Live Like a Local Foreigner: Long-term Escapes and Private Homes

Courtesy Mustique Company

Courtesy Mustique Company

Come on in & Stay a while

We’ve all played the game - sharing a bottle of wine with friends and asking, “If you could live anywhere else, where would you go?” These days, happy hours may be more virtual than physical, but the fantasy of packing up and testing out a new home base is more viable (and tempting) than ever.

It would be disingenuous to say there’s a lot we’ve loved about life in lockdown, especially now that the novelty is very much gone - sourdough starters have been pushed to the back of the fridge, forgotten, and noble goals of watching all the Oscar winners for Best Picture in chronological order were abandoned somewhere in the early ‘40s - but everyone working and learning from home has brought about a sort of slow flexibility. Sure, we can’t quite go jetting off for the action-packed vacations in far-flung locales that we love planning for clients (and experiencing ourselves), but as the season begins to change, we are seeing more friends and travelers decide to take the plunge on that happy hour-hypothetical and try out a new temporary home base.

Now is the time to trade the city for the country, the east for the west, Central Park for the great outdoors - think of it as the chance to take a grown-up semester abroad, without the youth hostels and EurRail pass. You know we are hotel experts, and we apply that same level of discernment to our portfolio of private homes and villas. Below, we’ve highlighted a few destinations that would make for a dreamy long-term escape this fall, but we have access to incredible homes all across the country and beyond, so there’s lots more where these came from. We put the TLF touch on every home, and are here to help with all the details - grocery stocking, private chefs, housekeeping, personal trainers, concierge services - you name it. We make travel better, but we also know there's no place like home.


The Hamptons

The Hamptons are the obvious long-weekend destination of choice for New Yorkers between Memorial Day and Labor Day, but they’re just as magical in the fall. During the summer, it’s easy to be distracted by the beach scene, but once temperatures start to taper, it’s time to take advantage of the incredible art on offer along the South Fork - stroll the grounds of Longhouse Reserve, a 16-acre sculpture garden with works by Buckminster Fuller, Yoko Ono, and Willem de Kooning; on moodier days, duck into the Parrish Art Museum to check out the 3,000-plus works ranging from early nineteenth-century landscapes to contemporary pieces.

The farm stand game is particularly strong out east - as the summer tomatoes and sweet corn disappear, they’re replaced by brussels sprouts, romanesco, and pumpkins. We love Balsam Farms in Amagansett and Serene Green in Sag Harbor; pick up some aged cheddar from Cavaniola’s Gourmet and a sauv blanc from the Wölffer Wine Stand, and you may find yourself wondering how you’ll ever go back to Seamless and Fresh Direct.

Picture coming home to…

A gated private estate home surrounded by a hundred-acre reserve
Where: East Hampton, New York
The Specs: 5 bedrooms | 5,200 sq ft | Up to 12 guests
The Fun Stuff: Chef’s kitchen, pool, spa, fireplaces, bonus room, outdoor living room
Priced From: Price upon request; available weekly or monthly


Jackson Hole

Fall in Jackson means a front-row seat for blazing autumn landscapes. Clutches of aspens start to yellow in late September, before deepening to gold and finally flaming out in a riot of reds and oranges. Swaths of flaxen cottonwoods add to the dramatic performance. Plus, the crowds that swarm into the national parks in the summer have mostly dispersed, meaning instead of spending your Saturday morning dodging Citibikes on your way to La Colombe, you’ll be donning flannel and hiking boots, grabbing a cortado to go at Persephone, and heading out into Yellowstone or Grand Teton to explore the parks in peace. You may even catch the eerie sounds of male elk bugling, as it’s rut season before the herds migrate out of the high country ahead of the cold - beats waking up to the sound of a honking cab any day.

Picture coming home to…

A creek-side chalet with incredible views of Jackson Hole’s Cirque black diamond ski run
Where: Teton Village, Wyoming
The Specs: 6 bedrooms | 7,079 sq ft | Up to 15 guests
The Fun Stuff: Screening room, bar, hot tub, game room with pool table
Priced From: From $35,000++ per week; available weekly or monthly

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Lake Tahoe

Those looking for a quick pick-me-up can still take a dive into the lake through September, as it’s spent the summer heating up (though at depths of up to 1,645 feet, even at its warmest, a dip is a bit bracing.) Come October, kokanee salmon start their annual upstream swim to spawn, meaning it’s prime time for spotting black bears fattening up before the snow comes.

And come it will, whether natural or man-made - by Thanksgiving, the area’s world-class ski resorts will start to open, offering the some of the best ski and snowboard terrain anywhere. But if you’re seeking a different type of inspiration, there’s a healthy literary streak that runs through the Sierra Nevadas, inspiring writers like Mark Twain (who said of the area, “it must surely be the fairest picture the whole earth affords”) and naturalist and author John Muir, who wrote, “This is true freedom, a good practical sort of immortality." So if you’ve been dreaming of writing your first novel or tapping into your inner poet, Tahoe may be just the inspiration you’ve been seeking.

Picture coming home to…

A sprawling lawn with views over the lake makes for a year-round family playground
Where: West Shore, Lake Tahoe
The Specs: 7 bedrooms | 7,500 sq ft | Up to 16 guests
The Fun Stuff: Home theater, outdoor grill, fire pit, hot tub, dock, guest house, and teepee
Priced From: Price upon request; available weekly or monthly

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St Barth’s

While the Caribbean is just starting to close its doors for hurricane season, it will be October before we know it, and the white sand beaches will be open once again. Base yourself in the hills above Gustavia, so you can watch the sun set into the water over those iconic red rooftops. With average temperatures hovering right around 80 through November and December, you can live out your endless summer fantasies as friends in the states despair over ever-encroaching winter nights. Rent a mini moke for the season and the island is your oyster, giving you the flexibility and time to explore off-the-beaten path beaches and private coves.

While St Barth’s is often thought of as a spot for grown-ups to cut loose, kids will love spending an extended period of time on the island, running around barefoot and playing marine biologist - it’s a perfect opportunity for those 10 and up to get PADI certified and learn about the underwater life, which is just as fabulous and colorful as anything happening at Nikki Beach.

Picture coming home to…

This stylish new build with views of Flamands Beach, with spots to gather and to hide
Where: Colombier, St Barth's
The Specs: 5 bedrooms | 5 baths | Up to 12 guests
The Fun Stuff: Infinity pool, fitness center, massage room, turn down service, media room, charcoal and gas grills
Priced From: From $36,000++ per week



There are few places more discreet than Mustique, an all-villa private island in the Grenadines, frequented by those who want to fly under the radar. Hole up in one of the hundred or so historic and fantastical private homes, which come fully staffed and equipped for the island-life fantasy, like a luxury version of William Pène du Bois’ 21 Balloons (but without the world-shaking volcanic action.) Instead of Phys Ed, the kids can head to morning tennis lessons or horseback ride along the sand; Saturday afternoon means beach barbecue (and you don’t have to do the dishes.) Though it’s the most overused phrase of 2020, we’re okay talking about the “new normal” if that new normal is life on Mustique.

Picture coming home to…

A serene paradise named for the Brazilian goddess of the sea on seven island acres
Where: Mustique, St Vincent & The Grenadines
The Specs: 8 bedrooms | 19,000 sq ft | Up to 16 guests
The Fun Stuff: Full staff, 3 pools, pool pavilion, tennis court, 4 x 5-seater Kawasaki mules
Priced From: From $35,000++ per week