Explore the Caribbean with Windstar Cruises

Windstar Caribbean cruise ships

Although some areas of the Caribbean are rebuilding after the recent hurricanes, the majority of the Caribbean is open and welcoming visitors to their wondrous islands. Windstar is launching their upcoming Caribbean season that will set sail from Bridgetown in Barbados and San Juan in Puerto Rico. While Barbados was spared any damage in the storms, San Juan has been working to make repairs, and day by day, more hotels, restaurants and stores are welcoming customers back to this beautiful location. The San Juan Airport is fully operational with 70 flights a day and the cruise port has had more than 5,000 passengers in the last two weeks.

To welcome Windstar’s guests back to the Caribbean, we’re offering a special Caribbean Is Open Cruise Package full of additional perks and savings on all 2017 Caribbean sailings. Enjoy extraordinary cruise pricing, $200 shipboard credit, and free onboard Wi-Fi for posting all those envy-inducing vacation photos.

These cruise packages include:

  • Ocean view stateroom or suite aboard Windstar’s all-suite or sailing ship
  • USD$200 shipboard credit for each guest
  • Wi-fi access
  • All non-alcoholic beverages
  • Watersports platform with kayaks, stand up paddle boards, water trampoline and more
  • Champagne welcome reception

Hurry and book today before these cruises sell out!

Upcoming Sailings


Bridgetown . Little Bay . Basseterre . Les Saintes . Anse Mitan . Pigeon Island . Bridgetown . Anse Mitan . Pigeon Island . St. George’s . Bequia . Mayreau . Bridgetown

Sailing dates:   12/16/17, 12/23/17, 12/30/17
From $2,399 pp $200 shipboard credit + free wi-fi


Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.


San Juan . Anse Mitan . Pigeon Island . Les Saintes . Little Bay . Gustavia . San Juan

Sailing dates:   12/02/17, 12/09/17, 12/16/17
From $999 pp $200 shipboard credit + free wi-fi


Begin and end your journey on this bewitching Caribbean cruise, where no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages on this Caribbean cruise.


Bridgetown . Little Bay . Basseterre . Les Saintes . Anse Mitan . Pigeon Island . Bridgetown

Sailing dates:   12/09/17, 12/23/17
From $ 1,099 pp $200 shipboard credit + free wi-fi


From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.


 San Juan . Basseterre . Gustavia . Falmouth Harbour . Les Saintes . Pigeon Island . St. George’s . Bequia . Anse Mitan . San Juan

Sailing dates:   12/23/17
From $ 1,799 pp $200 shipboard credit + free wi-fi


By departing from magical San Juan instead of from Florida, your Caribbean cruise vacation begins earlier, on day one. And with 11 days instead of the usual 7, you have time to take the full measure of this most iconic parts of the Caribbean. Everywhere you look is another cover shot image. Dazzling white sand turns the shallows mesmerizing shades of peacock and mermaid, weathered fortresses point canons at long-vanished schooners, natural pools warm gently under the mid-day sun. On your privateship, you’re equally at home in exclusive harbors and anchored off barefoot beaches, so you can see it all. Snorkel or dive on vibrant coral reefs. Follow your siren inland to rainforest adventures or duty-free boutiques. Thank your lucky Star Pride for bringing you here.


 Bridgetown . Anse Mitan .  Pigeon Island . St. George’s . Bequia . Mayreau . Bridgetown

Sailing dates:   12/16/17, 12/30/17
From $ 1,099 pp $200 shipboard credit + free wi-fi


This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.