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Trace a route shaped by early explorers, coastal trade routes, and the natural beauty of the southern Caribbean. Visit San Juan, Santo Domingo, Cartagena, and Santa Marta—four of the New World’s oldest cities—then snorkel Isla Catalina’s well-known reef and the coral gardens of Les Saintes. An overnight in Cartagena lets you explore its walled quarters after the day-trippers leave. Farther south, rainforest hikes, calm anchorages, and island communities like Bequia and Les Saintes offer a more relaxed rhythm. Together, the journey brings historical context and Windstar-style access to a wide sweep of the Caribbean.
| Date | Country | Port | |
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| Day 1 | 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 3 | Grenada | Saint George's | |
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Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must. |
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| Day 4 | Saint Vincent and the Grenadines | Port Elizabeth, Bequia | |
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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 5 | Saint Vincent and the Grenadines | Mayreau Island | |
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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 6 | Guadeloupe | Terre-de-Haut | |
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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 7 | Saint Martin (French part) | Marigot | |
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Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's most prestigious brands can be found. Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay. |
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| Day 8 | 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 9 | Mexico | Isla Catalana | |
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Small Isla Catalina boasts gleaming white-sand beaches ringed by coral reefs beckoning snorkelers. The island is a protected Natural Park where one beach is completely protected from the wind and the sea is delightfully calm. While beaches occupy more than 2/3 of the coastline, Isla Catalina also has unique rocky coasts and cliffs. One of the best diving sites of the Dominican Republic, Muro, can be found here. It boasts an impressive underwater wall over 328 feet deep. Isla Catalina is also the only place in the D.R. where raccoons and wild hares can be found. |
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| Day 10 | Dominican Republic | Santo Domingo | |
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La Capital, as Santo Domingo is affectionately known, is a UNESCO site and one of the oldest cities in the Caribbean, with Zona Colonial buildings dating back to the 1500s. Santo Domingo is also considered the most modern metropolis in the Caribbean doing a great job of converging old and new. At the heart of the Zona Colonial, a pedestrian-friendly maze of cobblestones and interesting architecture is the first cathedral built in the New World. Find time to sample the aromatic coffee and cacao. |
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| Day 12 | Colombia | Cartagena | |
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Welcome to the sparkling city of Cartagena, where the gold and jewels of the Spanish Main awaited shipment across the Atlantic. No pirate could resist, nor will you be able to when you visit this historic city. The Old Town, a UNESCO World Heritage Site, is surrounded by 400-year-old walls and contains a plethora of churches, fortresses, and restored colonial mansions. Outside the walls are more treasures: Climb the massive Castillo de San Felipe to investigate its maze of hidden tunnels, or shop for the perfect emerald. |
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| Day 13 | Colombia | Cartagena | |
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Welcome to the sparkling city of Cartagena, where the gold and jewels of the Spanish Main awaited shipment across the Atlantic. No pirate could resist, nor will you be able to when you visit this historic city. The Old Town, a UNESCO World Heritage Site, is surrounded by 400-year-old walls and contains a plethora of churches, fortresses, and restored colonial mansions. Outside the walls are more treasures: Climb the massive Castillo de San Felipe to investigate its maze of hidden tunnels, or shop for the perfect emerald. |
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| Day 14 | Panama | San Blas Islands | |
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The San Blas Islands of Panama is an archipelago comprising approximately 378 islands and cays, of which 49 are inhabited, some by the Kuna people. Scattered over an area of about 100 square miles, the islands are the number 1 vacation destination in Panama although the Kuna work hard to protect their land against overwhelming tourism and keep the islands healthy and lovely, unique and untouched by culture. These white-sand and palm tree lined islands are encompassed by a coral reef and warm, crystal-clear water that is perfect for snorkeling and is home to a variety of marine life including dolphins, sharks and giant manta rays. |
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| Day 15 | Panama | Colón | |
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Explore the inner workings of the Panama Canal, head into the jungle to meet with Embera Indians, or take an aerial tram ride through the rainforest canopy. |
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