charter base in Marina de L’Anse Marcel. When you arrive, the first thing you’ll notice is a stunning stretch of powdery white beaches – all blissfully free from crowds!
If you love hiking, you’ll love trekking the island’s diverse terrain, which spans rocky cliff tops overlooking azure water to great grassy plains. Marine enthusiasts will also love Tintamarre for its exceptional snorkelling, especially along the island’s western edge. Keep an eye out for sea turtles, rays, and tropical fish, all set against the backdrop of the island’s vibrant reef system.
To end your Tintamarre day on a high note, catch the sunset from the western shore.
Culebra, Puerto Rico
Ready to learn one of the Caribbean’s best-kept secrets? Even though most travellers haven’t heard of them, the Spanish Virgin Islands are among the most attractive in the region. Our favourite island is, of course, Culebra, home of magnificent yet underdeveloped beaches and jaw-dropping snorkelling.
Sailors with Dream Yacht Charter can reach Culebra from our base in St. Thomas, USVI. The journey is about 25 nautical miles across calm, turquoise waters. Though it can take about five hours, this stretch of sailing offers spectacular views and plenty of opportunities to spot marine life!
Once in Culebra, Flamenco Beach is a must. It’s consistently ranked among the world’s best beaches for its white sand, lush green hills, and impossibly blue waters. If any snorkelers are aboard, stop by Carlos Rosario Beach to splash around coral gardens with tropical fish.
With two-thirds of Culebra dedicated to wildlife refuge, this island embodies the unspoiled beauty of the Caribbean.
Jost Van Dyke, BVI
If you picture yourself adventuring through the Caribbean like storybook explorers, Jost Van Dyke is the island for you. Though it’s just six square kilometres, this tiny island packs enormous personality, natural beauty, and plenty of old-timey charm.
The island’s most famous attraction is White Bay. Unlike the uninhabited islands on this list, here you’ll find charming local beach bars nestled between swaying palm trees. The Soggy Dollar Bar is especially well-known for inventing the Painkiller cocktail.
For a less indulgent activity, head inland to trek Jost Van Dyke’s iconic hiking trails. Many lead to panoramic viewpoints, so be sure to bring your camera!
Jost Van Dyke is located just 3 miles northwest of Tortola, so simply sail directly from Dream Yacht Charter’s Tortola base in Hodges Creek Marina.
Anegada, BVI
While many islands in the British Virgin Islands formed from volcanoes, Anegada is a flat coral atoll. It rises just 28 feet above sea level at its highest point, making Anegada a geographically unique getaway that true boaters will appreciate.
With a distinctly different landscape from the rest of the BVI, visitors can explore salt ponds, shallow swimming holes, and the world’s fourth-largest barrier reef. It’s considered a diver’s and snorkeler’s paradise, especially if you love exploring historical shipwrecks!
Anegada is also renowned for serving up the Anegada lobster at its many beachfront restaurants. A bit more inland, you can also rent a moped or Jeep to traverse the island’s incredibly scenic roads.
To reach Anegada, sail about 2-3 hours from Dream Yacht Charter’s Tortola base.
St. John, USVI
For a blend of natural splendour and easy access to tourism resources, head to St. John. Though it’s one of the main destinations of the U.S. Virgin Islands, nearly two-thirds of its territory is protected by the Virgin Islands National Park.
For example, Trunk Bay has a pristine underwater snorkelling trail you can experience with a local guide. Inland, you’ll also find 20+ trails protected by the park, offering hiking enthusiasts easy access to the tropical forest. For waterfront dining and boutique shopping, head to Cruz Bay for a day of laid-back sophistication.
Dream Yacht Charter travellers can reach St. John from our base in St. Thomas, USVI. Unlike the day-trippers arriving by ferry, your yacht can access secluded bays and hidden beaches across the island.
Tobago Cays, Grenadines
Picture yourself sailing between five untouched Caribbean islands, surrounded by a perfect horseshoe-shaped coral reef – and having all of that beauty entirely to yourself. That’s what you can expect from the Tobago Cays, a protected marine park with white sand beaches, crystal-clear waters, and extraordinary marine biodiversity.
Anyone can find something to love in Tobago Cays, but snorkelling enthusiasts are particularly drawn to the islands. The Cays’ pristine coral reefs create the perfect conditions for world-class snorkelling, including shallow, clear waters and an array of marine life. Above water, hikers can enjoy small, relaxing trails leading to stunning panoramic viewpoints.
Dream Yacht Charter travellers can reach this dreamy destination from our bases in Grenada or Martinique. With plenty of stops along the way, the journey alone will be worth it!
Elbow Cay, Abacos, Bahamas
If you’re seeking a mix of colonial charm and breathtaking natural beauty, Elbow Cay will be your dream Caribbean escape. This slim, six-mile slice of paradise in the Abaco Islands features pristine beaches dotted with authentic Bahamian character everywhere you look.
Dream Yacht Charter sailors can easily reach Elbow Cay from our base in Marsh Harbour on Great Abaco. After a short yet stunning journey, you’ll be greeted by a picturesque, well-protected harbour and Hope Town’s iconic candy-striped lighthouse.
For dramatic surf and beautiful beach panoramas, head to the eastern Atlantic-facing shore. For leisurely swimming and colourful snorkelling spots, visit the Western coastline’s calm, protected waters. For a truly magical experience, don’t miss Tahiti Beach on the southern tip. It’s famous for a crescent of powdery white sand beach and dream-like blue waters!
For a taste of old Caribbean, wander through Hope Town’s charming streets. With no motorised vehicles allowed, you’ll feel like you’ve stepped back in time.
Shroud Cay, Exumas, Bahamas
Nature enthusiasts hoping to experience true Caribbean wilderness will feel at home in Shroud Cay. The northern gateway to the Exuma Cays Land and Sea National Park, this uninhabited island features protected ecosystems of winding mangrove channels.
The best part? Visitors can explore this interior waterway network on a dinghy or kayak. As you head deeper into the island, you’ll feel uniquely immersed in the wild Caribbean jungle. For sweeping views of the Exuma Sound, head to Camp Driftwood on the eastern creek. You’ll find a viewing platform perfect for panoramic photography.
But the channels aren’t the only highlight of this island. Marine enthusiasts also love exploring the surrounding waters thanks to their exceptional clarity and white sand bottoms.
Sailors with Dream Yacht Charter can access this hidden gem from our base in Nassau. Though it requires careful planning, Shroud Cay rewards anyone who makes the journey with an unforgettable natural experience.
Your Caribbean Sailing Adventure Awaits
Ready to explore the Caribbean’s hidden treasures aboard a pristine yacht charter? No matter your boating experience, sailing with Dream Yacht Charter unlocks exclusive access to idyllic islands and customisable itineraries.
Contact us today to start planning your sailing adventure to these exclusive island gems. With Dream Yacht Charter bases strategically located throughout the Caribbean, your dream holiday awaits!
