Caribbean Island Hopping by Luxury Yacht — 10 Days Ultimate Archipelago Experience

Tour Overview

Itinerary Highlights

Day 1: Arrival in St. Martin — Embarkation & Sunset Cruise

Arrive at Princess Juliana International Airport on St. Martin, where the famous Maho Beach delivers the spectacle of aircraft landing just meters overhead — one of the most thrilling aviation experiences in the world. Your private driver transfers you to Simpson Bay Marina, where your home for the next week awaits: a 65-foot luxury motor yacht with a crew of three (captain, chef, and steward). After a Champagne welcome and safety briefing, settle into your en-suite cabin with panoramic views of the Simpson Bay Lagoon. Your captain provides an overview of the journey ahead — the islands you’ll visit, the passages you’ll sail, and the hidden gems only accessible by private yacht. As the Dutch-side drawbridge opens for its scheduled passage, your yacht glides out of the lagoon and into the Caribbean Sea. The first sunset from the deck of your yacht — Champagne in hand as St. Martin’s coastline recedes and the open sea stretches before you — sets the tone for the extraordinary days ahead. Your chef serves the first of many gourmet dinners: fresh-caught Caribbean lobster with mango salsa, coconut rice, and a chilled Sancerre, enjoyed in the open-air dining salon. Overnight at anchorage off St. Martin’s western coast near Marigot Bay, with only the gentle rock of the sea and the twinkle of shore lights for company.

Day 2: Anguilla — Road Bay, Sandy Ground & Shoal Bay

Wake to fresh coffee, tropical fruits, and pastries as your yacht cruises the short passage to Anguilla — just 30 minutes sailing brings you to the first island of your journey. Enter Road Bay and drop anchor in the protected waters of Sandy Ground, a lively beach village with colorful fishing boats bobbing in the harbor. Tender ashore to walk Road Bay’s white-sand beach and visit the boutiques, art galleries, and beach bars of this charming settlement. Your captain then skippers along Anguilla’s northern coast to anchor off Shoal Bay East — the legendary 2-mile beach voted among the world’s best by every major travel publication. Spend the afternoon snorkeling the reef that runs parallel to the shore, where visibility is extraordinary and the coral gardens teem with tropical fish. Tender to shore for lunch at a beachside grill serving grilled lobster and cold Carib beer with your toes in the sand. In the late afternoon, your yacht repositions to Crocus Bay, a peaceful anchorage on the western coast where the water is calm and the setting sun turns the limestone cliffs to gold. After dinner prepared by your chef, take the tender into the darkness — anglers among you might try for tarpon that hunt in the waters around the yacht, attracted by the underwater lights. Overnight at anchor in the serene bay, with the silhouette of St. Martin on the southern horizon.

Day 3: Prickly Pear & Sandy Island — Anguilla’s Offshore Paradise

Today ventures to Anguilla’s farthest reaches: set sail northward to the Prickly Pear Cays, uninhabited islands 8 miles northwest of Anguilla sitting atop one of the Caribbean’s most pristine reef systems. As your yacht approaches, the water transforms to impossible shades of aquamarine — the depth drops from the abyss of the open sea to a sun-drenched sandy bottom just 5 meters below your hull. This is snorkeling at its most spectacular: vast elkhorn coral gardens, schools of blue tangs and French angelfish, and frequent sightings of hawksbill turtles grazing on seagrass. Your chef prepares a beach barbecue — this is the Robinson Crusoe lunch you’ve always imagined: fresh fish or lobster grilled over charcoal on a deserted beach with only your party, your crew, and the seabirds for company. Wine, cold beer, and tropical cocktails flow as you alternate between swimming, snorkeling, and simply lying in the shallows watching the horizon. Mid-afternoon, cruise south to Sandy Island, an even smaller sandbar where a single rustic restaurant stands alone — at low tide, the sandbar extends far into the sea, creating the illusion of walking on water. Wade ashore for a rum punch at the tiny bar, collect sand dollars from the seabed, and photograph this ephemeral landscape that shifts and changes with every tide. As the sun begins its descent, your yacht makes the 90-minute passage south toward St. Barths. Night navigation along the coast of St. Martin with a sky full of stars and the distant glow of the French-speaking island lighting the horizon. Arrive at St. Barths anchorage in the quiet hours of the night. Overnight at anchor at Anse de Colombier, the most beautiful and exclusive bay on St. Barths.

