Where are you wintering?
It snuck up on you, didn't it.
Feel free to listen to an audio recording of this text while you’re packing for Aspen and looking for your missing ski glove that you will find when you get home with a new pair of $230 gloves:
Right around the time when holiday music and decorations become nightmarish is when the kind of people who summer begin panicking about where to winter. This wave of champagne stress begins on the Wednesday of the second week of January, when extended New Years travels have ended, the persistence of an OOO autoresponder email message becomes an employment liability even for VCs, and the first tax-related document (for advisory services that you don’t even remember providing) arrives in the mail. If you are reading this and you are not already wintering, you are in good company, because everyone with an Amex Platinum or a Chase Sapphire card is losing their minds about where to flee. This panic is justified, because winter planning is far more complex than summer planning for several reasons.
The many Winter holidays lull us into a false sense of complacent Winter joy.
The seasonal unearthing of our favorite cashmere sweater that we bought on the invitation-only first day of a sample sale is delightful and not a weather survival tactic, because we’re wearing it to a Friendsgiving party where we will immediately take it off, because the heat of oven, the density of bodies, and the volume of smalltalk has made it feel like South Carolina in August. Seeing our breath in the air for the first time is novel and not an existential threat because it’s the month between Thanksgiving and Christmas, when the only reason anyone goes outside is to get into Ubers that take us to parties; the Fall work semester has ended, and no one will do anything industrious until mid-January. The first snowfall is beautiful and not a nuisance, because the dusting of white is illuminated by holiday lights. Or, if you’re in LA or Miami, the holiday lights illuminate the dusting of white around your nostrils, which is also beautiful as long as you have good genes or a good plastic surgeon.
All of this innocent wonder distracts us from the crushing reality that Winter is coming, and by the time we realize that we are in it, hotel rooms in Aspen that don’t even have a complimentary Keurig espresso machine are $2,000 a night, and getting a table at Carbone in Miami requires a brick of cocaine wrapped in hundreds tied together with a Jacob the Jeweler gold chain.
Wintering involves a lot of harried shuffling about.
While summering is a marathon – a long, slow, languid stretch of time in no more than two places (Europe and an East Coast American beach town) – wintering is a frenzied series of sprints. Because people - even you - are made of molecules, and the behavior of molecules is impacted by temperature, people naturally move further apart in the summer and move closer together in the winter.
For example, in the Summer, it is acceptable to spread out all over Europe as long as you are in Europe in June and July, and you can gush about how tranquil the month of August was on literally any beach along the East Coast as long as it is not in Florida. Winter movement is far more prescriptive in that one must spend short amounts of time with all the same people in small a number of approved wintering destinations.
There are only 13 official wintering destinations.
Wintering bodies operate in pack behavior, moving as a blob between Aspen, Bali, a boat in the Caribbean, the BVI, CDMX, Jackson Hole, Los Angeles, Miami, “Montana,” Nosara, St Barth, Utah, and any Alp that is not in Germany. In order for it to count as wintering, you must attend a minimum of 5 out of 13 of these locations for a collective stretch of no fewer than seven weeks. You can certainly go to other places to avoid winter, such as Puerto Rico, Vail, Tahoe, Tulum, San Miguel de Allende, and Santa Barbara, but these places are gross, and you will not be seen by anyone relevant.
To help you determine which wintering circuit you should subscribe to, read the following archetypical winter whines, and decide which one you could have plausibly whined to a friend on the roof of Petite Ermitage, in front of the DJ booth at Nightmoves, squished into a banquet at The Nines, or perched uncomfortably on a Moroccan pouf in the Mandrake Hotel during an experimental orchestral deep house set.
“I want to dress in 3 layers of cashmere and a Montcler coat, but I do not want it to be cold outside.”
Working in NYC fashion, fashion PR, or not working has afforded you the ability to work or not-work remotely. Your best bet is to rent a place in Pacific Palisades, or perhaps Venice Beach if the movie Leaving Las Vegas gave you the feels. Despite the fact that it rarely dips below 50 in LA unless you are sitting in a cold plunge, people in LA have the same number of cashmere sweaters and Montcler coats as people in NYC and northern European cities. This is because people in LA eat only celery, functional mushrooms, and Ozempic, and their smaller body fat composition and larger ego require more layers of expensive clothing even in warmer temperatures. LA is thus the perfect place to spend all seven weeks of January. You should spend the two or three or whatever weeks that comprise February in the other destinations with climates that support designer winter layering and allow you to have a more colorful conversation about where you wintered when everyone returns to NYC in second week of April: Aspen, CDMX, Miami, and a boat in the Caribbean, because being out on the open ocean can be chilly enough for cashmere.
