Windstar Cruises has raised Caribbean pricing for fall and winter while larger vessels in the region absorb the pricing pressure the rest of the industry reports, President Chris Prelog said on an Oct. 8 media call.

"We are not seeing any pricing pressure," Prelog said. "In fact, we're doing the opposite and have been able to raise prices in the Caribbean."

The line has also booked multiple Caribbean charters, executives said. Chief Commercial Officer Janet Bava tied the result to Windstar's ship size and port access. "Our smaller harbors are helping us probably sell our Caribbean season so much stronger," she said.

Why are bigger Caribbean ships under pressure?

The contrast is sharp against a wider Caribbean market where headline-grabbing new capacity has coincided with softening pricing. Windstar's smaller ships call at harbors the big ships cannot reach, Bava explained, so the line's product mix sits in a different competitive lane.

That pricing resilience carries direct consequences for retail sellers. Travel advisors booking Windstar's winter Caribbean can pitch a product that is moving up, not down, on the rate sheet, and the line has multi-charter commitments that lock in group and incentive business.

What new destinations is Windstar adding?

Prelog said Windstar is broadening its winter program beyond the Caribbean, adding the Canary Islands and a winter Mediterranean season as alternatives.

• Canary Islands: positioned as a snowbird option, with Bava citing new direct flights from Montreal and Toronto that give Canadian advisors a Caribbean substitute to sell.
• Winter Mediterranean: anchored by the new Star Explorer, debuting with a Dec. 28 New Year's sailing and including Carnival in Venice.

Prelog, who grew up in the Canaries, called the islands the "Hawaii of Europe" and pointed to their mix of Spanish and Portuguese culture, high mountains and black-sand beaches. Bava framed the wider winter portfolio as a trade tool. The Canaries and the winter Med now sit beside the Caribbean on advisor shelves for clients seeking warm-water or culturally rich escapes during the North American winter.

Will Windstar add short cruises from U.S. ports?

Short cruises out of U.S. homeports remain off the table, and COO Stijn Creuplandt explained why. "Miami, Bahamas, that doesn't really resonate," he said. "It's not really a Windstar product."

Bava added that Windstar's vessels need roughly two days to clear the Bahamas and reach destinations such as the Dominican Republic. The math, she said, works against a quick-turn U.S. itinerary, though she left the door cracked. "We have evaluated. We're just not keen on doing it, but never say never," she said.

What it means for sellers

The trade read on the call is straightforward. The line is leaning into differentiation rather than chasing volume: smaller ports, smaller ships, alternative winter geographies and pricing power in the Caribbean segment it dominates. For advisors, the practical consequence is a portfolio that includes a price-defiant winter product, a new Canaries option for Canadian snowbird clients, and a Mediterranean program fronted by the Star Explorer.

Windstar's strategy now hinges on whether its smaller-port advantage and alternative winter geographies can keep pricing firm as Caribbean capacity continues to grow into 2026.