New 2026 & 2027 Voyages

Get Closer in Private-Yacht Style

Windstar’s 2026 and 2027 voyages are open for reservation — and these seasons are all about embracing the new.

Discover new itineraries, new experiences, new destinations (and even new yachts!) across the Caribbean, Canada & New England, Japan, and Latin America.

Be one of the first to reserve your voyage and enjoy a complimentary All-Inclusive experience, featuring WiFi, unlimited select wine, beer and cocktails, and gratuities — valued at more than $1,300 per stateroom on a 7-day cruise.

Plus, enjoy an onboard credit of up to $200 per stateroom, good for shore excursions, treatments at World Spa by Windstar and other amenities.

Caribbean & Latin America: From breezy islands that big ships can’t reach and centuries-old colonial harbors to some of the world’s greatest wonders, our winter 2026 and 2027 sailing seasons bring you closer to everything that makes these regions unforgettable. Offer ends May 31, 2025.
SEE ALL VOYAGES

Grand Japan: Explore the land of the rising sun with Star Seeker, Windstar’s new 224-guest yacht — where every room is an ocean-view suite. Take advantage of newly released sailing dates starting October 2026 through spring of 2027 during cherry blossom season. Offer ends February 28, 2025. SEE ALL VOYAGES

Canada & New England: Discover new worlds closer to home with our 2026 voyages in Canada and New England. Experience the stunning beauty of Greenland, explore the only French territory left in North America and much more. Offer ends April 30, 2025. SEE ALL VOYAGES

See terms and conditions

Make Plans To Cruise
Mount Fuji - Enjoy panoramic views of Mount Fuji, an iconic World Heritage Site.
Japan Cruise Tour - Combine your Japan voyage with an inland Cruise Tour of Kyoto and Osaka.
The neighborhood of Old Quebec is home to the only fortified city walls north of Mexico.
With a history dating back over 500 years, St. Johns is one of the oldest European-founded cities in North America.
Get a firsthand look at Costa Rica’s astounding biodiversity with a guided tour of Manuel Antonio National Park.
Visit the Baths of Virgin Gorda — a series of granite boulders sculpted by the sea into natural pools and grottoes.
Filter Results
Showing 300 of 300 voyages from this special
CLEAR FILTER SELECTIONS
Sort:
Destination
Ship
Dates
Duration