Windstar Cruises launches Caribbean and Latin America 2026/27 season

Windstar Cruises has launched 13 itineraries for its Caribbean and Latin America season for 2026 and 2027.

The 148-passenger Wind Star and 312-passenger Star Pride will operate the sailings in the region.

The 18-day Star Collector: Reefs & Rainforests and seven-day Costa Rica & Panama Canal itineraries will return for the season on Wind Star.

Wind Star will also sail a 25-night Southern Caribbean Thanksgiving Jubilee on November 10, 2026, from Lisbon crossing to Barbados and cruising the Caribbean before heading to Colombia and Panama.

Prices start from £2,301 per person for a seven-night Windward Islands Surf & Sunsets sailing departing on January 3, 2027, or for a seven-night San Juan & the Virgin Islands sailing departing January 10, 2027.

Both cruises are round trip San Juan on Star Pride and are inclusive of all meals and drinks, Wi-Fi, gratuities and port fees.

Booking these voyages before May 31 will receive a complimentary upgrade to an all-inclusive fare which includes Wi-Fi, gratuities, unlimited select beer, wine and cocktails and $200 onboard credit per stateroom.

Jess Peterson, Windstar’s director of destination experience and itinerary planning, said: “Windstar embraces a laid-back, yachting vibe in the Caribbean. We focus on relaxing beaches and the more exclusive islands such as Jost Van Dyke, St. Barths and Virgin Gorda.

“We layer on our signature experiences like a beach barbeque on a remote island and swimming from the ship’s stern platform. A small-ship Caribbean cruise is a totally different experience.”