Windstar Launches 'Ways to Winter' Promotion

Credit: Windstar Cruises

(Press Releases) MIAMI, FL, September 25, 2025 – As last-minute travel continues to surge, Windstar Cruises invites travelers to turn winter on its head and experience the season like never before. From September 25th through October 7, 2025, Windstar is offering a limited-time Ways to Winter promotion featuring a Free All-Inclusive Package plus up to $1,000 onboard credit per stateroom on select small ship cruises in Tahiti, the Caribbean, the Mediterranean and the Canary Islands – destinations that shine brightest in the off-season. Travelers can use the offer to save and sail on voyages departing through the end of March 2026.

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Why Choose Windstar for Your Winter travels?
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Windstar Cruises’ small ships visit unique destinations that larger ships can’t reach and are best experienced in the cooler months. Off-season travel means more space, more value, and a deeper discovery with fewer crowds and a warm welcome from locals. Guests enjoy Windstar’s signature blend of casual luxury and friendly service along with seasonal experiences such as: 

• In the Mediterranean, the off-season allows travelers to explore historic cities in Spain, Italy, Croatia and France without crowds. Windstar’s yachts offer rare winter exclusives such as overnight stays in Barcelona and Livorno (Florence) and truffle-hunting excursions in Italy. 
• In the Caribbean, Windstar skips the mega-ship ports for boutique yachting harbors like Jost Van Dyke, Virgin Gorda, and St. Barts, delivering a sunny escape with a relaxed, exclusive feel. 

What Perks are Included in the Ways to Winter Offer?
The promotion includes Windstar’s All-In Package, which covers:

• Unlimited Wi-Fi for easy sharing of vacation memories
• All gratuities, making every interaction carefree
• A wide selection of beer, wine, and cocktails to toast the journey

Depending on the length of the itinerary, guests also receive up to $1,000 Onboard Credit to personalize their voyage with curated shore excursions, spa indulgences, or other onboard amenities.

When is the Promotion Available?
The offer is available to book September 25 – October 7, 2025 for voyages departing through March 2026, with a focus on winter-sun destinations perfect for escaping cold weather.

Where Can a Small Ship Cruise Take You This Winter?
Travelers can swap short days and chilly nights for sun-filled yacht adventures across some of the world’s most captivating regions, many only available in the winter. 

• Tahiti (September – March): Enjoy the quiet season in the islands. Guests can immerse themselves in island culture and swim directly from the yacht’s Marina into turquoise lagoons. Swim with reef sharks and manta rays. Drift over coral gardens. Find a black pearl. 
• Caribbean (October – March): A winter only escape: Cozy harbors with colorful beach towns and vibrant local rhythms come to life aboard an all-suite or classic sailing yacht. Snorkel and dine at the epic beach BBQ. Unwind at famous beach bars. Try local specialties like conch fritters.
• Canary Islands (November – February): Explore volcanic landscapes and Moorish influences with ease aboard a sailing yacht, a winter-only, sunny escape. Ride a wicker toboggan. Sip wine in volcanic vineyards. 
• Costa Rica & Panama Canal (November – March): Traverse the legendary canal and enjoy the lush rainforest and beaches in comfort and style. Monkeys, toucans and sloths. Eye-level daylight transit of the Panama Canal. Only available in winter.
• Mediterranean (October – March): Iconic ports and local traditions shine during the quieter, more intimate winter season with cruises exploring Spain, Italy, France and Croatia. Festive Christmas markets shine. Easy access to historical sights. Overnights to spend more time exploring ashore. 

Other included regions range from Greece to Northern Europe, South America, and classic Ocean Crossings, all selected for their distinctive seasonal allure and immersive cultural experiences. 

“We’re experiencing incredible momentum, particularly for short-lead travel,” says Dianna Rom, vice president of sales at Windstar Cruises. “This promotion encourages guests and travel advisors to book now by offering added amenities and incentives to try something new.  It’s a jump on Wave Season, and the time to act is now.”

What Do Travelers Need to Know?

• Booking window: September 25 – October 7, 2025
• Eligible voyages: Departures through March 2026
• Free All-Inclusive Upgrade: Typically a $99 per person, per day value; includes Wi-Fi, all gratuities, and select beer, wine, and cocktails & complements Windstar’s always-included extras like 24-hour room service, specialty dining, complimentary water sports from the yacht’s marina and destination-focused programming.
• Best Suite Selection: Booking early ensures access to the most desirable suites.
• See Terms & Conditions here
• Save Big with Our Xanterra Sister Brands: From awe-inspiring national park stays to unforgettable biking adventures, and more, now is the time to save big on your next unforgettable adventure. Explore offers here. 

How to Book: To plan a small ship cruise with Windstar book online here, contact a travel advisor, reach out to Windstar Cruises by phone at 866-258-7245, or request a call by a Windstar vacation planner.