“I still want to wear a big flat-brimmed hat even though hats are over, I have an $800 haircut, and I have never worked as a ranch hand.”
Aspen is a great place for people who want to say that they are going to Aspen. Common activities in Aspen include talking about Aspen, telling people who respond to your place-dropping Aspen Instagram story to come to Aspen (even though you cannot host them, because you are being hosted by your friend who works for a family office with a property in Aspen, and the use of the Aspen property is 30% of their comp), and saying that you are going to ski tomorrow but not actually skiing because you cannot ski. Aspen is also a great place to wear hats, because word has not traveled to 54-year-old divorcees from Dallas that big beige wide-brimmed beaver hats adorned with twigs and turquoise are highly correlated with involuntary celibacy.
If you do not have a home in Aspen, the maximum time to spend in Aspen is a 4-day weekend. If you do have a home in Aspen, the maximum time to spend in Aspen is still a 4-day weekend, because staying any longer makes it look like you are Aspen-house-poor and cannot afford to travel to Bali, Jackson Hole, LA, “Montana,” St Barth, and Verbier, which are the other destinations on the winter circuit for people who still wear hats.
“I want to say that I went skiing, but I do not ski.”
A great way of going skiing but not actually skiing is having a friend – such as Eric Schmidt or anyone who comes from money that was made during or prior to WWII – who is a member of the Yellowstone Club. The Yellowstone Club (or YC) is a private ski resort where the kind of people who winter go when they say they are going to Montana, similar to how people who were educated at Harvard say they went to school in Boston.
While it is possible to ski at YC, skiing-people-who-do-not-ski at YC eschew skiing in favor of wearing Bogner ski attire to the spa or to a basement level bar with filament lighting, wide-plank unfinished wood floors, and preserved western ephemera called The Boot, which was designed to make people who are wealthy enough to influence the government feel like they are just regular people who drink local beer, listen to ski-rock (yacht rock with a bit more acoustic guitar), and laugh about their helmet-head, even though they did not wear a helmet, because they did not ski. Other destinations where one can go skiing without skiing include Jackson Hole, the Stein Erickson Lodge at Deer Valley in Utah, and St Moritz. Aspen is a part of this circuit as well, but those who do not ski are excluded from the Aspenest part of Aspen, which is Cloud 9.
Cloud 9 is a mountain lunch restaurant that is only accessible via fairly advanced downhill skiing terrain that serves as a sort of figurative velvet rope before the actual velvet rope. The venue itself is a mash-up of a pre-2008 Manhattan nightclub, a table at Bagatelle on St Barth on New Years Eve, and a movie about a 1980s Dartmouth fraternity party. Cloud 9 is the only reason anyone ever washes ski clothing, because more Veuve Clicquot is sprayed by patrons at patrons in five seconds than is collectively consumed at five upper middle class bar mitvahs in northern New Jersey.
“I want to go skiing and actually ski, because skiing is my personality type.”
There is no better place for people whose Myers Briggs type is IFLS (I fucking live to ski) than Jackson Hole. Jackson is legendary not only for the number of torn ACLs, dislocated shoulders, and fractured patellas it produces per capita but also for the caliber of wealth that is packed into such a shitty looking town. Walk into the Monday night Hootenanny at the Silver Dollar Bar, and you will see billionaires socializing with centi-millionaires being served by millionaires, and everyone gets along despite the socio-economic divide, because they are all dressed like Lloyd Pierce from Yellowstone.
Other wintering destinations for people who have huskies named Alta and Powder and cannot have a conversation without mentioning that they heliski in Alaska include the entire state of Utah, Chamonix, and Val-d'Isère. Aspen is also a part of this circuit, but the personalities of skiing fanatics who go to Aspen are also equally defined by the real estate private equity firm called Vertical Ventures, Chairlift Partners, or Freshtracks Capital that they recently founded with their college roommate, whose last name is on the wings of several museums and hospitals in Manhattan.
