Windstar Cruises has opened bookings for its Winter 2027–2028 season, unveiling 21 new itineraries and over 230 sailing dates across Tahiti, Asia, the Caribbean, and more. This season will run from September 2027 to April 2028 and emphasizes small-ship journeys that provide deeper cultural immersion and access to ports larger ships cannot reach.
Why book Winter 2027–2028 now?
The demand for small-ship cruising is on the rise as travelers seek less crowded destinations, extended stays, and immersive itineraries. The upcoming season offers:
- One-season-only itineraries that won’t be repeated.
- Expanded long voyages and Star Collector sailings.
- Access to smaller ports and city centers.
Early Booking Offer: Book by April 30, 2026, to get a complimentary All-Inclusive experience, US$100 onboard credit per guest, and potential extra savings of 5% when paying in full at booking.
Unique aspects of Windstar’s ships
Windstar’s yachts accommodate just 148 to 342 guests, creating a more intimate atmosphere akin to a private yacht. Key advantages include:
- Docking close to historic centers and navigating narrow waterways.
- Access to smaller harbors and islands.
- Longer stays in port.
Windstar’s fleet combines classic sailing vessels with modern motor yachts, featuring amenities like specialty dining, fitness access, and more.
Itinerary Highlights
South Pacific with Star Breeze
- A 14-day voyage from Papeete to Lautoka.
- A 24-day journey from Fiji to Singapore with an overnight in Bali.
Latin America with Star Pride
- Costa Rica and Panama Canal cruises with narrated canal transits.
Caribbean & Mediterranean with Wind Spirit
- New routes through Tenerife and extended stays in Morocco.
Asia with Star Seeker
- Enhanced itineraries featuring longer voyages and overland tours.
Booking Information
Winter 2027–2028 voyages are available now, with early booking offers until April 30, 2026. Travelers can book online or through a travel advisor.
