St. Barts & Beyond: 7 Days of Caribbean Sailing
Sail through the best of the Leeward Islands, from the elegance of St. Barts to the serenity of Anguilla.
Let the sea set you free—join us on this unforgettable Caribbean adventure!
From Chic Harbors to Secluded Coves
Embark on a dream sailing escape through the sun-drenched waters of the Leeward Islands, where French flair, Dutch charm, and Caribbean rhythm blend seamlessly. From vibrant harbor towns to secluded bays, each day promises a new horizon and a deeper connection with the sea.
Day 1: Marina Fort-Louis, Marigot (St. Martin)
Begin your journey at Marina Fort-Louis in Marigot, a bustling yet charming French-Caribbean port town. Take time to stock up on supplies, enjoy a café au lait, and explore the boutique-lined streets before boarding your yacht. Settle in for a relaxing evening at the marina and prepare for the adventure ahead.
Day 2: Marigot to Grand Case (St. Martin)
Sail north to the culinary capital of St. Martin—Grand Case. Drop anchor off the pristine beach and dinghy ashore to enjoy a gourmet dinner at one of the many French restaurants. The anchorage is calm, the sunsets are golden, and the atmosphere is laid-back yet refined.
Day 3: Grand Case to Anse de Colombier (St. Barts)
Set sail to the chic island of St. Barts and anchor in the horseshoe-shaped Anse de Colombier. This tranquil bay, only accessible by sea or hiking trail, offers clear waters for snorkeling and a peaceful anchorage surrounded by rolling green hills. It's the perfect place to unwind in paradise.
Day 4: Anse de Colombier to Gustavia (St. Barts)
Cruise around to Gustavia, the elegant capital of St. Barts. Dock or anchor just outside the harbor and explore this cosmopolitan hub known for its designer shops, French cafés, and vibrant yachting scene. A sunset cocktail here feels straight out of the Riviera.
Day 5: Gustavia to Great Bay, Philipsburg (St. Maarten)
Sail west back toward Dutch St. Maarten and anchor in Great Bay near Philipsburg. Enjoy a lively mix of beach bars, shopping, and nightlife. For a change of pace, visit the St. Maarten Museum or stroll the boardwalk that stretches along the shore.
Day 6: Philipsburg to Road Bay (Anguilla)
Set course for the British island of Anguilla and anchor in Road Bay. Known for its relaxed vibe and friendly locals, this port offers access to white-sand beaches, beach bars with live music, and the possibility of renting a car to explore the island’s hidden gems.
Day 7: Road Bay – Crocus Bay – Marina Fort-Louis (St. Martin)
Enjoy a peaceful morning with a short sail or dinghy ride to Crocus Bay, a serene cove known for its golden cliffs and calm waters—ideal for a final swim or quiet reflection. After soaking in Anguilla’s natural beauty one last time, set sail back to Marina Fort-Louis in Marigot. As you return your yacht, take a moment to savor the memories of a week filled with island elegance, vibrant culture, and open-sea freedom.
Marigot – St. Martin
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.
Simpson Bay is a lively coastal hub known for its calm lagoon, sailing activity, and vibrant marina life. Popular among yacht enthusiasts, the bay offers calm anchorage and easy access to marine services. Beyond the water, visitors can enjoy a range of restaurants, bars, and casinos, making it a well-rounded destination for both relaxation and entertainment. The sunset views from anchored boats are a true highlight, creating a perfect end to an adventurous day at sea.
Located in the heart of Marigot, Marina Fort Louis is one of the most picturesque marinas in the Caribbean. Surrounded by charming cafes and boutique shops, this marina blends European flair with Caribbean warmth. Its proximity to the historic Fort Louis adds a cultural touch, offering visitors the opportunity to explore the past while enjoying modern comforts. It’s the ideal spot to dock, dine, and discover.
Hidden behind a short trail through the forest, Happy Bay Beach is one of St. Martin’s most serene and untouched beaches. Its soft golden sand and turquoise waters create a postcard-perfect setting ideal for swimming, sunbathing, and peaceful strolls. The secluded atmosphere makes it a favorite for those seeking tranquility away from the more crowded beaches of the island. Bring a picnic and enjoy a day in pure Caribbean bliss.
Orient Bay – French St. Martin
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.
Green Cay is a small, uninhabited islet off the northeast coast of St. Martin, beloved for its natural beauty and pristine marine environment. Surrounded by shallow turquoise waters and vibrant coral reefs, the cay is a dream spot for snorkeling enthusiasts. Sea turtles and colorful tropical fish glide effortlessly through the water, offering a peaceful escape into the underwater world. Accessible by boat or kayak, Green Cay is ideal for those seeking serenity and connection with nature just a short sail from the mainland.
