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Business News/ Special Report / The Secret to a Better Vacation? Don’t Go at the ‘Best’ Time

The Secret to a Better Vacation? Don’t Go at the ‘Best’ Time


If you travel during the off season, you can beat the crowds, save money and actually have a more fulfilling experience. Our writer ventures to a winter beach town—and finds many rewards.

The Secret to a Better Vacation? Don’t Go at the ‘Best’ TimePremium
The Secret to a Better Vacation? Don’t Go at the ‘Best’ Time

“THIS IS way harder to do in the summer," Evan Bucholz said as he raised his glass and then knocked back a 50-50 shot of amaro and something stronger. I followed suit. Bucholz, mixologist and co-owner of the bar Brix & Rye in the town of Greenport, N.Y., was talking about the trickiness of finding time to indulge in a drink with a customer, and the spirited discussion we’d just had. He always tries to connect with guests, he told me, but on some nights in the summer it’s just impossible. “As soon as that door opens, the place gets slammed—it can be difficult to stop and chat."

Greenport, once a whaling hub, sits on the North Fork of Long Island, the sliver of land that extends east from Manhattan until it splits like a fishtail into the Atlantic. Come summer, this area’s population swells with vacationing families, as in so many beachy locales within driving distance of New York City—the Jersey Shore, the Hamptons. When fall settles in on the North Fork, the beachcombers head home to nurse their sunburns and the pumpkin-crazed hayriders arrive. “Winter is when I really get to experience the things I miss out on in the summer months," Bucholz said.

I had come here in January to see what it looks like when the crowds disperse. Would I spend 48 hours wandering aimlessly between shuttered businesses in the cold winter rain? Or could my visit confirm my own burgeoning hypothesis: that if we, as tourists, manage to resist the pull of the high season and stop thinking in terms of the “wrong" and “right" time to visit a place, we could unlock travel experiences that are more rewarding? And more sustainable, too, when overtourism is growing as a threat?

Over the course of two days, I survived without the hallmark moments of a picture-perfect North Fork weekend: No rapidly melting ice cream dripped down the side of my hand; no sun-drenched naps were had on the sand. Instead, I bundled up and walked the empty beaches of Orient Point, the very tip of the North Fork, watching as robins in their hundreds swarmed the nearby treetops and the sea frothed. At Nookies, the new diner at the nostalgia-heavy Silver Sands Motel, I enjoyed a meal unpressured by others waiting their turn. And the North Fork’s vineyards, among the area’s main draws, were all the more inviting, wrapped in dense winter fog, soft light flickering through the windows.

It brought to mind other trips I’ve taken, when arriving at the “wrong time to go" actually opened doors. On a visit to Senegal in September, during the rainy season, I was met with humidity so dense walking felt like swimming; but it also led to easy friendships. As one of the few tourists, I could enjoy more meaningful, less transactional interactions with locals.

Even pushing a trip back several weeks past the tourism peak has reaped rewards. Visiting Provence last October meant cold nights and the occasional rain shower. But the London plane trees glowed in autumnal yellow and the freedom to visit restaurants without booking meals months in advance allowed for spontaneity. As I rode a bicycle down an empty country road, it seemed impossible I’d ever encounter traffic.

On the North Fork too, I got so used to having breathing room that any semblance of a crowd shocked me. The tasting room at Macari Vineyards was mostly full when I showed up on a drizzly Saturday afternoon. Gabriella Macari, whose grandfather started the vineyard in 1995, says that in recent years she’s started to see the line between high and low seasons blur. At least within the cozy confines of this winery, the secret of the off season, it seemed, was out.

But even a marginally slower winter, Macari says, means a less-rushed relationship with visitors. “I think people who have maybe come once in the summer make the decision to come back when not everyone’s going," she said. In the summer, she added, she and her staff must focus on “reacting" to the constant stream of customers. “In the winter we can take our time to connect with people—and I think visitors seek that out."

For most, the appeal of the off season starts not with an intangible desire for connection but with savings. The Menhaden hotel in the heart of Greenport cost me about $270 a night before taxes and fees. On Memorial Day weekend, the same room goes for around $800 a night.

“Sometimes I’ll quote someone a few hotels in southern Europe in July and the prices will be very high," said Paul Tumpowsky, founder of New Yonder, a luxury travel advisory focused on young affluent travelers. “And they might review these prices and think: ‘Oh, when else could I go?’ That question opens up whole new possibilities."

Clients unconcerned with prices, Tumpowsky says, are still enticed to travel in quieter months by the promise of sparse crowds. “The only time ultrawealthy travelers tolerate crowds is either when they’re in front of them or when it’s a particularly big event where they’re gaining access," Tumpowsky said.

Setting expectations and being realistic are key, says Pamela Garza, founder of Tory Ellers, a membership-based travel advisory. Though she’s not sending customers to Italy’s Amalfi Coast deep into winter when businesses shut down, she still nudges them to break away from convention. “I’ll tell people to outright avoid July and August on the Amalfi Coast, even if it means you have to deal with a few cloudy days," Garza said.

Similarly, Garza increasingly recommends safari-goers book trips between December and March—the “green season," when the rains in Botswana transform the area around the Okavango Delta into lush grassland. Conventional wisdom says the dry season is best for spotting game, as animals (and Land Cruisers) thirstily congregate around water sources. But Garza says travelers can have a different kind of wildlife experience—and save up to 30%—if they go later. “One of the coolest things about going to Botswana in the off season is that you get to actually see the guides use their tracking skills," Garza said. “It’s a thrilling thing to search for and find these animals without other people around."

The more travelers I spoke to, the more I realized everyone has that place they love in the off season—the secret they can’t wait to spill. Lucy Pabst, 26, a ranger with the National Park Service, always recommends people visit the Grand Canyon in winter, though she cautions them that some services won’t be available. “You can hike and travel into the canyon much farther than in the summer since heat stroke isn’t a risk," Pabst said. In the warm months, by contrast, medical evacuations are a “nearly daily" occurrence.

While saving money and avoiding the crush of crowds might help drive people to break from the herd, both those instincts point to a greater, more elusive desire: access to an experience we can call genuine. The thrill of the chase as you follow a leopard’s tracks across the plains; the promise of adventure deep in the Grand Canyon; a meandering conversation in a warm bar on a cold night.

Like me, Julia Easterlin, a 35-year-old musician based in Brooklyn, loves a cold beach. For her, it started with an impromptu trip during her college years. In the waning days of winter, she put “Cape Cod" into her GPS and hit the road. “It was quiet and freezing and dark, and everyone seemed startled to see me," she recalled. But she loved having the time to think, talk to locals and go for long walks. She’s been back a few times since, chasing in the off season what she can’t find around fairweather tourists. “There’s space to notice where you are," she said.

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