St. Barts & Beyond: 7 Days of Caribbean Sailing

A gateway into the dual-identity island of St. Martin/St. Maarten, Marigot blends French-Caribbean charm with European sophistication. The town itself offers a lively mix of colorful colonial architecture, waterfront cafés, and local markets ideal for provisioning or simply soaking up island culture. Beyond its streets, the island reveals its two souls—French elegance to the north and Dutch vibrance to the south. For sailors, the fully serviced marinas in nearby Simpson Bay and the expansive Simpson Bay Lagoon (12 square miles of protected waters) are a hub of international yachting activity, often dotted with spectacular superyachts. Visitors flock here each year not only for the stunning beaches and snorkeling-friendly marine parks, but also for major sailing events like the Heineken Regatta and the Classic Yacht Regatta. Whether you're here to set sail, shop duty-free, or dine in one of the island’s hundreds of restaurants, Marigot invites you to experience the heart of the Caribbean with flair and flavor.

Located on the northeast coast of French St. Martin, Orient Bay is one of the most vibrant and versatile stops on a northern Leeward Islands sailing itinerary. Its wide arc of white sand, consistent trade winds, and lively waterfront make it a haven for watersports like kite surfing, windsurfing, and kayaking. Beyond the action, Orient Bay also offers relaxed anchorages for those seeking peace amid scenic surroundings. Ashore, you'll find an enticing mix of restaurants, boutiques, and beach bars with both family-friendly and adult-only sections—including areas like Green Cay, known for nude sunbathing. Just offshore, Île Pinel offers a more secluded vibe with rustic beach shacks, water sports rentals, and panoramic views from above for those adventurous enough to take a ride in an ultralight aircraft. Though approach conditions require caution, Orient Bay rewards sailors with the perfect blend of energy and escape.

Often referred to as the “Riviera of the Caribbean,” Gustavia is the elegant heart of St. Barts and a must-visit port on any Eastern Caribbean yacht charter. Nestled between emerald hills and the sparkling sea, this chic harbor town welcomes sailors with a well-protected anchorage, world-class marina facilities, and a captivating blend of French sophistication and tropical charm. Stroll through its cobblestone streets lined with red-roofed buildings, where luxury boutiques, art galleries, and exquisite French restaurants invite indulgence at every turn. The town’s laid-back yet refined energy makes it a favorite among superyacht owners and cruising sailors alike. For a change of pace, a short hike to Fort Gustav rewards you with breathtaking panoramic views, while a trip to nearby Anse de Colombier offers serene swimming, sunbathing, and snorkeling in a protected marine reserve. Gustavia is not just a port—it’s a lifestyle experience.

Tucked away at the western tip of St. Barts, Anse de Colombier offers a postcard-perfect anchorage that feels like a well-kept secret of the Caribbean. This horseshoe-shaped bay, protected by steep hills and embraced by turquoise waters, is a favorite among seasoned cruisers for its tranquility, scenic beauty, and excellent snorkeling opportunities. Once the private retreat of the Rockefeller family, the area is now part of the St. Barts Marine Reserve and retains its unspoiled charm.

With no road access, the bay remains peaceful and crowd-free, reachable only by boat or hiking trail from nearby Anse de Flamandes. Underwater, snorkelers and divers can explore vibrant reefs and rocky coves teeming with marine life—look out for sea turtles and rays near the southern inlet. On land, a trail leads through wild lilies and cacti to panoramic viewpoints that offer breathtaking vistas of the bay and beyond. Yachting here is more than a stop—it's a serene escape into nature and island elegance.

Welcoming sailors with its laid-back charm and sparkling waters, Road Bay is the main port of entry to Anguilla and one of the finest anchorages in the northern Leewards. Its long stretch of white sand, dotted with easygoing beach bars and restaurants, offers the perfect introduction to the island’s serene, unpretentious spirit. Whether you're relaxing at Johnno’s to the sounds of weekend live music or enjoying a beachfront cocktail under the Caribbean sun, Road Bay is all about embracing island time.

Beyond the shore, Anguilla invites exploration. Rent a car and discover hidden coves, quiet roads, and the quaint capital, The Valley. Bird lovers will enjoy Caul’s Pond, while diving enthusiasts can explore the island’s legendary wreck dives—seven sunken ships transformed into colorful marine sanctuaries. From snorkeling at Prickly Pear Cays to unwinding on the protected shores of Crocus Bay, Anguilla delivers a sailing escape rich in nature, culture, and unforgettable coastal beauty.

Crocus Bay offers a tranquil anchorage surrounded by dramatic cliffs and a pristine white-sand beach—an inviting retreat for sailors seeking serenity. The clear waters are ideal for swimming and the nearby Pelican Point provides excellent snorkeling opportunities. Just a short sail away lies Little Bay, known for its vibrant cliffs and birdlife. Located within walking distance from Anguilla’s main town, The Valley, Crocus Bay is both peaceful and conveniently connected to island culture.