Windstar Cruises Opens Winter 2027–2028 Season: 21 New Small-Ship Itineraries from Tahiti to Asia and the Canary Islands

Windstar Cruises has opened bookings for its Winter 2027–2028 season, unveiling 21 new itineraries and more than 230 sailing dates across Tahiti, Asia, the Caribbean, Latin America, the Canary Islands, Morocco, Canada and New England. The six‑yacht program, running from September 2027 to April 2028, leans into Windstar’s hallmark: small‑ship journeys with deeper cultural immersion and access to ports larger ships can’t reach.

Why book Winter 2027–2028 now?

Demand for small‑ship cruising continues to grow as travellers seek uncrowded destinations, longer stays and more immersive itineraries, while also planning premium trips further in advance to secure the best cabins and rare routes. Windstar’s new season taps into that trend with:

• One‑season‑only itineraries that won’t be repeated.
• Expanded longer voyages and Star Collector sailings.
• Access to smaller ports and city centres unavailable to large ships.

To launch the program, Windstar is offering an Early Booking Offer on select Winter 2027–2028 sailings: book by April 30, 2026 and receive a complimentary All‑Inclusive experience (Wi‑Fi, select unlimited wine, beer and cocktails, and gratuities), US$100 onboard credit per guest, and the chance to save an extra 5% when paying in full at booking. Fares will rise as sailings fill.

What makes Windstar’s small ships different?

Windstar’s yachts carry just 148 to 342 guests, creating a feel much closer to a private yacht than a traditional cruise ship. This compact size delivers several advantages:

• The ability to dock closer to historic city centres and navigate narrow waterways.
• Calls at smaller harbours and islands that mega‑ships can’t access.
• Longer days in port and late‑evening departures, giving guests time to explore after day‑trippers have left.

In warm regions, many ships feature a watersports marina that opens directly from the stern, letting guests swim, paddleboard, kayak or relax on floating loungers straight from the yacht.

Fleet highlights include classic sailing ships and all‑suite motor yachts, with new build Star Seeker bringing advanced environmental systems and the brand’s signature blend of spacious suites, open decks and personalised service.

Every Windstar voyage includes:

• Complimentary specialty dining, with menus crafted in partnership with the James Beard Foundation.
• 24‑hour room service.
• A signature open‑air deck barbecue and champagne welcome.
• Complimentary access to the fitness centre, whirlpools, sauna and yoga classes.

Select itineraries also feature Destination Discovery Events—one‑night, ashore experiences that combine local cuisine, music and performance in special venues not normally open to cruise guests.

Winter 2027–2028 regional highlights

South Pacific with Star Breeze

Winter 2027–2028 includes a one‑season‑only South Pacific deployment as Star Breeze repositions to and from drydock in Singapore—an opportunity Windstar does not plan to repeat. Standout sailings include:

• A 14‑day Papeete–Lautoka voyage visiting Bora Bora, Moorea, the Cook Islands and Tonga.
• A 24‑day Fiji–Singapore journey via Papua New Guinea, the Solomon Islands, Vanuatu and Indonesia, with an overnight in Bali.
• The option to combine select segments into a 53‑day crossing between French Polynesia and Singapore.

Year‑round Tahiti also expands as Wind Star joins Star Breeze as the second yacht based in French Polynesia in 2027.

Latin America with Star Pride

Windstar’s signature Costa Rica and Panama Canal cruises return on Star Pride, with itineraries centred on nature, rainforests and the engineering marvel of the canal. Guests can:

• Experience a daytime, narrated Panama Canal transit with expert commentary.
• Explore national parks and wildlife‑rich regions in Costa Rica and beyond.
• Add popular cruise tours to Machu Picchu and Arenal Volcano, both of which sell quickly.

Canary Islands & Morocco with Wind Spirit

A new itinerary sees Wind Spirit sail from Málaga in southern Spain to Tenerife in the Canary Islands, with extended exploration in Morocco, including two full days in Casablanca. The season also brings back the Hidden Gems of the Canary Islands & Madeira route, including a New Year’s Celebration with an overnight in Madeira timed for the island’s world‑famous fireworks.

Asia with Star Seeker

New yacht Star Seeker anchors an expanded Asia program, featuring:

• Grand Japan routes.
• Southeast Asia sailings and longer Star Collector voyages of 20–41 days.
• Small‑ship docking in the heart of Ho Chi Minh City and Bangkok, plus calls at lesser‑visited islands.
• Overland tours to Angkor Wat, Hanoi and Chiang Mai.

Caribbean with Star Pride, Star Legend and Wind Surf

Winter in the Caribbean features both all‑suite yachts and classic sailing ships, mixing relaxed island‑hopping with access to smaller harbours and tucked‑away bays. Guests can enjoy:

• Direct marina access for water sports.
• Windstar’s Signature Beach Party.
• New routes through the ABC Islands (Aruba, Bonaire, Curaçao) and the British Virgin Islands.

Canada & New England with Star Pride

Late‑season sailings in Canada & New England offer a different take on North America’s east coast. Highlights include:

• An updated Southeast Canada Exploration with an overnight in Halifax.
• A Celtic Colours Festival voyage timed to the celebrated Cape Breton event.
• The return of Quebec & Newfoundland Adventure.
• Greenland: North Atlantic Odyssey from Reykjavík to Boston.

Experiences that make these voyages memorable

Across regions, Windstar’s Winter 2027–2028 program is built around experiences that feel personal and unhurried. Guests might:

• Dive straight into turquoise water from the ship’s marina platform.
• Join a beach barbecue under the stars.
• Stay ashore late into the evening, when most larger ships and day‑trippers have gone.

Expert‑led components—such as narrated Panama Canal transits, wildlife‑focused itineraries and multi‑day overland journeys to Machu Picchu, Angkor Wat and Hanoi—add depth and context, turning each voyage into a layered story rather than a checklist of ports.

How to book Windstar’s Winter 2027–2028 cruises

Winter 2027–2028 voyages are on sale now, with the Early Booking Offer available on select sailings until April 30, 2026. Booking early gives you:

• The best fares of the season.
• First pick of suites and staterooms.
• Extra value via All‑Inclusive perks, onboard credit and a potential 5% pay‑in‑full savings.

Travellers can book online at windstarcruises.com, through a preferred travel advisor, by calling Windstar directly, or by requesting a call from a Windstar vacation planner.