Windstar Cruises Opens Bookings for Winter 2027-28 Sailings

Bookings are now open for Windstar Cruises winter 2027/28 voyages.

From September 2027 to April 2028, the brand will offer 21 new itineraries and more than 230 sailing dates to in-demand destinations in the South Pacific, Latin America, the Canary Islands, Morocco, Asia, the Caribbean and Canada and New England.

The season also features Windstar’s new motor yacht, Star Explorer, which is slated to debut in December 2026.

From now through April 30, travel advisors can offer their clients added value on select sailings, including a free All-Inclusive package (which includes Wi-Fi; unlimited select beer, wine, and cocktails; and gratuities), a $100 onboard credit per guest and an additional 5 percent savings on paid-in-full bookings. 

“Advisors are central to Windstar’s success, and this season was built with their clients and their businesses in mind,” says Janet Bava, chief commercial officer at Windstar Cruises.

“Winter 2027-2028 offers rare deployments, longer itineraries and the kind of small-ship access that larger cruise lines simply can’t offer,” Bava continued. “It gives advisors a powerful opportunity to start conversations early and build meaningful, high-value journeys for their clients.” 

This article originally appeared in TravelPulse.

Contact My Journey Begins Travel to plan and book with Windstar Cruises up to and including Winter 2027/28.

About Windstar Cruises

Windstar Cruises is a fleet of small luxury cruise ships that are known for their intimate yacht-style experience combined with voyages to some of the world’s best small ports and harbors. The fleet consists of three recently renovated sailing yachts that carry no more than 310 passengers and cruise to 50 nations. The ships call at 150 ports throughout Europe, the South Pacific, the Caribbean and Central America.

In addition to its sailing yachts, Windstar also acquired three suite yachts and, in May of 2014, it launched Star Pride. This year, Windstar followed with the launches of Star Breeze and Star Legend in May. Each of the all suite yachts hold 212 guests and their addition to the fleet doubles Windstar’s size, making the company one of the market leaders when it comes to small ship cruising with 300 or fewer passengers.

This additional capacity has opened up new itineraries for the cruise line, including voyages to Southeast Asia, Arabia, Iceland and beyond.