San Juan
San Juan 03/27/2026
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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03/27/2026 |
03/27/2026 |
Cruz Bay, St. John
Cruz Bay, St. John 03/28/2026
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
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03/28/2026 |
03/28/2026 |
St. John's, Antigua
St. John's, Antigua 03/29/2026
St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors. The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you. Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.
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03/29/2026 |
03/29/2026 |
Iles des Saintes
Iles des Saintes 03/30/2026
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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03/30/2026 |
03/30/2026 |
Pigeon Island, St. Lucia
Pigeon Island, St. Lucia 03/31/2026
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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03/31/2026 |
03/31/2026 |
St. George's, Grenada
St. George's, Grenada 04/01/2026
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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04/01/2026 |
04/01/2026 |
At Sea
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04/02/2026 |
04/02/2026 |
Gustavia
Gustavia 04/03/2026
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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04/03/2026 |
04/03/2026 |
Jost Van Dyke
Jost Van Dyke 04/04/2026
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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04/04/2026 |
04/04/2026 |
Virgin Gorda
Virgin Gorda 04/05/2026
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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04/05/2026 |
04/05/2026 |
San Juan
San Juan 04/06/2026
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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04/06/2026 |
04/06/2026 |