Caribbean Yachting Retreats

The island’s diverse environment truly makes St. Maarten a marvel, as it is home to over 100 nationalities who speak more than 80 languages. The Dutch capital, Philipsburg, attracts visitors with its many art galleries, zoo and casinos. Soft white sands against serene blue waters make Great Bay Beach a perfect paradise to lie back and relax or go jet skiing and snorkeling. Shop for jewelry, clothing, electronics and perfume, all duty-free, along Philipsburg’s famous Front Street. The Sint Maarten Museum can be found on this street too, rife with the country’s history dating as far back as the Arawaks, the indigenous people of the Caribbean and South America.

The capital of the French St. Martin, Marigot, holds a quaint charm that can only be accessed by smaller ships, leaving it largely untouched by crowds and making room for local boutique shops and restaurants to flourish along its streets. From Marina Port La Royale you have plenty of restaurants to choose from along with a view of the yachts. In the Marigot Market you’ll find Bistro Nu, serving an inspiring menu that combines French and Créole cuisine. Overlooking the lagoon town is Fort Louis, the remains of a French castle atop a hill that give way to magnificent views.

The capital of the French St. Martin, Marigot, holds a quaint charm that can only be accessed by smaller ships, leaving it largely untouched by crowds and making room for local boutique shops and restaurants to flourish along its streets. From Marina Port La Royale you have plenty of restaurants to choose from along with a view of the yachts. In the Marigot Market you’ll find Bistro Nu, serving an inspiring menu that combines French and Créole cuisine. Overlooking the lagoon town is Fort Louis, the remains of a French castle atop a hill that give way to magnificent views.

White, sandy beach shores, azure waters and palm trees on the horizon make Anguilla an absolute paradise. Rendezvous Bay Beach is a popular destination for a relaxing beach day with comfortable amenities. Stop by the renowned Elvis’ Beach Bar in Sandy Ground to sample their famous rum punch. Walk along the main beach to take in the electric energy of dozens of restaurants and a bustling harbor. For quieter adventures, head to Sandy Island and enjoy a day of snorkeling and other water sports away from the crowds. Or venture a little further inland toward North Hill Village to satisfy your appetite at a local restaurant. Find your way to the Pamead shipwreck for an exciting adventure that sparks the imagination.

A world apart from its mountainous neighbors, Anegada is the only coral island in the British Virgin Islands—an unspoiled escape known for its powdery white-sand beaches and tranquil turquoise waters. Secluded and serene, it offers a barefoot adventure for those seeking quietude or a taste of the wild. Embark on a 4x4 safari across the island’s flat terrain to spot pink flamingos wading in salt ponds or discover the hidden beauty of Loblolly Bay, where colorful coral reefs lie just offshore, perfect for snorkeling. After a day of exploring, unwind with grilled lobster and a rum punch at one of the island’s rustic beach bars, where time seems to slow and island rhythms take over.

White Bay on Jost van Dyke is a stunning beach destination in the British Virgin Islands renowned for its crystal-clear turquoise waters and powdery white sand. Famous for the iconic Soggy Dollar Bar, where the legendary Painkiller cocktail was born, this laid-back hideaway also invites visitors to relax at Hendo’s Hideout, a beloved beachfront bar with a vibrant island vibe. Whether you’re soaking up the sun, snorkeling, or enjoying local flavors, White Bay offers an unforgettable Caribbean escape.

With its laid-back charm and barefoot vibe, Great Harbour on Jost Van Dyke captures the essence of island living in the British Virgin Islands. This tiny, carefree port is best known for its iconic beach bars—most famously Foxy’s, where travelers and locals mingle over legendary cocktails, fresh seafood, and live island music. Beyond the festivities, white-sand beaches and calm, clear waters invite you to swim, snorkel, or simply soak in the tropical sunshine. Whether you’re here to raise a glass or relax beneath swaying palms, Great Harbour offers a slice of paradise that feels worlds away from the everyday.

Virgin Gorda, part of the British Virgin Islands, is renowned for its natural beauty. Spanish Town, also known as The Valley, is the second-largest city among these islands, the heart of which is the Yacht Harbor marina. Stroll along its dock for prime shopping and watch the boats as they sail in and out of port. Stop in at one of the local restaurants for a quick snack before exploring the town and becoming acquainted with the residents.

With its golden sands stretching for miles against the backdrop of lush Nevis Peak, Pinney’s Beach is the island’s crown jewel—a picture-perfect escape where serenity meets barefoot luxury. Stroll the soft shoreline, swim in the calm Caribbean waters, or sip a signature rum punch at a chic beach bar like the famed Sunshine’s. Just beyond the palms, Nevis reveals its quiet charm, from historic plantation inns to botanical gardens and warm island hospitality. Whether you’re seeking total relaxation or a touch of tropical sophistication, Pinney’s Beach offers an unforgettable taste of Nevisian paradise.

St. Barts, an island within the archipelago of the French West Indies, contains deep valleys, stunning beaches and verdant, formerly active volcanic hills. Within all this sits the capital city of Gustavia with a diverse cultural heritage on display through Swedish colonial and French Creole architecture most easily seen in its signature red-roofed buildings. The beaches are the main attraction, offering unspoiled coves such as Gouverneur and quiet scenes like Saline for more intimate beach days. For a more active adventure, do the Colombier hike that leads you to the perfect snorkeling spot. Savor the exquisite flavors of Cajun and Creole seafood and staples like conch gratin, minced beef and the island specialty – banana flambé.

St. Barts, an island within the archipelago of the French West Indies, contains deep valleys, stunning beaches and verdant, formerly active volcanic hills. Within all this sits the capital city of Gustavia with a diverse cultural heritage on display through Swedish colonial and French Creole architecture most easily seen in its signature red-roofed buildings. The beaches are the main attraction, offering unspoiled coves such as Gouverneur and quiet scenes like Saline for more intimate beach days. For a more active adventure, do the Colombier hike that leads you to the perfect snorkeling spot. Savor the exquisite flavors of Cajun and Creole seafood and staples like conch gratin, minced beef and the island specialty – banana flambé.

Vibrant and welcoming, St. John’s is the colorful capital of Antigua where colonial charm meets island energy. Wander through lively streets lined with pastel-hued buildings, bustling markets, and duty-free shops offering local crafts and luxury goods. History comes alive at nearby Fort James and Fort Barrington, where panoramic views and echoes of the island’s past await. For golf enthusiasts, tee off at the scenic Cedar Valley Golf Club, where tropical breezes and lush fairways offer a picturesque challenge. Whether you’re exploring historic sites or savoring Caribbean flavors by the harbor, St. John’s captures the spirited heart of Antigua.