Windstar Cruises has opened bookings for its Winter 2027-2028 season, giving travel advisors access to a global deployment that includes 21 new itineraries and more than 230 sailing dates between September 2027 and April 2028. The newly released season spans 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 deployment builds on growing demand for small-ship cruising among luxury travelers who are prioritizing uncrowded destinations and deeper cultural experiences. With a mix of returning top-selling routes, extended Star Collector sailings, and exclusive itineraries, the season provides advisors with a broad range of options to support advance planning and highly customized client recommendations.
“Advisors are central to Windstar’s success, and this season was built with their clients and their businesses in mind,” Janet Bava, chief commercial officer at Windstar Cruises, said in a statement. “Winter 2027-2028 offers rare deployments, longer itineraries, and the kind of small-ship access that larger cruise lines simply can’t offer. It gives advisors a powerful opportunity to start conversations early and build meaningful, high-value journeys for their clients.”
Early Booking Offer Supports Advisor Sales Conversations
For a limited time, advisors can offer clients added value on select Winter 2027-2028 sailings, including:
- A complimentary All-Inclusive package (Wi-Fi; unlimited select beer, wine, and cocktails; gratuities)
- $100 onboard credit per guest
- The opportunity to save an additional 5 percent when clients pay in full at the time of booking
Early booking offers are available on select voyages through April 30, 2026. Fares will increase as voyages fill.
Why Winter 2027-2028 Is a Strong Selling Window for Advisors
Windstar’s release of its Winter 2027-2028 season aligns with key booking trends among luxury and experiential travelers, including longer planning horizons, interest in uncrowded destinations, and demand for more immersive itineraries. The season also welcomes Windstar’s highly anticipated motor yacht, Star Explorer, with winter itineraries in the Mediterranean. Opening this 2027/2028 season now allows advisors to:
- Secure preferred suites before inventory tightens
- Sell longer voyages and Star Collector itineraries with higher per-booking value
- Leverage one-season-only deployments that create urgency and scarcity
- Position Windstar as a differentiated alternative to mass-market and large-ship cruising
Windstar’s yachts accommodate just 148 to 342 guests and deliver a style of cruising that feels closer to sailing on a private yacht than a traditional cruise ship. Windstar’s yachts can dock closer to historic city centers, navigate narrow waterways, and call on smaller ports that are inaccessible to larger ships.
The fleet includes classic sailing vessels and modern, all-suite motor yachts, each purpose-built for destination-focused travel. The newest yacht, Star Seeker, has been built with advanced environmental systems while maintaining the brand’s signature comforts, from spacious suites and open decks to highly personalized service.
Every Windstar voyage includes features that reinforce value while simplifying the sales conversation, including complimentary specialty dining created in collaboration with the James Beard Foundation, 24-hour room service, a signature open-air deck barbecue, a champagne welcome, and complimentary access to wellness amenities. Select sailings also feature Destination Discovery Events, exclusive, one-night cultural experiences. These features add a clear point of differentiation that advisors can use to elevate the overall journey.
Key Regions Advisors Can Sell for Winter 2027-2028
Windstar’s Winter 2027-2028 season spans a broad range of destinations and selling opportunities, including:
South Pacific with Star Breeze
The full 52-night voyage sails from Papeete to Singapore, visiting destinations from the Marquesas Islands to Indonesia. Windstar is also offering shorter segments of this voyage, including a 14-night sailing from Papeete to Lautoka, Fiji, with stops in Bora Bora, Moorea, the Cook Islands, and Tonga. Another option is a 24-day itinerary from Fiji to Singapore, traveling through Papua New Guinea, the Solomon Islands, Vanuatu, and Indonesia, with an overnight in Bali. In 2027, Wind Star will be joining Star Breeze as the second yacht for year-round sailings in Tahiti. Wind Star Tahiti itineraries for 2027 are available for booking now.
Latin America with Star Pride
Windstar’s signature Costa Rica and Panama Canal voyages return with multiple itinerary options designed around nature, wildlife, and engineering marvels. Highlights include a bucket list daytime Panama Canal transit narrated by an onboard expert, wildlife encounters, explorations in rainforests and national parks, and optional cruise tours to Machu Picchu and Arenal Volcano, two of Windstar’s most popular and fast-selling extensions.
Canary Islands with Wind Spirit
A new itinerary debuts for Winter 2027-2028, sailing from Málaga in southern Spain to Tenerife in the Canary Islands with deeper exploration in Morocco, including two full days in Casablanca. The popular Hidden Gems of the Canary Islands & Madeira itinerary returns with a New Year’s Celebration voyage featuring an overnight in Madeira timed to the island’s world-famous fireworks.
Asia with Star Seeker
The brand-new Star Seeker anchors Windstar’s expanded Asia program with Grand Japan sailings, Southeast Asia itineraries, and longer Star Collector voyages ranging from 20 to 41 days. Small-ship advantages include docking in the heart of Ho Chi Minh City and Bangkok, access to lesser-visited islands, and overland tours to iconic destinations like Angkor Wat, Hanoi, and Chiang Mai.
Caribbean with Star Pride, Star Legend and Wind Surf
Windstar’s Winter Caribbean season offers departures aboard both all-suite yachts and classic sailing ships, combining relaxed island hopping with access to smaller harbors that larger ships can’t reach. Highlights include marina access for water sports, Windstar’s Signature Beach Party, and new routings through the ABC Islands (Aruba, Bonaire, and Curaçao) and the British Virgin Islands.
Canada & New England with Star Pride
Late-season voyages bring a fresh perspective on North America, with the updated Southeast Canada Exploration (featuring an overnight in Halifax), a special Celtic Colours Festival sailing, the return of the Quebec & Newfoundland Adventure, and the Greenland: North Atlantic Odyssey voyage from Reykjavík to Boston.
Booking Information for Travel Advisors
Winter 2027-2028 voyages are open for booking now, with Early Booking Offers available on select sailings through April 30, 2026.
- Best suite selection: Early booking supports access to the most desirable suites, particularly on longer and limited-deployment itineraries
- Inventory advantage: One-season-only deployments and extended itineraries benefit from early confirmation
- To book: Advisors can book online here, call 866-258-7245, or request a call from a Windstar vacation planner.
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