Now Open for Booking: 21 New Itineraries Across Tahiti, Asia, the Caribbean, Latin America, the Canary Islands and Beyond

As travelers increasingly seek out experiences that go beyond crowded ports and one-size-fits-all cruising, Windstar Cruises is leaning into what it does best: offering intimate small-ship journeys with uncommon access and deeper cultural discovery. That approach comes into full focus with the opening of bookings for Windstar’s Winter 2027-2028 season, which features a global lineup of more than 230 sailing dates, 21 new itineraries, and six luxury yachts sailing between September 2027 and April 2028.

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The newly released winter deployment spans some of the world’s most sought-after destinations, including Tahiti, the Panama Canal, the Canary Islands, Morocco, Asia, the Caribbean, Canada and New England. With ships carrying between 148 and 342 guests, Windstar’s small size allows travelers to reach destinations, harbors, and city centers that remain inaccessible to larger cruise ships.

“With Winter 2027-2028, we’re delivering one of the most diverse and destination-rich seasons in Windstar’s history,” said Janet Bava, chief commercial officer at Windstar Cruises. “From a rare one-time-only South Pacific crossing to immersive Asia itineraries and yacht-style cruising in the Caribbean and Canary Islands, this season is designed for travelers who want deeper discovery, meaningful cultural experiences, and the freedom and access that only small ships can provide.”

Why Should You Book Winter 2027-2028 Cruises Now?
Travel demand for small ship cruising is continuing to grow as travelers prioritize uncrowded destinations and immersive itineraries. At the same time, long-range planning has become more popular for premium travel, allowing guests to secure preferred staterooms, longer itineraries, and limited-availability sailings well in advance.

Windstar’s Winter 2027-2028 season reflects these trends, with:

• One-season-only itineraries that will not be repeated
• Expanded longer voyages and Star Collector sailings
• Access to smaller ports and city centers unavailable to large cruise ships

To mark the launch, Windstar is offering an Early Booking Offer on select Winter 2027-2028 voyages. Guests who book by April 30, 2026 receive a complimentary All-Inclusive experience (Wi-Fi; select unlimited wine, beer, and cocktails; and gratuities), $100 onboard credit per guest, and the opportunity to save an additional 5% when paying in full at the time of booking. Fares will increase as voyages fill.

What Makes Windstar Ships So Unique?
Windstar Cruises delivers a style of travel that feels more like sailing on a private yacht than a traditional cruise ship. With just 148 to 342 guests, Windstar’s small ships can dock closer to historic city centers, navigate narrow waterways, and call on smaller ports where larger cruise ships simply can’t go. That access translates into longer stays in port, late evening departures, and more freedom to explore, whether independently or through Windstar’s curated shore experiences. In warm climates, the yachts’ marina lets guests access the sea directly from the ship to swim, relax on floating loungers, paddle board or go for a kayak.

Designed to feel more like private yachts than cruise ships, Windstar’s yachts blend classic sailing vessels with modern, all-suite motor yachts, each purpose-built for destination-focused cruising. 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:

• Complimentary specialty dining, with menus inspired by local cuisine and created in collaboration with the James Beard Foundation
• 24-hour complimentary room service
• A signature open-air deck barbecue
• A champagne welcome
• Complimentary access to the fitness center, whirlpools, sauna and yoga classes, reflecting Windstar’s holistic approach to wellness

Select sailings also feature Destination Discovery Events: exclusive, one-night cultural experiences ashore that combine local cuisine, music, and performance in historic or seldom-accessed settings.

Where Will Windstar’s Ships Sail in Winter 2027-2028?
Windstar’s Winter 2027-2028 season spans multiple regions and travel styles, from once-in-a-lifetime crossings and culturally immersive itineraries to relaxed island-hopping and expedition-style exploration. Here are some of the highlights.

South Pacific with Star Breeze
Winter 2027-2028 introduces a one-season-only South Pacific deployment as Star Breeze sails to and from drydock in Singapore, an itinerary that will not be repeated in future years. The season also features a 14-day voyage from Papeete to Lautoka, Fiji, with calls in Bora Bora, Moorea, the Cook Islands, and Tonga. The 24-day Fiji-to-Singapore itinerary sails through Papua New Guinea, the Solomon Islands, Vanuatu, and Indonesia with an overnight in Bali. Guests can combine select sailings into an extraordinary 53-day crossing between French Polynesia and Singapore. 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.

How is Windstar Making Winter 2027-2028 Voyages Unforgettable?
Beyond the itineraries, Windstar’s Winter 2027-2028 season is defined by experiences that bring destinations to life in unexpected ways. Guests can step directly from the ship’s marina into turquoise waters for a swim, share a beach barbecue under the stars, or explore ports late into the evening when day-trippers have gone home.

Windstar further enhances its small-ship access with expert-led experiences, from narrated Panama Canal transits and wildlife-focused sailings to culturally immersive shore programs and multi-day overland journeys to iconic spots such as Machu Picchu, Angkor Wat, and Hanoi. The result is travel that feels deeply personal, unhurried, and rich in story.

How to Book Winter 2027-2028 Cruises

• Winter 2027-2028 voyages are open for booking now, with Windstar’s Early Booking Offer available on select sailings through April 30, 2026. Guests who book early enjoy the best fares of the season, the widest choice of staterooms and suites, and added value including a complimentary All-Inclusive experience, onboard credit, and the opportunity to save an additional 5% when paying in full at the time of booking.
• To plan a small ship cruise with Windstar, guests can book online at windstarcruises.com, work with a travel advisor, contact Windstar Cruises by phone at 866-258-7245, or request a call from a Windstar vacation planner.

Windstar Cruises imagery here, credit to Windstar Cruises.

About Windstar Cruises:

For four decades, Windstar Cruises has been reimagining small-ship cruising with a distinctive blend of relaxed luxury and genuine connection to the world’s most captivating destinations. From its origins with motor sailing yachts tailored for upscale yet casual travel, Windstar has grown into a diverse fleet of four Star Class all-suite yachts—including its newest addition of Star Seeker in December 2025—and three Wind Class sailing yachts, offering voyages that are both intimate and inspiring. It’s highly anticipated yacht, Star Explorer, is set to debut in December 2026, expanding the fleet to eight yachts accommodating 150-350 guests. Windstar’s legendary Wind Class sailing yachts are also undergoing a meticulous two-phase redesign to be completed by 2027. Windstar yachts sail to more than 330 ports across Europe, the Caribbean, Costa Rica and the Panama Canal, Alaska, Canada and New England, Japan, the South Pacific, and Asia. Unlike most cruise lines, Windstar sails year-round in the Mediterranean and Tahiti, offering different destination experiences seasonally. Each Windstar voyage is designed to immerse guests in authentic cultural experiences, all while delivering the comfort, service, and style that define the Windstar difference.

Windstar Cruises is proud to be part of the Xanterra Travel Collection®, a distinguished group of global hospitality and travel companies with a legacy spanning over a hundred years. Xanterra operates iconic national parks, including Grand Canyon, Yellowstone, Glacier, and Death Valley. The Xanterra Travel Collection® is owned by The Anschutz Corporation, the ultimate owner of the Broadmoor, Sea Island, and entertainment giant AEG, Anschutz Entertainment Group.

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