|

Windstar Cruises Expands 2026-27 Caribbean and Latin America Voyages

ByHarrison Liu

Windstar Cruises has unveiled what it claims as its biggest-ever Caribbean and Latin America program for the 2026-2027 winter season. The small-ship cruise line will offer 35 voyages across 10 itineraries.

Star Pride calls at Willemstad, Curaçao.
Star Pride calls at Willemstad, Curaçao. Image courtesy of Windstar Cruises.

A highlight of the season is the debut of Star Seeker in the Caribbean in winter 2026. The new yacht joins Windstar’s boutique fleet of sailing and all-suite ships.

“Windstar offers a quieter, more intimate take on the Caribbean, visiting smaller islands that larger ships can’t access,” said Michele Hanson, product development manager at Windstar Cruises.

Sea days have a different meaning on Windstar's small ships.
Sea days have a different meaning on Windstar’s Wind Surf. Image courtesy of Windstar Cruises.

Passengers can use the line’s popular Watersports Marina, which opens directly into the sea for swimming, kayaking, paddleboarding, and snorkeling.

Caribbean Highlights

From November through March, Windstar will offer weeklong cruises departing from San Juan and St. Maarten. Passengers can sail into Anguilla, Jost Van Dyke, and Virgin Gorda, where the line hosts its popular beach barbecues.

Prickly Pear, Anguilla, is one Windstar’s signature, beach-barbecue sites on a Caribbean voyage. Image courtesy of Windstar Cruises.

New excursions include rum tastings in Puerto Plata, snorkeling in the Tobago Cays, and a French Creole cooking class in Guadeloupe.

Latin America Adventures

Windstar is also expanding in Latin America. A new land package pairs the 7-night Costa Rica & Panama Canal voyage with a 5-night trip to Machu Picchu and Cusco.

Other highlights include daylight Panama Canal transits narrated by experts, visits to the San Blas Islands and Bocas del Toro, and wildlife encounters in Costa Rica’s Manuel Antonio National Park.

Longer Voyages

For extended travel, Windstar is expanding its Star Collector series. Options include a 16-night Latin American Explorer and a 70-night Grand Star Collector from Istanbul to Costa Rica. These longer trips include complimentary laundry and deeper cultural immersion.

Booking Offers

Travelers who book early can save 5% by paying in full. Additional perks include up to $200 in onboard credit and Windstar’s All-Inclusive package with Wi-Fi, gratuities, and select beverages.

With more ships, more itineraries, and new land-and-sea combinations, Windstar’s 2026-2027 season promises its most ambitious collection yet. The program highlights the Caribbean and Latin America as only small-ship cruising can.

Similar Posts