Coco Beach is where elegance meets the shore. Set on the golden sands of Orient Bay, this stylish beach club invites you to bask under the Caribbean sun with a chilled cocktail in hand. Whether you’re lounging on a premium sunbed or enjoying a vibrant seafood lunch with your toes in the sand, Coco Beach offers a blend of sophistication and island charm. A favorite among yacht travelers, it’s the perfect place to unwind after a morning sail.
Chic, trendy, and unmistakably Caribbean—Kontiki Beach is a must-visit for boaters. With its white canopies, elegant lounge beds, and refined cuisine, this beach club blends barefoot luxury with tropical ambiance. The vibe is relaxed during the day and stylishly energetic by sunset. It's a hotspot for those who enjoy both relaxation and a touch of glamour during their sailing journey.
Located in Orient Bay Village, L’Atelier is a French-style steakhouse that combines casual elegance with gourmet flair. Known for its prime cuts like USDA Prime Black Angus, Japanese and Australian Wagyu, Iberico pork, and local fish, the menu also includes vegetarian options and expertly crafted cocktails. The cozy atmosphere, attentive service, and warm ambiance make it a standout spot for a refined evening in paradise. Many guests rave that the steaks “are amazing” and the fish dishes equally impressed .
A local favorite, Yellow Sub is a laid-back beachside sports bar and grill right on Orient Bay Beach. Open daily from early morning to late afternoon, it offers hearty breakfasts, casual lunches, and vibrant dinner and party vibes. Known for big juicy burgers, rotisserie chicken, and local breweries on tap, Yellow Sub is also the go-to spot for watching live sports on multiple screens. With its friendly staff, reasonable prices, and occasional live music or karaoke, it captures the casual charm of island life.
Gustavia – St. Barts
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.
Nestled right on the soft sands of Shell Beach, Shellona is one of Gustavia’s most glamorous beach clubs, blending boho-luxury with Caribbean charm. With its iconic white parasols, stylish lounging, and fresh Mediterranean-inspired cuisine, this is the perfect place to unwind after a morning sail. Whether you're sipping rosé to the rhythm of a live DJ or diving into turquoise waters, Shellona captures the essence of effortless island sophistication.
Perched atop a hill overlooking the harbor, the Gustavia Lighthouse offers sweeping views over the yacht-filled bay and the sparkling Caribbean horizon. A short and scenic hike leads you to this serene spot—perfect for photo lovers and those seeking a quiet, panoramic moment of reflection.
A glamorous extension of the fashion house’s bold aesthetic, Martini Bar is where luxury meets nightlife in Gustavia. With chic décor, expertly crafted cocktails, and a crowd of international trendsetters, it's a must-visit for those who enjoy stylish evenings under the Caribbean stars.
Overlooking the harbor, BONITO is a refined blend of French elegance and Latin spirit. Known for its laid-back luxury and panoramic views, it offers fresh ceviches, grilled seafood, and an award-winning cocktail list in a warm, coastal ambiance.
Bringing the flavors of Italy to the heart of the Caribbean, L’Isola is a fine dining experience rooted in authenticity. Its intimate atmosphere, sophisticated service, and rich Italian dishes make it a timeless favorite among both locals and yacht travelers.
A local gem with a relaxed garden setting, Eddy’s Ghetto offers a true taste of Saint Barth through Creole-infused Caribbean cuisine. Its friendly, casual vibe and flavors that speak of island heritage make it a favorite for a laid-back yet authentic night out.
Anse de Colombier
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.
Great Bay-Dutch St. Maarten
Set your anchor in the vibrant heart of Dutch St. Maarten—Philipsburg, nestled along the sweeping shores of Great Bay. This bustling capital is a favorite stop for sailors, offering a unique mix of island charm and cosmopolitan flair. From well-equipped marinas to lively waterfront restaurants, high-end boutiques, and a lively casino scene, everything you need is within walking distance of the shore. Whether you're indulging in duty-free shopping, dining with a view of the bay, or simply soaking up the town's colorful energy, Philipsburg is where Caribbean adventure meets comfort. Don't miss the small yet insightful local museum for a glimpse into the island's rich history.
Stretching gracefully along the white sands of Great Bay, the Philipsburg Boardwalk is the beating heart of Dutch St. Maarten’s coastal life. This scenic promenade invites visitors to stroll by the sea, enjoy beachfront dining, browse souvenir shops, or simply pause to watch the waves roll in. From morning coffee to sunset cocktails, the Boardwalk offers a lively yet relaxed atmosphere where local culture, sea breeze, and island charm come together. A must-visit for those who love a blend of leisure, shopping, and sea views.
