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Caribbean beaches, vibrant tropical fish, and savory West Indies cuisine during this 19-day transatlantic crossing. Relax, unwind and refocus with back-to-back spa days throughout your ocean crossing and dine on award-winning meals paired with the company of your new Windstar family. Relive history while sailing aboard a former America’s Cup competition sailboat or cook up delicious French meals with a certified chef in Grand Case outside Philipsburg, St. Maarten. Roll out in offroad vehicles for an unrushed day of snorkeling and relaxing on Tortola’s secluded beaches. Swim and frolic with dolphins near Jost Van Dyke in the British Virgin Islands. Snorkel above colorful coral and dizzying schools of curious fish prior to your private beach barbeque on Virgin Gorda in the British Virgin Islands. Glide over a sunken ship in a semi-submersible and take in a glowing Caribbean sunset during a catamaran cruise off Gustavia’s tropical beaches on St. Barts.
| Date | Country | Port | |
|---|---|---|---|
| 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 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 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 15 | 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 | 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 16 | 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 16 | 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 17 | 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 17 | 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 | Guadeloupe | Deshaies | |
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Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms. |
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| Day 19 | Guadeloupe | Deshaies | |
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Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms. |
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| Day 20 | Anguilla | Road Bay | |
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With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby. |
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| Day 20 | Anguilla | Road Bay | |
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With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby. |
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| Day 21 | British Virgin Islands | Sopers Hole, Tortola | |
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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 21 | British Virgin Islands | Sopers Hole, Tortola | |
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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 21 | 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 21 | 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 | 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 | 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 24 | 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 24 | 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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