The Birth of All-Season Travel

Across Europe, Africa and the Caribbean. the concept of “low season” continues to shift. Mark Ellwood looks at what it means for travelers. Plus: Our favorite places for all-season trips.

Call them the double-dippers.

Lake Como–based hotelier Valentina de Santis has seen a surprising shift in travel at her new property, Passalacqua, the year-old sibling to her family’s long-standing landmark, Grand Hotel Tremezzo. Valentina opened the second hotel expressly to operate differently from the seasonal rhythms that have dominated the area. “That was the initial idea, to make it an almost year-round property,” she recalls, noting that it was more than just a chance to increase profits. Extended contracts would allow her to hire better, more local staff, for example. “And it’s about being able to distribute guests over a wider period, because of overcrowding. It’s a win-win.”

The Caribbean has traditionally been a region with drastic differences between its peaks and lows. “But there is no offseason anymore,” shrugs Fabrice Moizan, the longtime GM of the Eden Rock in St Barth’s. He has seen the same shift as de Santis reports as well as the emergence of a new class of double-dippers. Occupancy is up: rates in his low season—the summer—typically hovered around 65 to 70 percent pre-pandemic, while this summer, it was 90 percent. “Most of the additional occupancy is from existing clients who came during the winter but had never experienced it during the summer,” he adds, with summertime trips often shorter, perhaps an impromptu long weekend. It’s much easier to be spontaneous then, of course: yachts are easier to charter for the day, and restaurant reservations less fraught than over the festive period. “The vibe, the ambience, though, it’s still very entertaining.”

The Grand Hotel Minerva in Florence has seen the same pattern in its guests, per owner Sara Maestrelli, citing one regular who came for several weeks in July this year with her extended family; by September, she returned with her husband for a romantic getaway, a last-minute, double-dipping booking. Maestrelli is prepping to open another hotel in her collection later this year, the Violino d’Oro in Venice, which will be expressly marketed as an offseason choice. Its website will feature a dedicated section for low-season travel, dubbed Underwater Love; she notes that the issues around flooding in winter—acqua alta, as the locals call it—which often deterred luxury visitors, have been largely resolved since the installation of the MOSE dam in 2020. “Venice is at its most authentic in November or January, the exact same atmosphere that’s described in so many novels,” Maestrelli adds.

“Venice is at its most authentic in November or January, the exact same atmosphere that’s described in so many novels.”

It's seasoned safari-goers who are helping to fill rooms in what was previously low or green season at Matetsi in Zimbabwe, too, at least per Sara Gardiner who owns the resort. More agents have asked her about the green season, so they can better discuss the idea with their clients. “These are people looking for an atypical safari experience,” she says of her double-dippers. “They might want to see the tiny baby animals that appear with the first rains. And in our area, we see more leopard activity in the green season—they walk in the roads to keep out of the wet grass.” In the Greek Islands, there’s been a similar change, at least when resorts are able to operate beyond their traditional parameters. Daniel Kerzner’s plans for his Santorini Sky resort, which opened in summer 2020, included the aim of operating year-round, except for a brief break between Christmas and New Year’s. The villas are winterized, and private pools are heated; he even invested in Starlink Internet, to offset the fact that bandwidth is throttled to the islands in November or so once the tourists depart. “Sitting in a 95-degree Jacuzzi in the snow on a mountain in Santorini in the winter? That experience is as incredible as any sunset in Oia,” Kerzner says.

Why, then, has the new trend emerged? Overtourism, of course, is one reason for changing travel patterns, an issue that’s particularly acute in locations like where Kerzner operates: guests might come in the summer to hole up and decompress, then decide to return off-season to explore at leisure without risk of crowds and congestion. Much of the island might be shuttered, of course, but there’s also a keener sense of real life, a chance to spend time with locals rather than fellow tourists. Valentina de Santis echoes that idea: almost half her guests in summer are American, but that drops to around one-third off-season, with many more Italians—an added appeal in itself. Both Santorini Sky and Passalacqua, of course, hire staffers for a full year, which means even the workers are more likely to have local know-how.

