Windstar Cruises expands 2026-27 Caribbean itineraries

Published on Aug 29, 2025, 2:39 pm CDT

6 min read

Windstar Cruises will mount its most ambitious Caribbean and Latin America season in winter 2026-27, rolling out 35 sailings across 10 itineraries on four small ships. Highlights include daylight Panama Canal transits with expert narration, first time shore excursions, and a new Cruise Tour pairing the line's seven night Costa Rica and Panama Canal itinerary with Machu Picchu. The season also features the Caribbean debut of the new Star Seeker, adding capacity on popular weeklong routes.

Key Points

Why it matters: More small-ship options to reach off the beaten path islands and Latin America highlights.
Travel impact: Weekly seven night Caribbean choices November through March from San Juan, Sint Maarten, or both, plus Canal and Costa Rica combos.
What's next: Early booking incentives run through October 31, with added onboard credits and a pay in full discount.
New experiences include rum tastings in Puerto Plata, mangrove cave boat tours in Samaná, and Creole cooking classes in Marigot.
Latin America calls span the San Blas Islands, Cartagena, Bocas del Toro, and Manuel Antonio National Park.

Snapshot

Across the region, Windstar will alternate classic and remote island routes, calling at small harbors like Anguilla, Jost Van Dyke, Virgin Gorda, Mayreau, St. Kitts, and Guadeloupe. The flagship sailing yacht Wind Surf rotates between two seven night programs from December through March, while Star Pride operates weekly from San Juan with Virgin Islands and Windward Islands variations. In Latin America, select voyages feature narrated, daylight Canal transits that feel like a river cruise for the day. New excursions range from snorkeling Horseshoe Reef in the Tobago Cays to cooking alongside a local chef in Marigot. For extended journeys, 22 Star Collector options combine multiple itineraries, offering added sea days and included laundry.

Background

Windstar's positioning centers on small-ship access, typically 150 to 350 guests, with marina platforms for water sports and beach barbecue experiences. The fleet includes three all suite Star Class motor yachts and three Wind Class sailing yachts, with a phased redesign of the sailing ships slated to finish by 2027. Star Seeker joins in December 2025, and sister Star Explorer follows in 2026, expanding deployment flexibility across the Caribbean, Costa Rica and Panama, and beyond. For the 2026-27 season, the line emphasizes quieter islands and culture forward shore time, supported by new tours and Cruise Tours. The Machu Picchu add on wraps a half day guided visit, roundtrip Vistadome train, and time in UNESCO listed Cusco around a seven night Costa Rica and Panama Canal cruise, providing a fly cruise land and sea pairing in a single booking.

Latest Developments

Star Seeker joins Caribbean lineup in 2026

Star Seeker will sail the Caribbean in winter 2026, adding berth inventory and schedule flexibility on weeklong programs from November through March. The program gives travelers a consistent cadence of seven night small-ship Caribbean itineraries from San Juan, Sint Maarten, or both, with repeat calls in the British Virgin Islands for marina days and beach barbecues. Alternating patterns allow for variety without sacrificing convenient durations, a strategy that caters to repeat guests who want new combinations of familiar favorites. Meanwhile, Wind Surf alternates Classic Caribbean with Beach Fun and Sun, showing off both marquee ports and lesser known anchorages. Together, the four ship slate broadens access to high demand islands where larger ships cannot call regularly, while maintaining Windstar's low key onboard atmosphere and water sports focus.

New shore excursions and a Machu Picchu Cruise Tour

Windstar's new tours spotlight local flavor and natural settings. Travelers can sample rums in Puerto Plata, drift by boat through the caves and mangroves of Samaná's Los Haitises National Park, and snorkel the Tobago Cays' Horseshoe Reef. A French Creole cooking and mixology class in Marigot adds culinary depth to the Leewards. Southbound, Latin America itineraries bring daylight Canal transits narrated by onboard experts, plus calls at the San Blas Islands, Cartagena's walled Old Town, Bocas del Toro, and Costa Rica's Manuel Antonio National Park. The new five night pre or post Cruise Tour adds Machu Picchu via the Vistadome train, a guided site visit, and UNESCO listed Cusco, creating an efficient land and sea package linked to the seven night Costa Rica and Panama Canal voyage.

Windstar Cruises Caribbean itineraries, at a glance

Beyond weeklong options, 22 Star Collector voyages stitch together multiple itineraries, including a new 16 night Latin American Explorer and a 70 night Grand Star Collector from Istanbul to Costa Rica. Collectors include laundry service and more sea days, a value add for travelers seeking deeper immersion. Early bookers can reserve by October 31 for the best published fares and up to $200.00 in onboard credit, and may save an additional 5 percent by paying in full with code PIF. The line's All In package, valued at $99.00 per person per day, bundles gratuities, Wi Fi, and select alcoholic beverages, simplifying budgeting. With fleet growth and refreshed sailing yachts, the 2026-27 season marks Windstar's broadest Caribbean and Latin America deployment to date.

Analysis

Windstar's 2026-27 plan doubles down on what small-ship loyalists value, namely variety on seven night runs, access to petite harbors, and relaxed onboard pacing. Weekly combinations from San Juan and Sint Maarten keep lift and hotel planning straightforward, while alternating patterns refresh the experience for repeaters. That is important in the Caribbean, where seasoned cruisers often chase new islands rather than new ships. The daylight, narrated Canal transits sharpen differentiation versus big-ship partial crossings, effectively turning a sea day into a guided program without crowding.

On the commercial side, adding Star Seeker raises peak season capacity without straining port access, since the brand continues to target sub 350 guest vessels. The Cruise Tour to Machu Picchu is savvy packaging, converting a bucket list land experience into incremental cruise revenue and offering a clear reason to book direct or with an advisor. New shore excursions align with demand for culture and nature, from Creole cooking to protected mangrove habitats, reinforcing the brand's service-oriented positioning rather than chasing onboard spectacle. The early booking stack, onboard credit plus a pay in full discount, should pull yield forward while rewarding planners who commit before competing lines release late season promos. Net, the itinerary map looks both broader and tighter, expanding choice while preserving Windstar's small-ship DNA.

Final Thoughts

For travelers who prefer intimate ships, marina days, and long hours ashore, Windstar's winter map offers a practical balance of convenience and discovery. The weekly seven night cadence fits typical vacation windows, and the Cruise Tour adds a seamless path to Machu Picchu without a separate trip. With new excursions, narrated Canal crossings, and the arrival of Star Seeker, the 2026-27 season underscores the brand's commitment to small-harbor Caribbean and Latin America access. If you want fewer crowds, more water time, and a relaxed onboard vibe, this is a timely moment to explore Windstar Cruises Caribbean itineraries.