If your ideal cruise looks more like a floating boutique hotel than a mega-ship resort, Windstar’s newly released winter 2027-2028 programme is going to feel like a very good kind of distraction. The headline is varied, not just in where the ships are going, but in how Windstar is shaping the season around limited-run itineraries, deeper cultural moments, and the kind of access that works best on smaller ships.
Windstar Cruises has opened bookings for the northern winter 2027-2028 with 230+ sailing dates worldwide and 21 new itineraries departing from September 2027 to April 2028. The season spans Tahiti, Asia, the Caribbean, Latin America, and the Canary Islands, including a rare one-time South Pacific crossing, yacht-style regional cruising, and select one-night Destination Discovery Events, plus inclusions such as James Beard Foundation-inspired specialty dining, 24-hour room service, a deck barbecue, champagne welcome, and complimentary access to the fitness centre, whirlpools, and sauna.
A lot of cruise lines release future seasons, but not every release signals a meaningful shift in variety and itinerary design. Windstar is framing winter 2027-2028 as one of its most diverse seasons yet, and the context supports that with both scale and specificity. It’s not only more dates, but it’s also the combination of new routes, limited-run sailings, and region-to-region range.
The season’s 230+ sailing dates matter because they make planning feel less like squeezing into one narrow window. Whether you’re coordinating school holidays, work leave, or long-haul flights, having a broader departure pool increases the chance you can pick the sailing you actually want, rather than settling for the only date available.
This is especially handy for international travellers. If you’re flying in from Australia, New Zealand, Asia, Europe, or North America, even a small shift in departure week can make a big difference to flight prices and the overall comfort of the travel plan.
Windstar is introducing 21 new itineraries departing between September 2027 and April 2028, and that’s a meaningful refresh for anyone who has sailed Windstar before and wants something that feels genuinely new. Even if you’re new to the brand, new itineraries often come with more thoughtful pacing and a clearer sense of what Windstar wants guests to experience in each region.
It also gives travellers more ways to match the trip to their travel mood. You can choose based on region, but also based on how immersive you want the itinerary to feel.
The context notes that many of the season’s cruises will operate during this winter programme only. That’s a big draw for travellers who prefer routes that feel a little rarer, rather than itineraries that run year after year unchanged.
It also makes the planning decision simpler. If one of these limited-run sailings aligns with a bucket-list destination, it’s worth considering earlier rather than later, because the opportunity may not repeat in the same way.
Windstar’s fleet deployment tells you a lot about what the line is prioritising. It also helps travellers understand what kind of onboard vibe they’ll have in each region, because different ships suit different itineraries and guest expectations. The winter 2027-2028 plan spreads ships across several high-interest regions without losing the small-ship focus.
Star Pride is set to sail in Latin America, Canada, New England, and the Caribbean. That’s a wide scope for a single season, and it suggests a mix of climates, port styles, and cultural experiences, depending on which part of the September-to-April window you choose.
For travellers, the upside is variety without changing cruise line style. You can choose a region that suits your preferred weather and shore interests, while still getting Windstar’s small-ship pacing and onboard inclusions.
The Caribbean is also hosting Star Legend and Wind Surf, reinforcing that Windstar sees strong demand for small-ship cruising in the region. Yacht-style Caribbean cruising tends to appeal to travellers who want a calmer onboard environment and ports that feel more personal.
If you’ve cruised the Caribbean on larger ships, the difference can feel immediate. You’re often trading mega-ship bustle for a more relaxed shipboard rhythm, which can make sea days and evenings feel more like a holiday and less like a schedule.
Wind Spirit will visit the Canary Islands, while Star Seeker is slated to cruise in Asia. Both regions suit small ships because itinerary design can prioritise access and variety without needing to cater to huge passenger volumes.
Asia is called out specifically for immersion, which suggests itineraries that lean into cultural discovery rather than just surface-level port sampling. The Canary Islands, on the other hand, are perfect for travellers who like island-to-island variety with a mix of relaxed days and scenic coastal time.
Windstar is reinforcing that the onboard experience isn’t separate from the destination experience. The food program, the onboard rituals, and the cultural event options are all positioned as part of what makes the season feel richer. That can be a deciding factor for travellers who care as much about the onboard rhythm as they do about the port list.
Every Windstar voyage includes complimentary specialty dining with menus inspired by local cuisine, created in collaboration with the James Beard Foundation. That’s a detail that speaks directly to travellers who see dining as part of how they experience a destination, not just a necessity between shore excursions.
It also gives the season a consistent “Windstar feel” no matter where you’re sailing. Whether you’re in Asia or the Caribbean, the dining approach is designed to connect you back to the region.
Windstar is also including 24-hour complimentary room service, an open-air deck barbecue, and a champagne welcome. Those things matter because they affect the everyday pace of the trip, not just the big moments.
Small rituals often become the most remembered parts of a cruise. A quiet breakfast in your stateroom after a late night, a barbecue with sea air and music, or that first welcome toast that tells you, “Yep, holiday has started.”
Select sailings feature one-night cultural Destination Discovery Events, which can be a standout for travellers who want something beyond a standard shore day. A single evening event can create a stronger emotional connection to a place, especially when it’s designed around local culture rather than generic entertainment.
This is also a smart fit for small ships. A boutique ship can often deliver a more intimate cultural evening, where guests feel like participants rather than spectators.
With so much regional variety, the best way to choose is to anchor your decision around the experience you want, not just the map. Windstar is clearly offering different “holiday moods” within the same season, and that can be a real advantage when you’re planning well ahead.
Tahiti is mentioned alongside the idea of a rare one-time-only South Pacific crossing, which is the kind of phrase that catches the attention of travellers who love meaningful routing. Crossings can be special because they create a sense of journey, not just a string of ports.
If you’re someone who enjoys sea days and the feeling of moving through a vast region, this is the kind of itinerary that can feel genuinely memorable, especially on a ship that’s designed to feel relaxed rather than crowded.
Windstar highlights immersive Asia itineraries, and Asia is a region where pacing and access can make or break the experience. A small-ship approach can help the trip feel more grounded, with a calmer onboard base that supports full days ashore.
This is also a strong choice for travellers who like meaningful cultural experiences but still want comfort and simplicity built into the travel plan.
The Caribbean and Canary Islands are positioned for yacht-style cruising, which usually means an easygoing onboard feel and a strong emphasis on access and freedom. If you want the kind of holiday where your days can be as active or as relaxed as you like, these regions fit naturally.
It’s also where Windstar’s open-air deck barbecue and wellness access can become part of the trip’s rhythm, because the climate and scenery encourage more time outside.
If you’re looking at Windstar’s winter 2027-2028 options and want to compare regions, dates, and ship deployments side-by-side, the easiest starting point is the Cruise Finder. It’s a quick way to narrow the season down to the sailings that match your travel window first, then you can go deeper on itinerary style.
Once you’ve got a shortlist, the Cruise Finder also helps you sanity-check how each route fits with flights and pre- or post-cruise plans, especially if you’re travelling internationally and want the whole trip to feel smooth.
Windstar’s winter 2027-2028 programme is built for travellers who want more than just sunshine; it’s designed for access, variety, and a small-ship approach that supports deeper discovery. If you’re ready to lock in a sailing while the new itineraries and limited-run routes are available, the next step is matching the right region and ship to your travel style.
When you’re ready, you can reach out to S.W. Black Travel to plan your Windstar winter cruise, and we’ll help you compare the new itineraries, identify the limited-run sailings worth prioritising, and choose the best stateroom setup for the way you like to travel, whether you’re departing from Australia or joining from anywhere else around the world.