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.