Day 4: St. Barths — Colombier Bay, Gustavia & French Caribbean Glamour

Wake up in one of the Caribbean’s most beautiful anchorages: Colombier Bay on St. Barths’ northwestern coast, accessible only by boat or a 30-minute hiking trail — meaning you’ll have this pristine bay largely to yourself. The morning is pure pleasure: swim from the yacht’s swim platform in crystal-clear water, kayak into the sea caves that pocket the limestone cliffs, and snorkel the bay’s rich marine ecosystem. The crew serves a classic French breakfast — fresh croissants, baguette, French butter, seasonal fruits, and espresso — on the aft deck as the morning sun lights up the green hills of St. Barths. Late morning, cruise the dramatic north coast of the island past the surfing waves of Anse des Cayes and the exclusive enclave of St. Jean. Enter Gustavia harbor, where your yacht takes its place among the superyachts lining the quay — names like Eclipse, Musashi, and Seven Seas frequently grace these waters. Afternoon ashore in Gustavia: wander the streets lined with Hermès, Cartier, Louis Vuitton, and Prada; visit Shell Beach for sunset photos with the yachts as backdrop; and enjoy a cocktail at Le Select, the legendary bar where Jimmy Buffett and Johnny Depp have propped up the counter. Your chef has the evening off while you dine ashore at Bonito, one of St. Barths’ finest restaurants — the ceviche tasting menu and French-Latin fusion cuisine paired with views over the illuminated harbor is the definitive Gustavia dining experience. Return to your yacht for a nightcap on deck, watching the harbor lights shimmer on the water. Overnight at Gustavia marina.

Day 5: St. Barths — Full Day at Sea & Gouverneur Beach

A final St. Barths day dedicated to the south coast. After a leisurely breakfast, set sail around the southern tip of the island, passing the wild, undeveloped coast of Grand Fond where the Atlantic surf pounds the volcanic shore. Circle past Saline Beach, visible from the sea as a sweep of white sand backed by green dunes, and anchor off Gouverneur Beach — a stunning, secluded crescent frequently voted St. Barths’ most beautiful beach. Tender ashore for a few hours of swimming in the turquoise water of this uncrowded paradise, where the sand is so fine it’s like walking through powdered sugar. On board, your chef serves a gourmet lunch featuring the finest French-Caribbean fusion: a tower of fresh seafood, tropical fruit platters, fine cheeses, and chilled rosé. Mid-afternoon, the yacht lifts anchor for the longer passage south to St. Kitts. This 4-5 hour sail takes you through open Caribbean waters, with the silhouette of Statia (St. Eustatius) visible to port. This is the essence of yacht life — the rhythmic sound of the hull cutting through the sea, the trade winds in the rigging, the crew pointing out flying fish skimming across the waves, and the anticipation of the next island appearing on the horizon. As sunset approaches, Nevis Peak becomes visible — the perfect volcanic cone rising from a flat sea, a sight that has welcomed sailors to these islands for centuries. Dinner is served as you cruise past the southern coast of St. Kitts. Arrive at a calm anchorage off the Southeast Peninsula of St. Kitts, with the lights of Basseterre twinkling in the distance. Overnight at anchor with both St. Kitts and Nevis visible from the deck.

Day 6: St. Kitts — Brimstone Hill, Railway & Nevis Passage

After a floating breakfast served on the foredeck — the crew unfurls a floating water mat for the morning swim — disembark at Port Zante in Basseterre for your St. Kitts day. Your private driver and guide take you first to Brimstone Hill Fortress, the “Gibraltar of the West Indies.” The 30-minute drive through cane fields and villages leads to this astonishing UNESCO World Heritage site, where you’ll climb the bastions to stand where British cannons once commanded the Caribbean. The panoramic view from the citadel takes in six islands on a clear day, and the sight of your yacht — visible as a white speck in the sea far below — gives a new perspective on the scale of the Caribbean. After the fortress, experience the St. Kitts Scenic Railway, the Caribbean’s only working railway circling the island’s northeastern coast with onboard choir singing and rum punches. Lunch ashore at a local restaurant serving Kittitian specialties. Reboard your yacht at Port Zante for the short and delightful passage across The Narrows to Nevis, just 3 kilometers distant but a world apart in atmosphere. Anchor off Pinney’s Beach, the magnificent 3-mile stretch of golden sand with Nevis Peak as its backdrop. This evening is a special one: your yacht anchors close to shore, and you tender in for dinner at Sunshine’s Beach Bar — the “Killer Bee” rum punch is legendary, and the grilled lobster on this most beautiful of beaches is the very definition of luxury simplicity. Photo of the yacht from the beach, its lights reflected in the water with the volcano behind. Return to the yacht for a nightcap under the stars. Overnight at anchor off Pinney’s Beach.

