Windstar Cruises Says Caribbean Fares Are Rising and Sets Star Explorer’s First Sailing for December 28

October 9, 2026 — Windstar Cruises says it has raised Caribbean fares while larger lines face pricing pressure there, and its new 224-guest Star Explorer will take its first guests on December 28.

Executives spoke on a media call on October 8, Cruise Industry News reports. President Chris Prelog said the line is “doing the opposite” of discounting in the Caribbean and has secured several charters there.

Caribbean pricing and winter alternatives

Why fares are holding: Chief Commercial Officer Janet Bava said Windstar’s small ships use smaller harbors that large ships cannot reach.
New winter options: the line now sells the Canary Islands and a winter Mediterranean season as alternatives to the Caribbean.
Flights to the Canaries: Bava said there are more direct flights from Montreal and Toronto.
No short U.S. cruises: Chief Operating Officer Stijn Creuplandt said Miami–Bahamas trips are not a Windstar product. Bava added that the idea was evaluated and set aside.

Star Explorer timeline

Milestone	Date
Delivery	December 2026; exact day TBA
First guest sailing (New Year’s voyage)	December 28, 2026
Mediterranean deployment	Winter and spring 2027, including Carnival in Venice
Naming ceremony and inaugural voyage, London	June 1, 2027

Prelog said he expects delivery on time and sees no outstanding challenges. Embarkation port for the December 28 sailing: TBA in the reports.

Lessons from sister ship Star Seeker

Dining: the galley sits a deck below the restaurant, which slowed service. Waiters now send orders by tablet. Star Explorer will launch with the system and the rest of the fleet will follow.
Fresh water: Star Explorer gets more holding capacity for its itineraries.
Ratings: Creuplandt called Star Seeker “one of the highest rated ships in the fleet.”

What it means for airline travelers

Do not wait for Caribbean discounts. Windstar says fares are going up and charters are taking inventory.
December 28 is peak holiday flying. Standby loads to Europe are at their worst that week. Arrive at least two days early, or buy a ticket.
Canaries from Canada: the Montreal and Toronto nonstops help staff with access to Canadian carriers. Others will connect through mainland Europe.
Windstar’s U.S.-based travelers still need a long flight. The line has no plan for short cruises from U.S. ports.
Interline rates: none were mentioned on the call. Windstar has offered airline-crew fares before, so ask your interline agent what is current.