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Escape on an extraordinary tropical vacation on this twelve-day cruise to hidden harbors and secluded beaches throughout the Lesser Antilles in the Caribbean. Board a catamaran bound for Norman Island off Tortola and listen to pirate legends and treasure tales prior to your secluded snorkeling excursion among pristine reefs and tropical fish. Set a course in your own rigid inflatable boat (RIB) across bays and inlets near Jost Van Dyke before hopping off for swimming and snorkeling near Great Harbour’s scenic coastline. Cast deep lines for tuna, mahi-mahi, barracudas, and other delicious blue-water trophies off Nevis. Sample the sweetest of amber island ingredients in the thoughtful company of eco-minded beekeepers on St. Lucia. Admire sweeping harbor views as you sip local island rum with sweet cakes on a tasting tour of Fort Napoleon above Les Saintes. Sip Dominica’s Sea Moss non-alcoholic seaweed drink. Indulge your senses in classic Cuban cigars paired with spirits, wines, and cocktails at Basseterre, on St. Kitts.
Date | Country | Port | |
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Day 1 | Sint Maarten (Dutch part) | Philipsburg | |
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience. |
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Day 2 | British Virgin Islands | Sopers Hole, Tortola | |
Arrive at the boardwalk of Pusser's Landing and mingle with other yachtsmen in the utterly charming marina at Soper's Hole. Find a deserted stretch of beach to kick back and ponder this tiny port's rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away. |
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Day 2 | British Virgin Islands | Great Harbour, Jost Van Dyke | |
For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor. |
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Day 3 | British Virgin Islands | Great Harbour, Jost Van Dyke | |
For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor. |
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Day 5 | Saint Barthélemy | Gustavia | |
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by. |
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Day 6 | Sint Maarten (Dutch part) | Philipsburg | |
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience. |
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Day 8 | Dominica | Roseau | |
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you're up for an optional hike, don't miss Boiling Lake and the Valley of Desolation at Dominica's Morne Trois Pitons National Park, a UNESCO World Heritage Site. |
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Day 9 | Saint Vincent and the Grenadines | Mayreau Island | |
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform. |
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Day 10 | Guadeloupe | Terre-de-Haut | |
This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters. |
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Day 11 | Saint Kitts and Nevis | Basseterre, Saint Kitts | |
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site. |
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Day 12 | Saint Barthélemy | Gustavia | |
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by. |
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Day 13 | Sint Maarten (Dutch part) | Philipsburg | |
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience. |
Departing | Arrives | Price per person | |
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2nd December 2025 from Philipsburg | 14th December 2025 into Philipsburg | from £ 2,845pp |