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Star Collector: Caribbean Collection: ABC, BVI & the Windwards
Mar 6, 2028 — Mar 27, 2028
Starting from
ORANJESTAD, ARUBA → SAN JUAN
21 Nights on Star Pride
Travel through three distinct Caribbean regions on a route that offers broad geographic range and access to smaller ports. In the Windwards, sample spices in St. George’s and explore Bequia’s maritime traditions before sailing toward the ABC Islands for protected diving sites and colorful coastal towns. Continue north to Gustavia’s boutiques, Jost Van Dyke’s laid-back coves, and Virgin Gorda’s iconic Baths, where trails weave through giant granite boulders. San Juan’s Old World architecture and dining complete the experience. Throughout the itinerary, contrasting islands—arid ABC reefs, lush Grenadine bays, and BVI anchorages used by private yachts—create a journey rich in local culture, shoreline activities, and opportunities to enjoy the advantages of small-ship travel.
Popular Highlights
Visit 15 distinct ports across the ABC Islands, the Windwards, and the British Virgin Islands.
Wander through the Baths’ massive granite boulders on Virgin Gorda before relaxing on powder-white sands.
Swim from Jost Van Dyke’s Great Harbour to iconic beach bars serving Caribbean classics like the Painkiller.
Sail past Gustavia’s glowing harbor lights during a romantic sunset cruise with sparkling wine in hand.
Explore St. George’s horseshoe harbor with markets full of nutmeg, cinnamon, and local cocoa.
Snorkel off Bequia’s shoreline, then watch local builders create the miniature wooden sloops that define the island’s heritage.
Enjoy Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Enjoy complimentary laundry during your cruise.
Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just ... take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.
Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It's the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves-filled with eerie limestone formations and ancient petroglyphs.
The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you'll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface
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.
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.
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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