Windstar Cruises: The Long Way Home

Anyone who has ever been to the Caribbean has most likely contemplated extending their stay. While Windstar doesn’t offer residency, it gets pretty close with its 54-night Grand Caribbean Adventure cruise. Setting sail in January of 2026, the itinerary covers 28 sun-soaked islands, 39 ports, and 100-plus shore excursions that are fully vetted, authentically local, and truly unforgettable. With so many shore excursions available, “something for everyone” isn’t an understatement.

Cruises

TitleCruise LineShipNightsSailing DatePrice FromOffer ID
55-night Star Collector: A Grand Caribbean AdventureWindstar CruisesWind Surf55
01/04/2026
$16,9461512967

Cruise fares shown are the lowest available nationwide non-past-passenger fare. Other fares, which may be lower and/or include restrictions, may be available. Please view the full offer for complete details.