While some cruise lines are quietly discounting their Caribbean sailings this winter, Windstar Cruises is going the other way. President Chris Prelog said on an October 8 media call that the line has actually raised prices in the region and locked in multiple charters, bucking the soft pricing reportedly hitting the wider Caribbean market.
Why is Windstar immune? Chief Commercial Officer Janet Bava points to ship size. The line's small vessels don't call at the same ports as the mega-ships that are feeling the squeeze, since those big vessels are restricted to a limited set of islands. Smaller harbours, she argued, are a big reason the Caribbean season is selling so well for Windstar.
The line isn't resting on the Caribbean alone, though. Prelog said Windstar is expanding its winter programme for repeat guests who want somewhere new. The options: the Canary Islands and a winter Mediterranean season. He knows the Canaries well, having spent much of his childhood there, and makes the case that they've earned the nickname "the Hawaii of Europe" — Spanish and Portuguese culture and food, plus everything from high mountains to black-sand beaches. Bava also flagged growing direct flights from Montreal and Toronto, which gives Canadian travellers an alternative to the usual snowbird routes.
Meanwhile, the new Star Explorer will spend its first winter in the Mediterranean, kicking off with a New Year's sailing on December 28, with itineraries that include Carnival in Venice. Bava framed the whole winter Med season as a genuine alternative to the Caribbean rather than a fallback.
One thing Windstar won't be doing is short cruises from U.S. ports. COO Stijn Creuplandt was blunt about it: a quick Miami-to-Bahamas run "doesn't really resonate" with the line's destination-focused style, especially since the ships need roughly two days just to clear the Bahamas before reaching places like the Dominican Republic. He and Bava said they've evaluated the idea and aren't keen — though they left the door slightly ajar with a "never say never."
For travellers, this is a useful signal. If you prefer small ships, quieter ports and itineraries built around the destination rather than the onboard scene, Windstar's winter options are expanding — and its Caribbean pricing suggests demand for that style is holding firm. It's also a nudge to consider the Canary Islands or a winter Med sailing instead of the usual Caribbean loop, particularly if you're flying from eastern Canada.
