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If you are dreaming of warm seas, small harbours, and days that balance exploring with proper downtime, the latest deployment from Windstar Cruises is right in your sweet spot. The line has unveiled its most extensive winter schedule yet across the Caribbean and Latin America, pairing small-ship access with thoughtful shore days and new overland extensions. Below, we unpack what is new, why these itineraries feel different, and how to match a sailing to your travel style.
What Windstar Is Rolling Out for 2026 to 2027
The upcoming winter season is Windstar’s biggest warm-weather push to date. It blends headline moments, like daylight transits of the Panama Canal, with the quieter joys of anchoring off postcard coves that bigger ships skip. Think rum tastings, mangrove glides, and reef time, then add curated land stays that take you deep inland before or after you sail.
New Capacity with Star Seeker
Star Seeker joins the fleet in late 2026, giving Windstar fresh capacity in the Caribbean at exactly the time demand spikes for sun, sea, and smaller crowds. The ship’s arrival unlocks more choices across weeklong loops and longer combinations, and it keeps the small-yacht vibe that defines the brand.
With more berths but the same intimate scale, guests gain options without losing that relaxed, clubby atmosphere on deck.
Ten Itineraries Across 35 Sailings
From November through March, the programme covers 35 departures across ten distinct routes. You will see classic seven-night circuits from San Juan and St. Maarten, plus late-2026 Barbados starts before repositioning to Latin America. This variety matters, since it lets you align ports and travel dates without compromising on the small-ship feel.
Smaller Ports, Bigger Stories
The flagship Wind Surf will alternate between two seven-night routes, one that leans into remote islands and beaches, another that hits marquee Caribbean names. Star Pride mirrors the rhythm from San Juan, while Star Legend branches south, calling in places most ships cannot reach. The common thread is size. These yachts slip into sheltered bays and compact harbours, which means tender rides to tiny towns, quiet snorkel spots, and local eateries where the cook knows the fisherman by name.
First-Time And Fresh-Look Excursions
New shore days add texture. Guests can try rum tastings in Puerto Plata, glide by boat through the mangroves and caves of Haitises National Park in Samaná, snorkel Horseshoe Reef in the Tobago Cays, or roll up sleeves for a Creole cooking and mixology class in Marigot. They are the sort of experiences that pair nicely with an afternoon sailaway and a sunset on the top deck.
Caribbean Highlights You Will Not Find on Big Ships
Windstar’s Caribbean has always been about access. The joy here is not a theme park slide or a megaship promenade, it is docking or anchoring close to where island life hums along, then returning to a yacht that still feels unhurried at cocktail hour.
Remote Islands on Weeklong Loops
Those seven-night loops from San Juan and St. Maarten give you the greatest hit list of hidden harbours. Remote anchorages and beach days are built in, so you might spend the morning wandering a market in a port few people can point to on a map, then be back on board for a late lunch before a swim from the marina platform. It is a rhythm that suits travellers who want to move often without feeling rushed.
Signature Shore Days, From Rum to Reefs
The new excursions read like a tasting menu of the region. Rum in Puerto Plata makes cultural sense, since the spirit touches agriculture, trade, and daily life. The Haitises mangrove and cave tour is a gentle way to see coastal ecosystems up close, and Horseshoe Reef in the Tobago Cays is a Swiss-army-knife snorkel day, alive with coral, rays, and turtles. A Marigot class in Creole flavours ties cuisine to history, which is exactly the kind of detail that sticks with you long after the holiday.
Why San Juan and St. Maarten Matter
As gateways, San Juan and St. Maarten keep flights straightforward from Australia via the US or through major hubs for international guests, and they also frame the islands around them. Starting in San Juan adds a dose of Old World Spanish charm and easy pre-cruise wandering within the forts and cobbled lanes. St. Maarten opens a door to both Dutch and French flavours in one tiny dot on the map, which is a fun contrast before you fan out to smaller islands.
Latin America with Daylight, Depth, and Choice
South of the islands, Windstar leans into daylight transits, national parks, and cultural pairings. The pacing remains relaxed, but there is more emphasis on wildlife, landscapes, and overland connections that turn a voyage into a broader journey.
