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This extended Atlantic-to-Caribbean sailing follows a rare winter route that links Europe, the open ocean, and the islands of the eastern Caribbean in one continuous journey, with experiences shaped by both destination and time at sea. Begin in Lisbon with its historic neighborhoods and riverfront cafés, then pause in Madeira for botanical gardens, coastal walks, and views from Monte. A true transoceanic crossing follows, offering days to settle into shipboard life before landfall in the Caribbean. Once there, small-ship access opens the door to snorkeling off Jost Van Dyke, beach time at Virgin Gorda’s Prickly Pear, exploring colonial streets in San Juan, and dining ashore in Gustavia after sunset. Cruz Bay and Basseterre invite hiking, sailing, and easy island exploration, creating a journey defined by variety, distance, and unhurried discovery.
| Date | Country | Port | |
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| Day 1 | Portugal | Lisbon | |
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The rhythm of Lisbon invites you to join its captivating dance. This splendid capital city on the banks of the Rio Teja offers a warm welcome and an unparalleled blend of architectural styles. Elegant outdoor cafés line the cobbled sidewalks. Turn-of-the-century funiculars climb the scenic hills. Find the UNESCO sites of the Tower of Belem and the Monastery of the Hieronymites. And, everywhere, the city engages you with its easy style and remarkable charm. |
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| Day 4 | Portugal | Funchal, Madeira | |
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Considered one of Portugal's main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty. Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there'll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life. |
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| Day 14 | British Virgin Islands | Great Harbour, Jost Van Dyke | |
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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 15 | Puerto Rico | San Juan (Puerto Rico) | |
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The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan. |
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| Day 17 | Saint Kitts and Nevis | Basseterre, Saint Kitts | |
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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 18 | Saint Barthélemy | Gustavia | |
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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 19 | Sint Maarten (Dutch part) | Philipsburg | |
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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 20 | British Virgin Islands | Great Harbour, Jost Van Dyke | |
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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 22 | Puerto Rico | San Juan (Puerto Rico) | |
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The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan. |
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