Windstar Opens Winter 2027-2028 Season With 21 New Itineraries

Windstar Cruises has opened bookings for its Winter 2027–2028 season, unveiling 21 new itineraries and more than 230 sailing dates between September 2027 and April 2028. In practical terms, this means there will be a small flotilla of very elegant ships gliding about the globe at precisely the moment most of us are scraping ice off windshields. The season stretches ambitiously across the South Pacific, Latin America and the Panama Canal, the Canary Islands and Morocco, Asia, the Caribbean, and Canada and New England — which is to say, nearly everywhere you might reasonably wish to be between autumn and spring.

The deployment blends Windstar’s returning favorites with extended “Star Collector” voyages and new, exclusive itineraries — all thoughtfully arranged for travelers who prefer their luxury intimate and their ships sensibly proportioned. As Janet Bava, Windstar’s chief commercial officer, puts it, the season is designed with travel advisors — and their clients — firmly in mind. Small ships, she notes, can slip into ports that larger vessels can only gaze at wistfully from offshore, which is rather like having the keys to a side entrance everyone else forgot existed.

For a limited time, select winter sailings come with a complimentary all-inclusive package covering Wi-Fi, unlimited select beer, wine and cocktails, gratuities, $100 onboard credit per guest, and an additional five percent savings for those who pay in full at booking. Early booking offers run through April 30, 2026, after which fares will rise in that polite but unmistakable way travel prices tend to do.

The season reflects a growing preference among luxury travelers for longer planning horizons, fewer crowds, and deeper immersion — a desire not merely to see a place, but to experience it without standing in line behind several thousand of one’s closest strangers.

Windstar’s fleet consists of ships carrying between 148 and 342 guests, a number small enough that you might eventually recognize your fellow passengers but large enough that no one expects you to. The line operates both classic sailing vessels and all-suite motor yachts designed to dock close to historic centers, navigate narrow waterways, and access ports that larger ships avoid entirely. The newest yacht, Star Seeker, incorporates advanced environmental systems while maintaining Windstar’s signature suites, open decks, and notably attentive service.

Onboard life leans toward the civilized. Dining is created in collaboration with the James Beard Foundation, room service operates around the clock, there is an open-air deck barbecue, a champagne welcome, and wellness amenities for those who wish to return home slightly improved. Select sailings include Destination Discovery Events — one-night cultural experiences that aim to make you feel less like a visitor and more like a temporarily adopted local.

In the South Pacific, Star Breeze undertakes a particularly ambitious 52-night voyage from Papeete to Singapore, linking the Marquesas Islands with Indonesia in one sweeping arc. Shorter segments include a 14-night sailing from Papeete to Lautoka, calling at Bora Bora, Moorea, the Cook Islands, and Tonga, and a 24-day journey from Fiji to Singapore via Papua New Guinea, the Solomon Islands, Vanuatu, and Indonesia — with an overnight in Bali for good measure. In 2027, Wind Star joins Star Breeze for year-round Tahiti sailings, ensuring there is always someone sensibly heading toward turquoise water.

In Latin America, Star Pride returns to Costa Rica and Panama Canal routes, featuring a daytime canal transit narrated by an onboard expert — which is exactly the sort of detail that makes crossing one of the world’s great engineering marvels feel appropriately momentous. Wildlife encounters, rainforest explorations, and optional extensions to Machu Picchu and Arenal Volcano round out the experience.

In the Canary Islands, Wind Spirit introduces a new route from Málaga to Tenerife, with extended time in Morocco — including two full days in Casablanca — while the Hidden Gems of the Canary Islands and Madeira itinerary returns with a New Year’s sailing timed to coincide with Madeira’s famously exuberant fireworks.

Asia’s program is anchored by Star Seeker, offering Grand Japan sailings, Southeast Asia itineraries, and Star Collector voyages lasting up to 41 days. Ports include Ho Chi Minh City and Bangkok, along with smaller islands and optional overland visits to Angkor Wat, Hanoi, and Chiang Mai — destinations that reward lingering.

In the Caribbean, Star Pride, Star Legend, and Wind Surf operate itineraries that feature marina access for water sports, Windstar’s Signature Beach Party, and routes through the ABC Islands — Aruba, Bonaire, and Curaçao — as well as the British Virgin Islands, all approached with a refreshingly modest passenger count.

And for those who prefer their scenery bracing, Star Pride sails updated Canada and New England itineraries, including an overnight in Halifax, a Celtic Colors Festival voyage, the return of Quebec and Newfoundland Adventure, and the Greenland: North Atlantic Odyssey from Reykjavík to Boston — a journey that replaces palm trees with icebergs and feels all the more invigorating for it.

In short, Windstar’s Winter 2027–2028 season offers a pleasing proposition: the world, thoughtfully arranged, reached by ships small enough to feel personal and large enough to feel indulgent — which may be the most civilized way to travel after all.