The winter of 2027-2028 marks a new chapter for Windstar Cruises, as the cruise line unveils a global deployment featuring 21 new itineraries across the world’s most sought-after regions. Designed for the luxury traveler who prioritizes uncrowded destinations and deep cultural immersion, this season spans the South Pacific, Latin America, the Canary Islands, Asia, and the Caribbean.
The Small-Ship Advantage: Access Without Compromise
In an era of increasingly large cruise ships, Windstar remains dedicated to the intimacy of yacht-style travel. With vessels accommodating just 148 to 342 guests, the experience feels closer to sailing on a private yacht than a traditional ship. These smaller dimensions allow the fleet to dock in the heart of historic city centers, navigate narrow waterways, and call on tiny ports that remain untouched by the masses.
The fleet – comprising both classic sailing vessels and modern, all-suite motor yachts – continues to lead in destination-focused travel. This season also welcomes the highly anticipated Star Explorer. Thogether with the recently launched Star Seeker, these state-of-the-art yachts feature advanced environmental systems while maintaining Windstar’s signature comforts, from expansive open decks to highly personalized service.
Culinary Excellence and Wellness
Every Windstar voyage includes gourmet experiences created in collaboration with the James Beard Foundation. From 24-hour room service to the signature open-air deck barbecue and a champagne welcome, every detail is designed for indulgence. Select sailings also feature Destination Discovery Events – exclusive, one-night cultural experiences that bring the essence of the locale to life.
Exceptional Value and Early Rewards
Travelers planning their 2027-2028 winter escape can benefit from exclusive added value on select sailings through April 30, 2026. These early-planning perks include:
- A complimentary All-Inclusive package: Including Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities.
- $100 onboard credit per guest to spend as you wish.
- An additional 5% saving for those who choose to pay in full at the time of reservation.
Destinational Highlights
The South Pacific: A Polynesian Dream
The Star Breeze embarks on a grand 52-night voyage from Papeete to Singapore, visiting the Marquesas Islands and Indonesia. For those seeking shorter adventures, 14-night segments explore Fiji, Tonga, and the Cook Islands. Notably, the classic Wind Star will join the Star Breeze in 2027, offering two yachts for year-round exploration of the Tahitian islands.
Asia: Deep Immersion with Star Seeker
The brand-new Star Seeker anchors an expanded Asia program, featuring Grand Japan sailings and Southeast Asia itineraries. The small-ship advantage is on full display here, as guests can dock in the very heart of Ho Chi Minh City and Bangkok. Overland tours to iconic sites like Angkor Wat and Hanoi further enrich the journey.
Latin America & The Panama Canal
Windstar’s signature Costa Rica and Panama Canal voyages return, highlighting nature and engineering marvels. Guests can enjoy a daytime canal transit narrated by experts, wildlife encounters in rainforests, and optional extensions to Machu Picchu or the Arenal Volcano.
The Canary Islands & Morocco
A new itinerary debuts, sailing from Málaga to Tenerife with deep exploration of Morocco, including two full days in Casablanca. The popular Hidden Gems of the Canary Islands & Madeira route also returns, featuring a spectacular New Year’s Celebration voyage in Madeira.
Caribbean & North America
Whether aboard an all-suite yacht or a classic sailing ship, Windstar’s Caribbean season offers relaxed island hopping through the ABC Islands and the British Virgin Islands. Further north, late-season voyages in Canada and New England bring a fresh perspective, including the Celtic Colours Festival and a North Atlantic Odyssey from Reykjavík to Boston.
Pictures Windstar Cruises.
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