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Get acquainted with the Caribbean’s most iconic and little-known vacation destinations during this comprehensive and romantic 28-port, 20-country voyage to the Windward and Leeward Islands, Colombia, and a guided daylight transit of the Panama Canal. Zipline through the shady Antigua Rainforest near Falmouth Harbour. Savor deep-fried pastries filled with warm and tasty seafood on Bonaire. Board a semi-submersible bound for underwater marine parks and sunken ships off the shores of St. Barts. Master delicious Creole cuisine during a beachside cooking class with a local Martinique chef. Swim and snorkel prior to an overnight stay in Jost Van Dyke. Cook up decadent chocolate confections from locally grown cocoa nibs near Castries. See Cartagena’s colonial architecture from a classic horse-drawn carriage perspective. Relax during a narrated daylight transit of the Panama Canal as you uncover how early engineers overcame formidable and deadly challenges. Linger on deck on warm, moonlight nights with the gentle lapping of the water below and the sparkling plethora of stars above.
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 3 | Anguilla | Road Bay | |
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 4 | 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 5 | 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 6 | 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 7 | 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 8 | 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 9 | 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 10 | 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 12 | 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 13 | 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 14 | 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 15 | Barbados | Bridgetown | |
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave. |
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Day 17 | 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 19 | 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 20 | 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 21 | 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 22 | Martinique | Trois-Ilets | |
Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views. |
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Day 23 | Barbados | Bridgetown | |
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave. |
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Day 24 | Saint Vincent and the Grenadines | Tobago Cays | |
Sail, snorkel, or beachcomb in complete seclusion in this unspoiled tropical paradise accessible only by boat. Quiet coves like Horseshoe Reef are home to fantastic coral reefs, while nearby Baradel offers an excellent opportunity to observe the area's famous sea turtles. Crystalline waters and perfect weather make this an ideal spot to play in the sea |
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Day 25 | Saint Lucia | Pigeon Island | |
The UNESCO site Pitons' with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches. |
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Day 26 | Saint Lucia | Pigeon Island | |
The UNESCO site Pitons' with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches. |
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Day 26 | Saint Lucia | Castries | |
The capital and largest city of St. Lucia is a bustling port where shoppers flock. Most of the city's historic buildings were destroyed in major fires between 1785 and 1948 but you'll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor. Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square. |
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Day 27 | 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 28 | Saint Vincent and the Grenadines | Port Elizabeth, Bequia | |
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces. |
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Day 29 | Barbados | Bridgetown | |
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave. |