Even the wealthiest are noticing the uptick in rates in the pandemic’s wake— luxury hotels are more than 50 percent more expensive per night than they were at comparable dates four years ago. So, the fact that rates at five-star properties are 30 to 40 percent cheaper than at peak is an added incentive for a bonus trip. Crucially, though, shoulder or low season rates at high-end properties remain pricey enough to retain an appeal to the same clientele. “It’s not people who have never been to a five-star hotel, splurging, ” says de Santis. “That’s key for a hotel: to have the same kind of clients all the time.”

Daniel Kerzner says the pandemic-induced sense of carpe diem around travel persists, too—a focus on the why not? rather than the why? “A reason to come trumps the calendar or seasonality now—if you have a special birthday in February, and have always wanted to go to Santorini, you’ll book then. If I look at my bookings for next February, it’s weddings, anniversaries, birthdays, so many different reasons for people traveling.” Anyone nervous about risking a trip outside the seasons when conditions are supposed to be more reliable can even opt for new insurance offered by the four-year-old Californian start-up Sensible Weather: sign up for one of its policies and there’s an automatic payout if your vacation’s wrecked by bad weather.

Wintry storms in Lake Como won’t matter to the guests at Passalacqua this year. Following the success of its first extended season last year, de Santis is shuttering earlier in 2023, but for good reason. She’s decided to shutter a little earlier to add a long-planned amenity to the property that’s aimed at helping her remain open for all but six weeks or so every year: an indoor pool. It’s the perfect place for that double dip.

Written by Mark Ellwood

5 (More) To Know: All Season Favorites

Schloss Elmau, Germany

Why We Love it for All Seasons: Complete with a long list of outdoor activities, from hiking to snowshoeing, this varied and interesting location has something for all activities levels and all seasons. Elmau is known for its incredible wellness facilities, with six separate spas and pools for adults and families, an ideal solution for those rare rainy days where you just want to stay put.

Who Should Stay: Families, spa goers and active types

Awasi Patagonia, Chile

Set on a private reserve on the edge Torres del Paine National Park, this Nordic-style lodge is made up of 14 bungalows-on-stilts, each of which comes with a private guide and a 4x4 vehicle for customized excursions.

Why We Love it for All Seasons: Excursions in Patagonia—be it horseback riding or trekking amidst dramatic scenery—are always weather dependent, but every season showcases a fresh side of the destination: fiery fall colors March to May; ice and snow frosted glaciers June to August; wildflowers and wildlife September to November; and long warm days ideal for hiking and water activities December to February.

Who Should Stay: Couples and families with children over 10

The Brando, Tahiti

This eco-luxury private island resort sits on an atoll in French Polynesia and has 36 accommodations including villas and a residence, all surrounded by abundant flora and fauna.

Why We Love it for All Seasons: A trip to the Brando is both an escape from the real world and an escape from the seasons. Here, guests reap the benefits of the vibrant nature and sustainability programming year-round, be it snorkeling in the coral garden, visiting a bird sanctuary or shark nursery, diving into Polynesian culture or languishing at the spa (all of which are only a taste of the offerings).

Who Should Stay: Couples, families and groups of friends

Ranch at Rock Creek, Montana

Surrounded by 6,600 acres of flowering hills, snow-peaked mountains and pine forests, Ranch at Rock Creek is a Wild West fantasy made real, complete with a saloon and 70-horse herd.

Why We Love it for All Seasons: While warmer months mean archery, horse-back riding, hiking and fly-fishing at one of the United States’s best trout runs, the winter season here ushers in days of horse-drawn sleigh rides, snowmobiling and skiing. And for those days where the weather doesn’t cooperate, there’s an indoor bowling alley and movie theater.

Who Should Stay: Anyone who loves the American West and outdoor adventure

La Mamounia, Marrakech