Day 7: Nevis — Plantation Heritage & Resort Indulgence

After breakfast aboard, take the tender to shore for your Nevis exploration. Visit Charlestown, the island’s beautifully preserved Georgian capital, and the Alexander Hamilton Museum at the founding father’s birthplace. Walk through the town’s pastel-colored streets, visiting the Jewish Cemetery and the Bath Hotel thermal springs. Continue to the Golden Rock Inn, a 200-year-old sugar plantation transformed into a boutique hotel with extraordinary botanical gardens — the spring-fed reflection pool surrounded by tropical planting is one of the most photogenic spots in the Caribbean. Your guide shares Nevis’s plantation history, the story of sugar cultivation, and the legacy of the enslaved Africans who built this island economy. For a complete change of pace, the afternoon transitions to the Four Seasons Resort Nevis, where you check in for one night ashore — a welcome opportunity for a long hot shower, a spa treatment, and a resort dinner. Relax by the infinity pool overlooking Pinney’s Beach, enjoy the championship golf course if you play, or simply savor the luxury of a Four Seasons room with views of Nevis Peak. Dinner at Mango, the resort’s signature restaurant, featuring elevated Caribbean cuisine. Your yacht remains at anchor offshore — tomorrow you’ll resume the maritime journey with renewed appreciation for both sea and land. Overnight at Four Seasons Resort Nevis.

Day 8: Nevis Peak Hike & Sail to St. Martin Return

Morning hike on the lower slopes of Nevis Peak. Your guide leads a nature walk through the tropical rainforest on the volcano’s flank — the Saddle Trail offers spectacular views of both coasts without the technical demands of the summit ascent. Enormous tree ferns, wild orchids, and the calls of the green vervet monkeys create a Jurassic atmosphere. After the hike, return to the resort for a final Nevis swim at Pinney’s Beach. Check out and re-board the yacht, where your chef has prepared a farewell lunch for the island portion of your journey. The afternoon brings the longest passage of the trip: the sail back to St. Martin. This 5-6 hour voyage is the yacht’s finest moment — the seas are open and blue, the sun warm on deck, and the crew serves Champagne as the Leeward Islands slip past. Keep watch for dolphins, sea turtles, and even migrating humpback whales (January-April). This is the contemplative heart of the journey: the time to absorb everything you’ve experienced across four distinct island cultures, to watch the infinite variations of blue in the Caribbean Sea, and to understand why this particular mode of travel — by private yacht, at your own pace, with your own chef and crew — is the ultimate luxury experience. Arrive at St. Martin as the sun sets, anchoring in the calm waters off Marigot Bay on the French side. Farewell dinner prepared by your chef — a celebration of the islands you’ve visited: Anguillian lobster, St. Barths rosé, Nevisian mango and pepper sauce, and a flambéed dessert that creates a dramatic finale.

Day 9: St. Martin — French Culinary Scene & Maho Beach

Disembark your yacht mid-morning with a farewell to your captain and crew — the bond formed over a week at sea, navigating sunsets and snorkeling reefs together, is unique in travel. Transfer to La Samanna, a Belmond Hotel, or similar luxury resort on the French side of St. Martin for one final night on land. Your final full day explores the culinary riches of St. Martin/St. Maarten — the island widely regarded as the gastronomic capital of the Caribbean. The French side is home to an extraordinary concentration of excellent restaurants, from casual beachside “lolos” (local BBQ shacks) serving ribs, johnny cakes, and fresh fish, to elegant bistros rivaling those in mainland France. Visit the Marigot Market for tropical spices, local art, and the island’s famous guavaberry liqueur — the traditional Christmas drink of the Dutch side. Lunch at a beachfront restaurant in Grand Case, the “Gourmet Capital of the Caribbean,” where a single village street hosts more than 80 restaurants ranging from rustic to Michelin-recommended. The afternoon is yours: relax at the resort’s infinity pool overlooking the Caribbean, or head to Maho Beach for the legendary spectacle of aircraft landing just meters above the sand — a uniquely St. Maarten experience. Farewell dinner at a Grand Case fine dining restaurant, celebrating the completion of an extraordinary Caribbean odyssey that has taken you through five distinct island cultures, countless beaches, world-class snorkeling, and memories that will last a lifetime. Overnight at La Samanna or comparable luxury resort.

