Windstar Cruises unveils its 2026/27 sailings to the Caribbean and Latin America

• Windstar’s Star Seeker will also debut in the Caribbean in 2026.
• Guests have a choice of 35 sailings in the Caribbean and Latin America.
• New shore excursions will also be introduced including rum tasting in Puerto Piata.

Windstar has unveiled 35 sailings for its winter 2026/27 to the Caribbean and Latin America.

Windstar’s Star Seeker will also debut in the Caribbean in 2026.

“Windstar offers a quieter, more intimate take on the Caribbean, visiting smaller islands that larger ships can’t access – from the unspoiled beaches and coral reefs of the Grenadines to the French flair and Creole culture of Guadeloupe,” said Michele Hanson, product development manager of Windstar Cruises.

With the 10 different itineraries to be launched in 2026/27, Windstar will offer the most extensive collection of Caribbean and Latin American itineraries in its history.

The line’s flagship sailing ship, Wind Surf, will offer a seven-night Remote Caribbean Getaway and a seven-night Classic Caribbean itinerary.

Star Pride will offer weekly itineraries which will alternate between a seven-night San Juan and Virgin Islands journey and a seven-night Windward Islands Surf & Sunsets.

Star Legend will offer two sailings from Barbados in Novembers and December 2026.

Windstar will also introduce new shore excursions taking guests to rum tasting in Puerto Piata, snorkeling at Horseshoe Reef in the Tobago Cays and French creole cooking class in Marigot.

Guests will also be able to combine Machu Picchu package with its seven-night Costa Rica and Panama Canal itinerary.

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