We love this time of year—the time of year when we try on last year’s ski pants and start digging around for the best winter weekend trips. Of course, the mountains are calling, but then again, the beaches are calling, too. We wanted to focus on the places that put a premium on making you feel relaxed, warm, cared for—whether that means a walk along a wide, empty beach or the peace that comes from a flawless ski run. It took us a minute to realize that off-season is the best season at the beach. And ski weekends don’t exist any other time of year.
Of course, there is the matter of getting there. High travel season is also high stress season. And high flight cancellation season. And high “let’s stay home” season. That’s why there are two words that seem especially luxurious this time of year: “flying private.” And by “flying private,” we mean NetJets—the largest private fleet of aircraft in the world. To be specific, we’re talking about more than 750 planes, nearly 6,500 aviation experts, and access to more than 3,000 airports in 180-plus countries. NetJets has essentially turned the entire country into your own backyard. It goes like this: If you’re a NetJets owner (membership is tiered so you can own a share, a lease, or a card), you effectively own your own plane, so you can fly to Sun Valley or Nantucket or wherever you want whenever you feel like it. Sorry, did we say “or”? We meant “and.”
Nothing can prepare you for the rugged beauty of the Tetons. It’s shocking enough to make you pull over, turn the engine off, and just stare at the majesty of it all. In Jackson Hole, the hotels, restaurants, amenities, and views live up to the hype. And we’re talking about a lot of hype. Amangani is the überluxurious option, but for something boutique and more convenient to the ski lifts, it’s hard to beat Caldera House. (Take note: Both Caldera House and the Four Seasons have partnerships with NetJets, ensuring that you get the same impeccable service on the ground that you get at 41,000 feet.) Caldera has just eight suites, each with two or four bedrooms and a fully equipped kitchen, making it the ideal situation if you’re traveling with friends or kids or friends with kids. Décorwise, let’s just say if we could move into the mountain-chic Scandinavia-meets-Wild-West space tomorrow, we’d never look back. After a day zipping around the slopes, head over to the Four Seasons’ Handle Bar for an après-ski whiskey. And before one becomes two, make your way to Glorietta for the town’s best brown-butter ricotta cavatelli. For a dose of midwestern Americana—live country music, vintage license plates, taxidermy (we’ve warned you)—fight through the crowds to the second floor of the Mangy Moose. Oh, and if your cheeks are windburned and chapped the next morning, make a beeline for Alpyn Beauty Bar—it has a great selection of creams and balms wild-crafted from alpine botanicals.
Sun Valley, on the southern side of Idaho’s Sawtooth National Forest, is a laid-back, intensely local, North Face puffers and beanie hats kind of ski town. In fact, it’s so local that there are hardly any hotels—although there are luxury “cabins” available to rent, and the Sun Valley Lodge is incredibly comfortable. Try to book a suite with a fireplace and terraces overlooking both Bald Mountain and Dollar Mountain—it’s a hell of a way to wake up. Thanks to a network of snowmaking guns, fresh powder is never a problem during ski season. And in the summer, the wildflower-lined trails, lakes, and creeks offer hiking and fly-fishing to rival the Dolomites. When it’s time to eat, head to Ketchum—the meatloaf at the organic deli Nourishme is as famous as the “bowl of soul” (a delicately spiced mocha topped with a cloud of whipped cream) at Java on Fourth. The terrace at Cristina’s is made for hours-long, Tuscan-inspired lunches that start with a heaping platter of antipasti and end with a round of espressos. There are plenty of steak-and-potatoes establishments around town, and Southeast Asian Rickshaw makes the tastiest pickled cucumbers and spicy udon noodles anywhere in this time zone—plus we can never resist a spot with an outdoor firepit. Sun Valley is definitely not the seat of sartorial elegance, and we love that about it. But if you have a penchant for fly-fishing and fleeces, this is your jam. (Speaking of, Silver Creek Outfitters is a mecca of outdoorsy apparel, fly hooks, and stellar intel about the area from the staffers.)
As romantic as dashing away to Nantucket may sound, there’s no getting around the fact that it’s an island in the Atlantic—which explains why plans fizzle out around the time you say, “ferry schedule.” The NetJets route here is simpler, easier, and more direct—both geographically and emotionally. The minute you land in Nantucket, the early eighteenth century reveals itself with the Quakers’ signature modest, pitched roofs all over the island. The simple charm of those old wood dwellings and cobblestone streets is now fully ingrained in the island’s architectural DNA, which is reflected in the hotels here. Topping the list is Greydon House (designed by Roman and Williams, the masters of luxurious comfort). Imagine an old-world inn with twenty rooms and communal spaces so gorgeously appointed that leaving the premises feels like a missed opportunity. White shiplap walls are the perfect backdrop for patterned quilts and moody landscape paintings. Bathrooms are gorgeous and inviting with hand-painted Portuguese tiling in all the showers and the fluffiest of bathrobes. The restaurant, with its local bay scallops and grilled artichoke, has become a favorite among islanders. (The older but equally quaint White Elephant Inn is a second stellar option.) If you happen to be on Nantucket between May and November—the high season—visit the Whaling Museum: It chronicles the island’s long history alongside a forty-six-foot sperm whale skeleton. It’s as fascinating as it is informative, especially if you haven’t read Moby Dick since college. Year-round, Roastd General Store brews velvety lattes spiked with Moon Juice Dusts, local bee pollen, and chaga. Grab a brew to go before you head out for a walk on Sconset Bluff.
Winter is the most underrated time of year in the Hamptons. That’s when this place shakes off its summer fabulousness and settles back into its authentic, almost rustic roots. Brisk, wrapped-in-woolens walks on Cooper’s Beach and cozy suppers at OG spots, like Nick & Toni’s, become the norm. Unlike other beachy enclaves on the East Coast—and thanks to a loyal local population—the Hamptons never completely shutter. In fact, reservations that are impossible to get in the summer months are no problem in the fall. If it’s Friday night, head over to the Wölffer Estate Wine Stand for candlelit tastings and probably too much cheese. On Saturday, make your way to Loaves & Fishes in Sagaponack for a picnic lunch of sandwiches, potato salad, and pear galettes. It’s the perfect meal to bring on your hike out to the Montauk Lighthouse—just brace yourself to be a little whipped around by the wild Atlantic gusts. But where to sleep? Shou Sugi Ban House is a recent addition to Water Mill’s accommodation portfolio, and there’s nothing else like it on the East End. Designed with a Japanese sensibility, there are no cluttered corners in the thirteen-room wellness-themed hideaway. Guest studios come with hinoki-wood soaking tubs, fireplaces, and dedicated massage areas. Regular programming includes Reiki, Qigong, aerial yoga, meditation, and an array of Japanese water-based therapies at the spa. Before you leave the Hamptons, drop by Ulla Johnson for a new puffy-sleeve knit sweater or maybe a few velvet scrunchies—somehow they make the transition from Sunday by the sea to Monday in the city more bearable.