Year-Round Sun & Yacht-Style Fun
Explore exclusive yachting harbours in the Caribbean and Latin America.
The tropics offer more than sun and sea — though there’s plenty of that too. With Windstar, they become a gateway to something rare.
Our 2026 and 2027 Caribbean and Latin America voyages reveal a side of these regions few travelers ever see, combining moments like a daylight Panama Canal transit and a sunset sail past St. Lucia’s Pitons with access to small yachting harbors like St. Barts and the protected San Blas Islands.
Explore The Baths’ cathedral-like grottoes in Virgin Gorda, transit the Panama Canal with an expert at your side or paddle straight off the Marina at the back of your yacht.
This season, our newly refreshed 342-guest Wind Surf returns to the Caribbean with two alternating itineraries. Choose Beach Fun & Sun: A Remote Caribbean Getaway for a relaxed escape to quiet favorites like Anguilla and St. John — or go classic with a call at legendary St. Barts and visits to St. Kitts and St. Lucia.
Looking for something beyond the usual beach break? Our Panama Canal, Cartagena, San Blas Island & More voyage offers rainforest adventure and rare cultural connection. Visit the San Blas Islands, home to the Guna Yala people, and explore Costa Rica’s lush coastlines with insight from onboard naturalists.
Reserve by October 31 to take advantage of the best fares we will ever offer for these voyages — and enjoy up to $200 in onboard credit and an All-Inclusive experience — featuring Wi-Fi, unlimited select wine, beer and cocktails, and gratuities.
New! Pay Now, Save More. Save 5% on these newly released voyages with booking code PIF when you pay in full at the time of booking.