Panama Canal in Daylight with Expert Commentary
Daylight transits of the Panama Canal are a smart move. You actually see the locks fill and fall, and onboard experts talk through the engineering and history as it happens. It is not just a tick-box experience, it is a day of learning and photography that turns a single line on a map into a living story. The commentary helps first-timers and canal veterans alike notice the details they would otherwise miss.
Costa Rica’s National Parks and Mangroves
Costa Rica itineraries focus on national parks, mangrove tours, and coastal catamaran sailing. You might kayak quietly under a canopy while spotting herons and monkeys, then switch gears for a lazy sail along a beach-dotted shoreline. It is all very nature-forward, perfect for travellers who prefer binoculars and walking shoes to shopping bags.
Cartagena, San Blas and Bocas del Toro
Some Latin America routes pair the walled city of Cartagena with the San Blas Islands and Bocas del Toro. That means a UNESCO-listed old town at one end, then a swing through island chains known for palm-hung beaches and clear water. It is a blend of history, colour, and beach life that rewards both photographers and swimmers.
Linking Machu Picchu to Sea Days
New land programmes link Machu Picchu with Costa Rica and Panama Canal sailings. Guided time at the site, a Vistadome train journey, and a visit to Cusco give you a high-altitude counterpoint to jungle and coast. If you have long wanted to pair Andean history with tropical shore days, this is your chance to stitch them together without juggling multiple operators.
Who These Voyages Suit and How to Book Smart
With four yachts in play and a mix of weeklong and extended runs, this is a choose-your-own-adventure season. The trick is to match the ship and route to how you like to travel, then consider whether a longer combination will save you a flight or two.
Time Poor Travellers and New to Cruise Guests
If you only have a week and want to test small-ship life, pick a seven-night Caribbean loop from San Juan or St. Maarten. The sailing pace is easy, the ports are compact, and you still get that big-holiday feeling. New to cruise guests often love the balance, since you unpack once and wake up somewhere fresh without constant logistics.
Wildlife Lovers and Culture Seekers
Choose Costa Rica and Panama Canal routes if you want birds, beaches, and boat-through-mangroves moments. Add the Machu Picchu extension if you are keen on archaeology and altitude. For a history-and-harbour mix, the Cartagena routes with San Blas and Bocas del Toro deliver story and snorkel in the same trip.
Couples, Friends, and Families
Windstar’s small-ship vibe suits couples who like long dinners and stargazing, friends who enjoy active shore days, and families with adult children who want more nature than nightlife. The new Star Seeker capacity means more date options around school and work calendars, which makes planning simpler for mixed groups.
Should You Pick a Star Collector Voyage
Longer Star Collector combinations stitch multiple itineraries into one seamless trip. Highlights include a 16-night Latin American Explorer and a 70-night Grand Star Collector epic from Istanbul to Costa Rica. These are for travellers who want deep immersion, fewer flights, and the satisfaction of watching a map unfold day by day. If you have the time, they offer superb value in experience per kilometre.
Now, if you are weighing two similar routes or timing a canal transit for the driest months, that is where a specialist helps. We can map your preferred ports against wildlife windows, festivals, and flight patterns, then recommend the yacht that fits your pace.
Short of time or juggling school holidays? Start with seven nights and a focused set of ports. Looking to make 2027 the big one? Add Machu Picchu and a canal day, then finish with a beach-heavy Caribbean loop.
If the idea of browsing exact dates and matching ships to your calendar sounds good, head straight to our Cruise Finder. It is the fastest way to see which Windstar itineraries align with your preferred month and must-see ports. Prefer a human to parse the finer points like balcony orientation or which yacht has the quieter observation nook? We are happy to shortlist the best fits and hold a courtesy cabin while you lock in flights.
Plan Your Windstar Cruise with S.W. Black Travel
The 2026 to 2027 season shows Windstar Cruises doing what it does best, small-ship routes that get you closer to the good stuff, plus meaningful overland links that turn a voyage into a full journey. If warm seas, compact harbours, and daylight canal stories are calling, let us put the pieces together. Start the conversation and plan your Windstar holiday with our team now.
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