At the end of one year and the beginning of the next there’s always a lot of coverage in the media about travel trends. And of course they’re often focused on destinations. In one list of “hot” destinations, Forbes Travel Guide tells us that big events like the Formula 1 race in Monaco makes its list of top destinations (we’re ahead of Forbes on that one, see why). Greece’s Athens Riviera, just ten miles south of Athens (and a perfect pre- or post-Greek Isles stay) makes the cut. Amsterdam celebrates 750th anniversary in 2025.
A lot of the “new” trends for 2025 that I’ve come across over the past few weeks aren’t all that new. Booking.com tells us that the baby boomer generation (people born from 1946 – 1964) is more interested in “high-octane adventures” for the more adventurous among us but our itineraries, particularly in the Caribbean, Tahiti and Central America/Panama Canal have long featured active-focused shore excursion menus.
We do love Expedia’s “phenomena list” which, again, isn’t a new concept, but highlights some really cool lures of certain destinations, like Iceland’s lava fields and black sand beaches; we’d add that our August 2026 “solar eclipse” voyage (pictured above) around Iceland is going to be special.
More than just focusing on trendy, in-demand places to visit in 2025, however, we’re seeing that travelers are intrigued by experiences and trips that allow explorations in new ways, not just in 2025 but also for several years to come. We turned to Jess Peterson, Windstar’s director of destination experience & itinerary planning, who stays up on shifts and changes as he and his team are now planning itineraries and laying the groundwork as far ahead as 2028 (only our voyages through June 2026 have been announced, so watch this space!).
“Whether it’s visiting a new place or reconnecting with a much-loved destination, one trend we’re seeing amidst our own travelers is the desire to experience travel with fresh eyes,” he tells me. Specifically, here’s how Windstar is evolving its own voyages through 2027.
Second cities
Last year, there were a lot of travel headlines that focused on over-tourism, especially (but not limited to) in Europe, where demonstrations (and hiked fees for visitors) occurred in places such as Barcelona, Santorini, Amsterdam, Dubrovnik, Venice and more. Peterson says that as his team develops new itineraries, it is looking increasingly at “second cities.”
While Windstar still does sail in and out of major destinations, lesser-known places in relatively close proximity offer travelers a new twist. “Milos, in northern Greece, is a great example,” he says. “It’s much less crowded, very beautiful and our guests who have visited really like it. Reggio Calabria, the toe of Italy’s boot, is quite new to Windstar, and gets very few cruise calls. In Asia, we have a strong Japan program that visits many “second cities” there in addition to Tokyo and Kyoto. We’ll also be expanding to Vietnam and Thailand.”
It’s not just where you go, it’s when
My best trip in the last few years was a then-new offering from Windstar – a late winter sailing from Rome’s Civitavecchia to Barcelona, via Florence, Nice, and Marseilles. I’d been to all of these cities before during more popular travel months in spring, summer and fall. Winter was special; temperatures were reasonably comfortable, crowds were sparse, and because it wasn’t high tourist season, I felt like I was having more of a local experience. I joined residents in visiting art museums and galleries, and indulging in long, lazy lunches at locals’ trattorias, bistros and markets. In fact I loved the experience so much I signed up to cruise from Venice to Rome (via Croatia and Sicily) in January of 2025. I can’t wait to see these much loved destinations through fresh seasonal eyes.
Windstar’s year-round schedule of Mediterranean sailings has expanded in 2025 to include the Iberian peninsula and the Adriatic; the opportunity to explore coastal Christmas markets during the festive season is another lure.
Longer trips, more flexibility
As many travelers today are choosing more flexible work schedules, cutting back on career-long responsibilities or retiring altogether, taking longer trips, consisting of disparate parts, is more popular.
“One trend we’re seeing among our guests is a twist on back-to-back cruising,” Mathy Wasserman, a partner in Flying Giraffe Travel, tells me. Cruise lines are still creating “back-to-backs” that can be booked as seven, 14 or 21 days without visiting the same port twice. What’s new, she tells me, is that clients (and their vacation planners) are cobbling together a selection of experiences that all connect. Some are starting off their European vacations with a cruise, then flying to a nearby destination for a villa rental experience, and then hopping back onboard.
You don’t have to plan everything separately, either. Windstar recently launched a new tour option that combines a Tahitian cruise with a stay at the magnificent Brando Resort.
New approaches in popular cruise regions
Maybe you’ve traveled to Rome, Naples, and Venice a number of times. But have you ever experienced Italians’ vacations at the beach in summer? Peterson says that Windstar has created a new itinerary, roundtrip from Rome, that offers a beach-oriented adventure, visiting places such as Corsica and Sardinia and expanding the opportunities for the ships’ marinas to be open.
French Polynesia is another in which Windstar is creating new experiences, adding trips to the exotic Marquesas and another to Fiji and the Cook Islands that can be itineraries in their own rights – and also be combined with Society Island sailings.
And if you think you’ve been there and done that on a Canada/New England cruise, a new opportunity opens up in autumn of 2026 with an intensive 14-night Newfoundland cruise, operating from Montreal.
Where are you hankering to travel or, better yet, what types of trips are you considering
For his part, Peterson, who just returned from an itinerary planning trip to Vietnam, can’t wait until that itinerary will be finalized for 2027. “It’s brand new,” he says, “and I can’t wait to experience it – this time as a passenger.”
What about you? Where will you go this year and next? Will you travel differently (multi-generational, honeymoon, or a phenomena sailing ) — or all three? Please share your plans in the comments below.
