Windstar Cruises is offering a limited-time “Ways to Winter” promotion from September 25 through October 7, 2025. The offer features a free all-inclusive package and 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.
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.
The “Ways to Winter” offer includes Windstar’s All-In Package, which covers unlimited Wi-Fi; onboard gratuities; a wide selection of beer, wine and cocktails; and up to $1,000 onboard credit for guests to personalize their voyage with curated shore excursions, spa indulgences or other onboard amenities.
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. Destinations include:
- 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.
- 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.
- 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.
Other regions included in this limited-time promotion range from Greece to Northern Europe, South America and classic “Ocean Crossings,” all selected for their distinctive seasonal allure and immersive cultural experiences.
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