Windstar Cruises has opened bookings for its Winter 2027-2028 season, a season that includes 21 new itineraries and more than 230 departure dates between September 2027 and April 2028 and multiple high-demand regions, including the South Pacific, Latin America and the Panama Canal, the Canary Islands and Morocco, Asia, the Caribbean and Canada & New England.
The Winter 2027-2028 program responds to the growing demand for smaller-ship cruises among luxury travelers, who prioritize less crowded destinations and deeper cultural experiences. With a mix of returning best-selling routes, extended Star Collector itineraries, and exclusive tours, the season offers advisors a wide range of options to plan ahead and create highly personalized recommendations.
“Travel agents are fundamental to Windstar’s success, and this season has been designed with their customers and their businesses in mind,” said Janet Bava, Chief Commercial Officer of Windstar Cruises. “Winter 2027-2028 includes unusual deployments, longer itineraries, and the kind of access only a smaller ship can offer. It’s a great opportunity to start conversations early and build meaningful, high-value voyages for their customers.”.
For a limited time, advisors can offer their clients additional benefits on selected Winter 2027-2028 departures, including:
– Complimentary All-Inclusive Package (Wi-Fi; unlimited beer, wine and selected cocktails; gratuities)
– Onboard credit
– Additional 5% savings for those who pay the full amount at the time of booking
Early bird offers are available on selected trips through April 30, 2026. Fares will increase as departures fill up.
The early launch of this season aligns with key trends among luxury and experiential travelers: increased long-term planning, interest in less crowded destinations, and demand for more immersive itineraries. The season also includes the highly anticipated Star Explorer motor yacht, whose winter Mediterranean itineraries were previously released.
Windstar yachts accommodate between 148 and 342 guests and offer an experience closer to sailing on a private yacht than a traditional cruise. They can dock closer to historic city centers, navigate narrow waterways, and access small harbors inaccessible to larger ships.
The fleet includes classic sailing yachts and modern motor yachts with suites, designed for destination-focused travel. The newest addition, Star Seeker, incorporates advanced environmental systems while maintaining the brand's signature comfort.
Each trip includes perks such as specialty dining in partnership with the James Beard Foundation, 24-hour room service, an exclusive outdoor barbecue, a champagne welcome, and access to wellness facilities. Select departures also feature Destination Discovery Events, exclusive one-night cultural experiences.
Main regions for Winter 2027-2028
– South Pacific – Star Breeze
Full 52-night trip from Papeete to Singapore, with shorter options such as a 14-night itinerary between Papeete and Fiji or a 24-day tour from Fiji to Singapore with an overnight stay in Bali.
– Latin America – Star Pride
Returns to itineraries through Costa Rica and the Panama Canal, with narrated daytime transit through the canal, wildlife viewing and land options to Machu Picchu and the Arenal volcano.
– Canary Islands – Wind Spirit
New itinerary from Malaga to Tenerife with more in-depth exploration of Morocco and two full days in Casablanca. Hidden Gems of the Canary Islands & Madeira returns with a special New Year's departure.
– Asia – Star Seeker
Extended programs with travel through Japan, Southeast Asia and Star Collector routes of 20 to 41 days, including access to downtown Ho Chi Minh City and Bangkok and extensions to Angkor Wat, Hanoi and Chiang Mai.
– Caribbean – Star Pride, Star Legend and Wind Surf
Island itineraries with access to small ports, water sports from private marina, Signature Beach Party and new routes through the ABC islands and the British Virgin Islands.
– Canada & New England – Star Pride
Includes Southeast Canada Exploration, special Celtic Colours Festival departure, Quebec & Newfoundland Adventure and Greenland: North Atlantic Odyssey from Reykjavik to Boston.
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