Windstar Cruises Announces Winter 2027–2028 Schedule with Enhanced Itineraries

Windstar Cruises has announced its Winter 2027–2028 schedule, which features an extensive range of voyages now available for advance booking. This season includes 21 new global itineraries and over 230 departure dates from September 2027 to April 2028. The newly planned routes cover popular boutique cruising regions such as the South Pacific, Latin America, Panama Canal, Caribbean, Canary Islands, Morocco, Asia, and the coasts of Canada and New England.

Windstar’s small-ship voyages capitalize on the luxury sector, allowing access to smaller harbors and unique cultural hotspots that larger vessels cannot reach, catering to up to 342 guests on its ships.

Notable itineraries include long oceanic passages through the South Pacific aboard the Star Breeze, featuring a 52-night journey from Papeete to Singapore with shorter segments also on offer. Additionally, Star Pride will operate routes through the Panama Canal alongside coastal Latin American trips. A new itinerary is also launched from Málaga to Tenerife, allowing for an extended stay in Morocco.

In Asia, Star Seeker will expand its Grand Japan and Southeast Asian voyages, combining days at sea with stops at significant ports like Ho Chi Minh City and Bangkok, offering overland excursions to key cultural sites.

In the Caribbean, both luxury yachts and classic sailing vessels will focus on island hopping, providing access to smaller anchorages. Late-season itineraries in North America include enriched Canada and New England routes with overnight stops in Halifax and a unique sailing passage from Reykjavík to Boston via Greenland.

Bookings were opened on February 18, 2026, with early booking promotions available until April 30, 2026, which encompass all-inclusive packages that cover connectivity, selected beverages, gratuities, onboard credits, and discounts for full payments.

Windstar is also preparing for the introduction of its latest yacht, the Star Explorer (formerly World Explorer), which will debut in December 2026, offering additional itineraries to enhance the line’s small-ship capabilities further.

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