From $ 2,999 pp
departure date

14-day Caribbean Collection

From $ 2,999 pp

Bridgetown to Bridgetown

14-day Caribbean cruise Collection
Enjoy two weeks indulging in the yachting lifestyle as you explore new ports each day throughout the delectable Leeward and Windward Islands from either Barbados or St. Maarten. Visit more enticing places with no repeat ports over the course of your voyage, and stay late into the evenings allowing for in-depth adventures. Point the bow to yachting favorites like Pigeon Island, St. George’s, and Bequia. Go places that appear on very few Caribbean cruise itineraries like the modern-day Pompeii of Montserrat. Enjoy Windstar's exclusive Signature Beach Barbecue at Prickly Pear Beach on Virgin Gorda, where mangroves and hiking trails augment the pristine beaches of this National Park.

Thank You!

We'll send you the latest deals to your email.

Click here to view our current special offers.