Day 10: Departure from St. Martin

Your final Caribbean morning. Enjoy a leisurely resort breakfast with views of the sea that has been your companion for the past ten days. Pack your bags — and pack some symbols of your journey: a bottle of guavaberry liqueur from St. Martin, Caribelle Batik fabric from St. Kitts, a vial of Montserrat volcanic ash (if you included the optional extension), French wines from the St. Barths cave à vin, and Anguillian sea salt. Your private driver transfers you to Princess Juliana International Airport. As your aircraft climbs over Maho Beach — watching thrill-seekers brace against the jet blast below — you’ll see the full sweep of the Leeward Islands stretched across the sea: Anguilla to the north, St. Barths and Saba to the southeast, St. Kitts and Nevis further to the south, and the island of St. Martin that has been your gateway to this extraordinary archipelago. You’ve experienced the Caribbean not as a single destination but as a constellation of cultures, flavors, and landscapes. Your tour concludes upon departure.

Included

• 7 nights aboard 65-foot luxury crewed motor yacht (4 en-suite cabins, captain, chef, and steward)
• 1 night at Four Seasons Resort Nevis (luxury room with volcano/ocean view)
• 1 night at La Samanna, A Belmond Hotel, St. Martin (or comparable 5-star resort)
• All meals and beverages aboard the yacht (gourmet chef-prepared breakfast, lunch, dinner daily)
• Curated wine, Champagne, and premium spirits throughout the yacht portion
• All fuel, port fees, marina docking fees, and cruising permits
• St. Barths Gustavia marina overnight docking (one of the Caribbean’s most expensive berths)
• Guided Brimstone Hill Fortress tour, St. Kitts (Day 6)
• St. Kitts Scenic Railway tickets (Day 6)
• Alexander Hamilton Museum and plantation heritage tour, Nevis (Day 7)
• Golden Rock Inn botanical gardens visit, Nevis (Day 7)
• Guided Nevis Peak rainforest nature walk (Day 8)
• All water toys: snorkeling equipment, kayaks, stand-up paddleboards, floating water mats, fishing gear
• Tender (dinghy) for all shore transfers
• St. Barths airport/villa transfer (Day 9 disembarkation)
• St. Martin airport transfers (arrival and departure)
• APA (Advance Provisioning Allowance) for all yacht expenses
• English-speaking captain who doubles as island guide throughout

Excluded

• International flights to/from St. Martin
• Crew gratuity (customarily 15-20% of charter fee, approximately $1,200-$1,800 per guest)
• Lunch on Day 6 (ashore on St. Kitts)
• Dinner on Day 4 (St. Barths — dining ashore at your choice of Gustavia restaurants)
• Shore excursions, taxis, and activities not specified in the itinerary
• Travel insurance (mandatory — must cover yacht charter and medical evacuation)
• Spa treatments at Four Seasons Nevis or La Samanna
• Off-yacht alcoholic beverages (except where specified at included dinners)
• Personal shopping, designer purchases, and souvenirs
• Customs and immigration fees (minimal — handled by captain)
• Optional Montserrat volcano extension (add 2 days / from $795 per person)

Why Choose This Tour

• Visit five Caribbean destinations — St. Martin, Anguilla, St. Barths, St. Kitts, and Nevis — in a single seamless journey, never unpacking more than once
• Private 65-foot crewed luxury yacht — your floating boutique hotel moving through the world’s most beautiful waters
• Gourmet chef preparing fresh, locally-sourced meals daily — Caribbean lobster, French-Caribbean fusion, and all dietary requirements accommodated
• Exclusive access to anchorages unreachable by land: Colombier Bay, Prickly Pear Cays, Pinney’s Beach waters
• Water toys included: snorkeling gear, kayaks, paddleboards, floating mats — explore every anchorage from the sea
• Perfect mix of yacht and land: 7 nights aboard, 2 nights at the Caribbean’s finest resorts (Four Seasons Nevis, La Samanna)
• Brimstone Hill Fortress, St. Kitts Scenic Railway, Gustavia shopping, Shoal Bay beach, Nevis Peak hiking — all major highlights included
• St. Barths overnight at Gustavia marina — watch your yacht take its place among the world’s most famous superyachts
• Crew of three dedicated entirely to your comfort — captain, chef, and steward ensure every moment exceeds expectations
• The ultimate multi-island Caribbean experience — only possible by private yacht, created for travelers who want to see the Caribbean at its very best