“I live in New York because I like $8 lattes and I’m afraid of dying alone, but I cannot tolerate temperatures below 68 degrees, and I enjoy attracting mosquitos in February with MDMA sweat and The Moon by Frederic Malle.”
For people who cannot tolerate Winter, gluten, or anything that isn’t extremely expensive, there is no better place to winter than a boat in the Caribbean. The benefits of this winter circuit include being flown private from Van Nuys on a G700 to Princess Juliana International Airport in St. Maarten, walking 30 feet to a Sikorsky S-92 helicopter that will fly you to the deck of a boat that’s a bit too big to be directly in Gustavia Harbor, and being shown by staff to the stateroom where your host awaits you in an open monogrammed bathrobe. If this sounds like a gender-specific wintering circuit, it is, unless you are a 32-year-old former D1 college lacrosse player who worked in defense sales in El Segundo before meeting Donna Karan in the backyard of Moby’s in East Hampton while visiting his cousin who had a quarter-share at a summer share house in Montauk that was much closer to the public golf course than the beach.
Other wintering locations on the Winter-averse wintering circuit include Bali, Lyford Cay in the Bahamas, Miami on a really lucky weather weekend, a villa on St Barth, Tortola in the BVI, and an infrared sauna in Aspen.
“I want to get a head start on summering in Europe, and I like being photographed in a high-neck winter white turtleneck in front of fondue and raclette that I will definitely not eat.”
Gstaad was removed from the European wintering circuit for many years because, after its lavish 1980s peak, it was lampooned in the 1990s by Gen X because they couldn’t even get a job in advertising. Thanks to a more flattering variety of lampooning by Gstaad Guy, Gstaad is back as a peak destination for the kind of people who summer in Capri, are taught about prenups in preschool, and are told by their grandfather who their friends will be. Other excellent photo backdrops for groups of wintering friends who are friends because their ancestors collaborated to amass the kind of generational wealth that cripples their descendants into hollow vessels for rosé, recreational drugs, and SSRIs include Cortina, Kitzbühel, Megève, and - for the less fortunate - Verbier.
Verbier has been overrun by overextended Brits and international expats who have colonized Lisbon, but Club du Chalet Blanc is a members-only blue blood oasis in a nouveau riche desert. If Cloud 9 at Aspen is a second year associate at Goldman Sachs who grew up in Connecticut and gets angry when he drinks because he has a small penis, Chalet Blanc is a happily divorced 73-year-old third-generation Norwegian oil heir who stopped doing cocaine in the late 90s but tells the bartender to play ABBA’s Super Trouper and buys everyone in the club a round of peach schnapps during lunch.
“I live in Brooklyn, but I still want to winter.”
Residents of Brooklyn (which includes East LA, East London, and the entire Pacific Northwest) find it more difficult to winter, because the non-fungible vibe abundance they manifest in Bushwick doesn’t pay for a 3-day lift ticket at Aspen, which costs more than their Sunday-best sabahs and rent combined. The only fresh powder on the Brooklyn People Wintering Circuit will be handed to them in a chilled snogo by a friend of friend at LooLoo in CDMX.
Cuidad de Mexico (aka CDMX, or DF) is a perfect wintering hub for anyone who probably won’t ever sell their functional adaptogen elixir company to Unilever or be able to talk their parents into unlocking the lump sum of their $4m trust fund that disperses monthly in paralyzingly modest amounts. Despite the fact that the cost of short-term rentals has increased by 6,500% in the past four years due to restless Williamsburg residents who during the summer of 2020 wanted outdoor peyote and indoor tacos, CDMX is still an affordable wintering hub for people who have a lot of tattoos and unresolved childhood trauma.
The other superspreader spots on the Brooklyn People Wintering Circuit are Bali, the Wynwood area of Miami, the rapidly un-gentrifying parts of Venice Beach, the Bodhi Tree Yoga Resort in Nosara, and a boat in the Caribbean that your friends who work chartered and allowed you to join in exchange for your services as as a reiki, bodywork, sound bath, ecstatic dance, and ‘ketamine therapy’ practitioner.
If you can’t see yourself on any of these winter circuits, you’re not the wintering type, and that’s totally ok.
Indianapolis isn’t as bad in the winter as the death toll suggests, and the week you’ll spend in the Florida Keys will be just as memorable as the week you spent there last year and the year before that.