Windstar says it has raised Caribbean prices this winter while others face pressure to cut

Cruise linesBy Patrick KarshOct 15, 2026

The wider cruise market is seeing pressure on Caribbean prices this fall and winter. Windstar Cruises says it is not. The small-ship line told reporters it has raised its Caribbean prices and sees no pressure to discount them.

Windstar's leaders spoke on a media call on October 8, as reported by Cruise Industry News.

Why Windstar says it is different

President Chris Prelog said Windstar is seeing no pricing pressure in the region and has raised its fares there. The line has also signed several charters in the Caribbean, where a group books a whole ship.

Chief commercial officer Janet Bava gave the credit to ship size. Windstar runs small ships that carry a few hundred guests. "Our smaller harbors are helping us probably sell our Caribbean season so much stronger," she said.

The point is simple. Big ships tend to call at the same large ports and private islands. A small ship can tie up in harbors that a 5,000-guest ship cannot use. For a guest, that means a quieter port day. For the line, it means a product that is harder to compare on price alone.

More winter choices outside the Caribbean

Windstar is also building a winter program away from the Caribbean. It is adding more cruises in the Canary Islands and in the Mediterranean.

The newest ship leads the way. Star Explorer starts its first winter in the Mediterranean with a New Year's sailing on December 28. One of its winter trips is built around Carnival in Venice.

Bava said the winter Mediterranean gives travelers another option to the Caribbean. The line also pointed to more direct flights from Montreal and Toronto to the Canaries, which give Canadian travel agents another winter trip to sell.

No short cruises from US ports

Windstar has looked at short cruises from US ports, the kind of three- and four-night trips the big lines run from Florida. It has decided against them for now.

The ships need about two days to reach places like the Dominican Republic, the team said. Chief operating officer Stijn Creuplandt said that kind of trip does not fit a line built around time in port. "It's not really a Windstar product," he said. Bava added that the line is "just not keen on doing it, but never say never."

What this means for your booking

If you are shopping for a Windstar Caribbean cruise, do not wait for a big sale. The line is telling the market it does not need one. If a fare looks right for your dates, it may be worth booking rather than holding out.

If the Caribbean fares feel high, the winter Mediterranean and Canary Islands sailings are worth a look. They are a newer part of Windstar's winter lineup, and the weather is cooler than in the Caribbean. Compare what each fare includes, too. Small-ship fares can look high next to a mainstream line, but extras such as drinks, tips and tours can change the gap.

Finally, think about the type of port day you want. A crowded port with three megaships alongside is a very different day from a small harbor with one yacht-style ship. That difference is what Windstar is charging for.

My take

Windstar's message is that small ships are a different product, not a cheaper version of a big one, and the pricing backs that up. I would not expect deep Caribbean discounts from it this winter. If your dates are flexible, I would also look at Star Explorer's first Mediterranean winter.