Cozumel
Cozumel 02/17/2026
The Mesamerican Barrier Reef spans 14 miles around the Mexican island of Cozumel and the impressive marine diversity here makes it an excellent place for snorkeling and diving. Chankanaab, an eco-park surrounding a lagoon offers underwater caverns that are home to dolphins, manatees and sea turtles. Or take a ferry ride over to the mainland to explore the beaches of Playa del Carmen.
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02/17/2026 |
02/17/2026 |
At Sea
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02/18/2026 |
02/18/2026 |
Grand Cayman (George Town)
Grand Cayman (George Town) 02/19/2026
The largest of the Cayman Islands, Grand Cayman is known for its beautiful beaches and coral reefs. Seven Mile Beach, for one is a long stretch of white sand, calm turquoise waters and shops and restaurants. Stingray City is the most popular attraction where the stingrays can be touched, fed and even held. The island has one cross-country walking path, the Mastic Trail and horseback riding on the beach may be the best way to experience the beauty of this place.
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02/19/2026 |
02/19/2026 |
Cayman Brac
Cayman Brac 02/20/2026
On tiny Cayman Brac, The Bluff, a limestone cliff running the length of the island contains numerous caves including the Bat Cave. It is a nature lover’s dream of lovely secluded beaches and lush green forests. Birdwatchers can search for endangered parrots, brown boobies and peregrine falcons or see the parrots at the Parrot Reserve. The hiking trails that crisscross the island lead to historic sites, reptilian habitats and unusual flora.
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02/20/2026 |
02/20/2026 |
Port Antonio
Port Antonio 02/21/2026
Known as the gateway to the nearby Reach Falls, with its series of cascades tumbling from pool to pool, John Crow Mountains and tropical jungles, Port Antonio is a delightful hodgepodge of markets, street vendors, greenery, beaches and Georgian architecture. Experience the fun of taking a bamboo raft down the Rio River and don’t miss the world famous bottomless Blue Lagoon.
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02/21/2026 |
02/21/2026 |
At Sea
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02/22/2026 |
02/22/2026 |
Santo Domingo
Santo Domingo 02/23/2026
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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02/23/2026 |
02/23/2026 |
Casa de Campo
Casa de Campo 02/24/2026
La Romana has something for every outdoor lover. White-sand beaches, pristine coral reefs, shallow and extreme depth waters teeming with marine life, fields of sugar cane, and cave-riddled forests where Taino rock art and fresh-water springs can be found. It is also home to the renowned Casa de Campo Resort with its award-winning golf course and 16th century Altos de Chavon, an amazing replica of a Mediterranean village.
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02/24/2026 |
02/24/2026 |
At Sea
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02/25/2026 |
02/25/2026 |
Jost Van Dyke
Jost Van Dyke 02/26/2026
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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02/26/2026 |
02/26/2026 |
Virgin Gorda
Virgin Gorda 02/27/2026
The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns
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02/27/2026 |
02/27/2026 |
St. Maarten (Philipsburg)
St. Maarten (Philipsburg) 02/28/2026
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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02/28/2026 |
02/28/2026 |
Charlestown
Charlestown 03/01/2026
This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney’s Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.
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03/01/2026 |
03/01/2026 |
Roseau, Dominica
Roseau, Dominica 03/02/2026
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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03/02/2026 |
03/02/2026 |
Pigeon Island, St. Lucia
Pigeon Island, St. Lucia 03/03/2026
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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03/03/2026 |
03/03/2026 |
Iles des Saintes
Iles des Saintes 03/04/2026
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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03/04/2026 |
03/04/2026 |
Gustavia
Gustavia 03/05/2026
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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03/05/2026 |
03/05/2026 |
Basseterre, St. Kitts
Basseterre, St. Kitts 03/06/2026
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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03/06/2026 |
03/06/2026 |
St. Maarten (Philipsburg)
St. Maarten (Philipsburg) 03/07/2026
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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03/07/2026 |
03/07/2026 |