Caribbean island hopping: A luxury yachting guide

Island hopping in the Caribbean delivers unrivalled freedom: mornings spent swimming in crystal-clear waters, afternoons indulging in gourmet cuisine, and evenings enjoying cocktails as the sun sets over the horizon. Whether your ideal day includes thrilling adventures, peaceful relaxation, or family-focused fun, this guide ensures every voyage is curated to your lifestyle, turning each journey into a personal and memorable escape.

The British Virgin Islands remain one of the Caribbean’s most rewarding cruising grounds, where short, sheltered passages link a string of characterful islands, each offering its own reason to drop anchor. Families love the calm anchorages and easy snorkelling, while couples are drawn to barefoot beach bars and quiet nights at anchor. 

Highlights include The Baths, perhaps the most iconic natural attraction in the BVI. Here, enormous granite boulders are scattered along the shore and shallow waters, creating labyrinth-like passages and hidden pools that are perfect for snorkelling in scenery that’s otherworldly.  

Norman Island’s sea caves are an essential stop. Legend has it that the island inspired Robert Louis Stevenson’s Treasure Island. The highlight is the glimmering sea caves, which are accessible only from the water, where sunlight filters in to create a brilliant blue with snorkelling and swimming feeling almost surreal.

Yet what defines the BVIs enduring charm is the laid-back beach bars. On Jost Van Dyke, the legendary Soggy Dollar Bar invites you to swim ashore for its famous Painkiller cocktail. The absolute prime spots are the hammocks right on the sand and tables with the best view of the turquoise water. Jost Van Dyke offers a mix of relaxation and fun, with opportunities for sailing, snorkelling, and enjoying Caribbean nightlife. 

The Bitter End Yacht Club is a legend among boaters and is only accessible by boat, making it a natural stop on any island-hopping itinerary. The resort is located in North Sound and blends barefoot luxury with a full-service marina, a watersports centre and multiple dining spots. Owners can go straight from the docks to The Buoy Room, a quintessential après watering hole that serves casual fare inspired by Caribbean flavours. It is also known throughout the BVI as the best place to watch the America’s Cup, Super Bowl, Formula 1 or Masters.

For a truly refined escape, Rosewood Little Dix Bay on Virgin Gorda, originally founded in 1964 by conservationist Laurance Rockefeller, has long been celebrated as one of the world’s premier retreats. Now fully reimagined and thoughtfully redesigned, the resort remains a shining example of ecotourism while embracing modern luxury. Set across 500 acres of pristine private beachfront, the property offers an unparalleled island experience. Guests can enjoy exquisitely appointed accommodations, inspired amenities, dynamic dining venues, and curated experiences, all designed to immerse visitors in the natural beauty and timeless elegance of the British Virgin Islands.

The resort has also become notable for its extraordinary underwater wine cellar, the first and only currently in the Caribbean. Unlike a traditional climate-controlled room, select bottles are aged some 80 feet below the surface off the coast of Virgin Gorda, where the ocean’s steady temperature, pressure, and gentle currents interact with the wine as it matures. This process develops unique aromatic complexity, while the bottles themselves emerge adorned with a natural coating of shells and coral, making each one as visually distinctive as it is flavourful. These ocean aged wines are featured exclusively in the resort’s 10 course Chef’s Table experience, pairing the wines with refined seasonal dishes that emphasise local ingredients.

The Abaco Islands, a glittering string of cays in The Bahamas, offer a cruising experience where glassy turquoise waters, soft trade winds, and pristine shorelines create the perfect canvas for exploration. Here, the journey is as indulgent as the destination: glide across luminous sandbanks to Tahiti Beach, anchor off Great Guana Cay to sip cocktails in pastel-hued harbours, or discover the tranquil charm of Green Turtle Cay, where colonial architecture meets the relaxed elegance of island life.

For those seeking refined comfort ashore, the Abacos deliver intimate resorts and boutique marinas that perfectly complement a life at sea. The Green Turtle Club Resort & Marina offers timeless colonial charm alongside a full-service marina, making it a natural sanctuary for overnight visitors with berths up to 130ft. On Elbow Cay, you can enjoy understated luxury, just steps from the iconic candy-striped lighthouse, while Abaco Beach Resort combines modern design with seamless access to provisioning and island-hopping adventures with a fabulous brunch offering every Sunday. 

