Windstar launches “Ways to Winter” promotion with all-inclusive perks

Windstar Cruises has announced a limited-time “Ways to Winter” promotion offering a free All-Inclusive Package plus up to $1,000 onboard credit per stateroom on select small-ship sailings. 

The offer is available to book from September 25 to October 7, 2025 on voyages departing through March 2026 across destinations such as Tahiti, the Caribbean, the Mediterranean and the Canary Islands.

The All-Inclusive Package covers unlimited Wi-Fi, all gratuities and a selection of beer, wine and cocktails. 

Guests also receive up to $1,000 in onboard credit, depending on itinerary length, to use toward shore excursions, spa treatments or other onboard options.

Winter itineraries

Windstar’s small ships visit harbours and ports often inaccessible to larger vessels, with itineraries tailored to off-season travel:

• Tahiti (Sept – March): Quieter lagoons and direct water access from the ship’s marina, plus chances to snorkel with reef sharks and manta rays or explore coral gardens.
• Caribbean (Oct – March): Smaller ports such as Jost Van Dyke, Virgin Gorda and St. Barts, beach bar stops and onboard events like a beach barbecue.
• Canary Islands (Nov – Feb): Volcanic landscapes, Moorish heritage and local wine regions, plus winter-only sailings.
• Costa Rica & Panama Canal (Nov – March): Rainforest wildlife, beaches and daytime Panama Canal transits.
• Mediterranean (Oct – March): Historic cities in Spain, Italy, France and Croatia with fewer crowds, Christmas markets and overnight stays in ports such as Barcelona and Livorno.

Other winter itineraries include Greece, Northern Europe, South America and ocean crossings.

“We’re experiencing incredible momentum, particularly for short-lead travel,” said 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.”

The booking window runs September 25 to October 7, 2025. Eligible departures extend through March 2026.

The Free All-Inclusive upgrade — normally $99 per person, per day — includes Wi-Fi, gratuities and select drinks, alongside Windstar’s standard offerings such as 24-hour room service, specialty dining, complimentary water sports and destination-focused programming.

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