Windstar Cruises has released its Winter 2027–2028 season for advance booking, unveiling a comprehensive program.
Windstar's small-ship voyages include 21 new global itineraries and 230+ departure dates between September 2027 and April 2028. They span multiple regions of strong demand for boutique cruising, incorporating extended passages in the South Pacific, Latin America and the Panama Canal, the Canary Islands and Morocco, Asia, the Caribbean, and the Canada & New England coast.
The season’s deployment builds on Windstar’s positioning within the luxury small-ship segment, where vessels with capacities ranging from approximately 148 to 342 guests offer access to smaller harbors and culturally rich destinations that larger ships cannot reach.
Among the highlights are long South Pacific crossings aboard Star Breeze, including a full 52-night voyage from Papeete to Singapore with shorter segments also available; return sailings through the Panama Canal and coastal Latin America aboard Star Pride; and a new Canary Islands route from Málaga to Tenerife featuring extended time in Morocco.
In Asia, Star Seeker anchors an expanded program of Grand Japan and Southeast Asian voyages, combining sea days with calls at ports such as Ho Chi Minh City and Bangkok and opportunities for overland excursions to cultural landmarks.
The Caribbean schedule deploys both all-suite yachts and classic sailing vessels, emphasising island hopping and access to marinas and smaller anchorages.
Late-season North American sailings include updated Canada & New England itineraries with overnight stays in Halifax and explorations such as a Greenland passage from Reykjavík to Boston.
Bookings opened on February 18th, with early booking offers available on select sailings through April 30th, 2026, providing incentives such as complimentary all-inclusive packages covering connectivity, selected beverages and gratuities, onboard credits and savings for full-payment reservations.
The timing of the release reflects broader planning trends among luxury and experiential travelers, with agents encouraged to secure preferred cabins and promote longer, higher-value voyages well ahead of departure dates.
Windstar’s newest yacht, Star Explorer/now World Explorer (2019-built), is scheduled to enter service in December 2026 and is anticipated to complement the winter season with its own suite of itineraries, further enhancing the line’s small-ship options.