Cruise Beyond in the Caribbean

Ready to discover the Caribbean that feels refreshingly new? Make your way to the secluded sands and lesser-known corners of the tropics as we bring back favorites and introduce all-new voyages for 2027 and 2028.

From the natural wonders of the British Virgin Islands to the perfect relaxation of St. Barts, you’ll sail far from the routine to experience a different side of the Caribbean.

What Does It Mean to Cruise Beyond in the Caribbean?

It means waking up, enjoying a lovely breakfast on board and then jumping into the most exquisite pool on earth — the Caribbean Sea — directly from the onboard Marina on your yacht.

Or veering from the routine to dig up treasures only a small ship can find. Snorkel the mysterious rock formations of the Baths in Virgin Gorda. Raise a rum drink at Foxy’s, a favorite watering hole for sailors who drop anchor at Jost Van Dyke. Or embark on a new sailing to the ABC islands (Aruba, Bonaire and Curaçao).

Uncrowded. Unspoiled. Unforgettable. This is the Caribbean waiting for you on every Windstar voyage.

Even Our Offer Goes Beyond 

Book a newly released 2027 and 2028 cruise by April 30, 2026, and take advantage of the best values we’ll ever offer on these voyages — plus: 

• Complimentary All-Inclusive package — Wi-Fi, gratuities, and unlimited cocktails, wine by the glass and beer.

• $100 onboard credit per guest.

• 5% savings on cruise fares when you pay in full at time of booking.

See Terms and Conditions.