New Adventures with Windstar Cruises in the Caribbean and Latin America

Windstar Cruises Unveils New Itineraries for Winter 2026/2027

Windstar Cruises has announced a sweeping expansion of its offerings for the winter 2026/2027 season, featuring a total of 35 sailings spread across 10 new itineraries in the Caribbean and Latin America. Highlighting these adventures are unique daylight transits of the Panama Canal along with a variety of new shore excursions tailored to enhance the guest experience.

Expanded Itineraries

This updated schedule, which introduces the debut of the Star Seeker in Caribbean waters, is designed for performance with four yacht-style ships ensuring a personal and intimate cruising atmosphere. Actively serving the itineraries from November through March, certain departures are available from the picturesque locales of San Juan and San Maarten. The itineraries promise visits to charming smaller ports such as Anguilla and Jost Van Dyke, destinations often unreachable by larger vessels.

Unique Shore Excursions

Guests can look forward to engaging activities such as snorkeling at Prickly Pear, zip-lining through lush jungles in St. Kitts, and enjoying a Signature Beach Barbecue in idyllic sites like Virgin Gorda and Mayreau. Numerous itineraries will feature Windstar's Watersports Marina, allowing guests to take part in various water sports right from the ship.

Beach Fun & Classic Caribbean Itineraries

The Wind Surf, recognized as the flagship sailing ship of Windstar, will alternate between two captivating 7-night itineraries titled "Beach Fun & Sun: A Remote Caribbean Getaway" and "Classic Caribbean." Key features of these voyages make them a delightful option for beach lovers and adventure seekers alike.

Latin American Highlights

Windstar has also curated a selection of Latin America itineraries, including an exciting cruise tour that combines an unforgettable visit to Machu Picchu with the "Costa Rica & Panama Canal" itinerary. This package allows travelers to immerse themselves in the Wonders of the World, paired with enlightening tours of the UNESCO World Heritage location in Cusco. Through expert guidance, guests can appreciate the breathtaking daylight transits of the Panama Canal.

Exploring Unique Destinations

Key routes through Latin America will be covered by the Star Legend, Wind Star, and Star Pride, showcasing captivating destinations like the San Blas Islands and the historic city of Cartagena. The "Naturally Costa Rica" voyages will delve into scenic views of Manuel Antonio National Park, with opportunities for guided boat tours through mangroves and explorations of local wildlife.

Special Offering: Star Collector Voyages

In a bid to cater to the more adventurous travelers looking for extended journeys, Windstar has introduced a series of 22 Star Collector voyages. These combine multiple itineraries into longer sailings, providing additional days at sea while opening the doors to enriching cultural experiences.

Booking Details

The new itineraries are now officially available for booking, complete with early booking offers valid until October 31. This is an excellent opportunity for travelers seeking unique experiences in the stunning landscapes of the Caribbean and Latin America.

A Glimpse into the History of Cruising

The cruising industry has transformed significantly over the decades. Initially regarded as a luxury reserved for a select few, cruising has evolved into a mainstream holiday option appealing to a diverse audience. Since the 1980s, passenger numbers have soared due to expanded marketing and improved vessel capacity. The Caribbean, in particular, stands out as the premier cruise destination globally, favored for its proximity and warm climate.

The Growth of the Caribbean Tourism Sector

Today, a large part of Caribbean tourism is driven by cruises, with the region hosting a variety of cruiser-friendly infrastructures and inviting shore activities. As the market for cruising continues to grow, small islands that were once sidelined are now experiencing a significant uptick in tourist activity, highlighting the essential role of sailing in the regional tourism narrative. It’s intriguing to note that larger ships are often unable to access these smaller, charming ports, making yacht-based travel an attractive alternative for visitors.

Future of Tourism in Caribbean and Latin America

As global tourism evolves, the Caribbean and Latin America remain at the forefront, attracting visitors with their unique cultures, stunning natural beauty, and rich history. This region's accessibility and the variety of cultural and recreational experiences available ensure its standing as a favored destination for leisure travelers.

Windstar Cruises’ latest offerings are a testament to the continuing allure of this vibrant region. Those looking for an adventurous way to explore the Caribbean and Latin America while enjoying the luxury of yacht-style cruising will find ample opportunities ahead.

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