Beyond the Abacos, The Bahamas reveals a spectrum of exclusive experiences for discerning travellers. Harbour Island’s pink-sand beaches offer postcard-perfect serenity, the Exumas’ private cays and swimming pigs create whimsical adventures, and Andros Island entices eco-enthusiasts with its hidden blue holes and world-class bone fishing. In Nassau, history, art, and vibrant cuisine come alive, while remote islands reward those in search of absolute seclusion.

The Ocean Club, A Four Seasons Resort is one of the Caribbean’s most refined retreats, this iconic resort on Paradise Island combines old world sophistication with modern luxury. Set along pristine beachfront and landscaped gardens, it offers sumptuous suites, private beach cabanas, championship golf and a Balinese inspired spa. 

Another hallmark of Bahamian fine dining is the Graycliff restaurant which has been a five-star culinary destination for decades. Located in a colonial mansion with an extraordinary wine cellar, it offers classic gourmet cuisine and unique experiences, from cigar rolling to wine tastings that showcase rare vintages and locally inspired dishes.

For owners seeking a mix of glamour and tranquillity, this route delivers. Begin in St. Martin, then cruise to chic St. Barts for world-class dining and shopping before escaping to Anguilla’s uncrowded anchorages and pristine beaches. It’s an itinerary that balances vibrant nightlife with peaceful seclusion.

In Gustavia, the capital of St. Barts, superyachts line the quay and the pace shifts to understated glamour. Waterfront tables at Bonito Saint Barth and Shellona offer polished dining with a distinctly international flair, while beach clubs hum from late afternoon into the evening. For those wishing to linger, Eden Rock - St Barths and Cheval Blanc St Barth Isle de France provide an elegant base, pairing beachfront settings with impeccable service.

Yet it’s the contrast that defines this itinerary. A short passage north brings you to the serenity of Anguilla, where long stretches of powder-white sand and clear, shallow waters invite a slower pace. At Blanchards and SALT, the culinary scene remains exceptional yet refreshingly relaxed, perfectly suited to languid lunches or understated evenings ashore. For overnight comfort, Four Seasons Resort and Residences Anguilla offers expansive views and easy access from nearby anchorages.

Balancing high-energy nightlife with genuine seclusion, this trio of islands creates a cruising ground where each short passage reveals a new mood, effortlessly shifting from chic sophistication to barefoot tranquillity, all within a few hours under way.

Favoured by seasoned cruisers, the Grenadines reward those willing to venture further south. From Bequia to Mustique and the Tobago Cays, this chain of islands offers some of the Caribbean’s most breathtaking anchorages and is ideal for longer stays and snorkelling. 

Each stop has its own distinct rhythm. In Bequia, a warm welcome awaits with its easy-going harbour, waterfront cafés and strong seafaring heritage. Further south, the exclusivity of Mustique brings a touch of understated glamour, where elegant villas and refined dining sit quietly behind swaying palms. For those seeking the quintessential castaway experience, the protected waters of the Tobago Cays deliver in full, think luminous shallows, thriving coral reefs and turtles gliding beneath the hull.

Ashore, the culinary scene remains authentic and deeply rooted in place. Beachfront institutions such as Jack's Beach Bar offer relaxed, toes-in-the-sand dining, while simple, locally run spots across the islands serve freshly caught seafood with little more than a grill and a view. For a more elevated experience, Bequia Beach Hotel provides boutique charm and a refined yet unfussy atmosphere, ideal for a night off the boat.

Exploring the Caribbean by yacht transforms the journey into part of the adventure, time to be enjoyed in its own right. With the freedom to pause where it suits, avoid the busiest anchorages, and linger longer in the places you love, each passage adds as much to the experience as the destinations themselves.

It’s a quiet kind of luxury, defined by space, privacy, and the ability to shape each day as it unfolds. With the right yacht, distances feel effortless and the practicalities fall away, leaving more time to focus on the places, the people, and the moments that make each trip memorable. 

When you’re ready to begin your next journey, speak to your Princess representative.