Windstar 11-Night Leeward Islands Cruise for From $15,076 for 2

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Sail roundtrip from San Juan aboard Windstar's Star Pride on an 11-night Caribbean cruise through the Leeward Islands. The itinerary visits St. John, St. Barts, St. Kitts, Antigua, Guadeloupe, St. Lucia, Grenada, Jost Van Dyke, and Virgin Gorda. A complimentary all-in package and reduced deposit are included. Book this travel deal by September 30, 2026.Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises Features 11 nights aboard S