Hold times may be longer than usual: We're currently undergoing a reservation system upgrade and are still fixing some issues. Please contact us if you have any questions.

Thankful for Travel To The Caribbean

Pick Your Perk for a Caribbean Cruise and Save

The Caribbean’s 700 islands boast rainforests, sparkling beaches, diverse cultures, and more, but you don’t have to puzzle through which islands to visit in order to experience it all. Windstar’s small ships know the way to the best islands, with small-group excursions curated by our experts that immerse you in a meaningful way.

Jump directly into the warm tropical ocean from your yacht’s Watersports Platform to swim, paddleboard, and kayak. Mingle among new friends at our Signature Onboard Barbecue. Dance with the wind at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing. You’ve slowed down to a Windstar pace of life, and that’s a good thing.
 

During our 2023 Thankful for Travel Sale, you’ll be able to enjoy more of the Caribbean, for less when you Pick the Perk you like best. Here’s what you can enjoy when you Pick Your Perk:

  • One free pre- or post-cruise hotel stay OR
  • Up to $1,000 onboard credit, OR
  • Premium Suite guests may select a free upgrade to an All-Inclusive Fare featuring Wi-Fi; unlimited beer, wine & cocktails; and all gratuities.

PLUS all guests can enjoy a reduced deposit of just 5%.



*Premium Suites include Owner's Suite, Classic Suite, and Deluxe Suite. Terms and Conditions apply.

Small Ships, Big Opportunities
Our award-winning, small yachts are practically built for the Caribbean’s intimate coves and hidden harbors, and can easily access white sand beaches and tiny oceanside towns. Our ships boast multiple dining venues and renowned culinary masters — drawn to Windstar in part because we’re the Official Cruise Line of the James Beard Foundation.

Choose Your Adventure
With so many remarkable islands to choose from, we offer numerous itineraries so you can see as much of the Caribbean as you wish. Enjoy a short five-day getaway in the British Virgin Islands that will leave you long on memories. Take a just-long-enough-to-unwind 10-day cruise of the Leeward Islands about our four-masted sailing ship, Wind Spirit. Or go all in on adventure on our 55-day Star Collector: Grand Caribbean Adventure cruise that visits 28 islands and 33 ports. No matter where in the Caribbean you choose to sail, adventures 180 degrees from ordinary wait for you with Windstar.

More to be Thankful For
When it comes to travel, there’s so much to be grateful for. Discover the details of this limited-time sale and all of the great offers from our sister companies that are part of Xanterra Travel Collection®. A World of Unforgettable Experiences® is just a click away.

SEE ALL VOYAGES