Tucked between the bustling Front Street and the beachside Boardwalk, Old Street is a hidden gem full of Caribbean character and charm. This narrow pedestrian lane, framed by colorful colonial-style buildings and vibrant murals, feels like stepping into a postcard. Lined with boutique shops, local art galleries, and cozy cafés, it’s a perfect spot for relaxed shopping and stunning photos. Whether you’re looking for handmade souvenirs or simply want to wander through a quiet, picturesque alley, Old Street offers a peaceful escape in the heart of Philipsburg.
Located within the elegant Holland House Hotel, Ocean Lounge offers a refined culinary journey paired with postcard-worthy ocean views. The menu features a fusion of international and Caribbean cuisine, artfully prepared and served in a stylish beachfront setting. Whether you're indulging in a romantic dinner or sipping sunset cocktails, Ocean Lounge provides a serene and sophisticated atmosphere.
Famous for its award-winning craft beer, Dutch Blonde Beach Bar is more than just a brewery—it's a beachfront hub for fun, food, and great vibes. Enjoy hearty burgers, fresh salads, and signature cocktails in a lively setting overlooking the sea. Don’t miss their in-house brewery and quirky charm that perfectly reflects the island’s playful spirit.
Road Bay
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.
Nature’s artistry shines at Anguilla Arch, a stunning coastal rock formation sculpted by time and tide. Set against the endless blue of the Caribbean Sea, this natural arch offers a breathtaking view and a favorite photo opportunity for adventurers and dreamers alike. It's a serene and humbling reminder of Anguilla’s raw, untouched beauty—perfect for those seeking peaceful moments and unforgettable scenery.
Perched on a rugged stretch of Anguilla’s coastline, Shipwreck is not just a scenic stop—it’s a feeling. Overlooking turquoise waters and softened by sea breezes, this hidden beachfront spot is where time slows down. Visitors come here to relax with a drink in hand, soak in coastal views, or enjoy live music in the evenings. Casual yet soulful, Shipwreck offers a raw, laid-back charm that makes you feel like you’ve stumbled upon a well-kept island secret.
Tucked right on the sandy edge of Road Bay, SandBar is a favorite for those who love sophisticated simplicity. The menu offers shareable small plates inspired by global flavors, paired with creative cocktails and sweeping sea views. Whether you're coming for sunset tapas or an intimate dinner by the water, SandBar blends casual elegance with culinary flair.
Johnno’s is a Road Bay classic—a laid-back beachfront institution where music, good food, and local culture come together. Famous for its live jazz sessions and grilled seafood, this open-air restaurant offers an authentic island experience. Come barefoot, stay for the vibe, and enjoy the rhythm of Anguilla at its most relaxed.
Elegant and refined, Dolce Vita offers a taste of Italy with a Caribbean twist. Overlooking the calm waters of Road Bay, the restaurant is known for its handmade pasta, fine wines, and attentive service. Perfect for a romantic evening or a special celebration, Dolce Vita turns every meal into a memorable event.
Crocus Bay
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.
Accessible only by boat or a steep descent, Little Bay is one of Anguilla’s best-kept secrets. Tucked between rugged cliffs, this small, secluded cove boasts crystal-clear waters and a peaceful atmosphere perfect for snorkeling, swimming, or simply floating in silence. It’s the kind of place that makes you feel like you’ve discovered your own private slice of paradise.
Tucked away on the remote northeastern coast of Anguilla, Pelican Point is a serene escape for nature lovers and solitude seekers. This untouched headland offers sweeping views of the Atlantic Ocean, dramatic cliffs, and the occasional sighting of pelicans gliding above the waves. With no crowds or noise, it’s the perfect place to breathe deeply, reflect, and reconnect with the raw beauty of the island.
Set along the tranquil Crocus Bay, Da'Vida blends Caribbean elegance with oceanfront dining at its finest. The menu showcases local seafood and island-inspired dishes prepared with a gourmet twist, all served in an open-air setting with panoramic sea views. Whether you're arriving by boat or car, Da'Vida is a celebration of Anguillan hospitality, where every meal feels like a special occasion.
Located within the exclusive Belmond Cap Juluca resort, Cip’s by Cipriani brings Venetian sophistication to the Caribbean. Overlooking the pristine Maundays Bay, this upscale restaurant features classic Italian cuisine with refined flavors and impeccable service. From handmade pasta to fine wines, every detail is crafted to perfection—ideal for romantic dinners and elegant evenings under the stars.
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