What billionaire summer camp looks like in winter
Travelogue: Highlights from Sun Valley, Idaho and...Zeitgiest-y
I was talked into Idaho.
Early in the ski season I was determined to duplicate my 2024 solo snowboard trip to Jackson and Big Sky.
But then, my curiosity piqued when I was told Sun Valley was “chill,” had a “great vibe,” and was in the Ikon network.
Until recently, my limited knowledge of the place was that it’s where a bunch of billionaires like these titans of media and tech go for Allen & Co.’s annual summer retreat.
Apparently, the town was chosen specifically because its location offers unrivaled discretion and privacy away from crowds.
Ultimately, it came down to rental home availability.
I’m Shindy. I sold my financial content company and now I write this weekly culture, money, and lifestyle Substack. I’m a journalist and bestselling author featured in Forbes, The Wall Street Journal, Business Insider, Bankrate, Cheddar TV, and HuffPost. If you haven’t yet, and would like to join more than 7,200 people on the internet who are interested in what I have to say, then tap this button right hee-ya:
The options in Sun Valley were more appealing and waaaaay less expensive than those in Big Sky at the time, by thousands of dollars.
Last time I stayed in Big Sky, I was in a kitted-out house much grander than what Mr. Bean and I needed, but it turned out to be a little bit of a disaster because half the advertised amenities didn’t work or weren’t available (Peloton, Sonos, hot tub), and the house was the first of a new development across from the resort, which meant it was alone at the end of a dark street with barely any signage.
So, me, my ski adventure friend, and Mr. Bean started from Jackson on a road trip out west.
Along the way, we stopped in Driggs for a skijoring event, because why not?
Skijoring is like water skiing, but instead of a boat it’s a cowboy on a horse towing a skier or snowboarder, fast, over hills and cars.
Just as fun was the mud and the people watching, the cowboy cosplay, and vendors offering everything from fur coats to candles.
Upon arriving in Sun Valley proper, the first stop was, of course, the lodge.
You’re welcomed in by a cozy lobby fireplace and just as you orient yourself, you turn right or left down the main hallway and take in all of Sun Valley’s history.
To establish Sun Valley as a luxurious ski resort, celebrities were flown in for photo shoots on the mountain.
The resort’s cachet was the brainchild of business tycoon W. Averell Harriman who, with the help of a New York PR wiz, transformed it into a glamorous, modern ski destination.
Seriously, the campaign included flying out Hollywood stars like Clark Gable to pose on the ski mountain, and even Ernest Hemingway finished “For Whom the Bell Tolls” here.
My rabbithole-ing told me that after Key West, Hemingway lived out his days fishing and big game hunting here, where he’s also buried.
As for the winter conditions, well I happily got a taste of spring snowboarding in late February.
The lifts were never busy or crowded, and I felt that magical combo of wonder and fear when you’ve got portions of entire runs all to yourself.
The lodges themselves are spectacular: Sky-high ceilings and massive fireplaces — these were some of the nicest looking lodges I’ve ever seen; rustic and traditional without being cheesy or dated.
The people who visit Sun Valley for skiing and snowboarding, on the other hand, are noticeably older and less aggressive than those in Jackson.
As for the mountain itself, it offered nice challenges and long (and I mean 3+ mile-long) groomed runs.
I used AI to navigate the slopes
Every time I’m on a new mountain, I hire a guide to show me around and give me a lay of the land.
This saves me time in getting acquainted with new terrain and navigating the mountain.
One day I also had AI make an itinerary for me:
By the way, if you’re curious about what AI prompts are proving most effective in my day-to-day consulting work or personal financial admin, then hmu.
Quiet, clean, and empty by night (packed restaurants though)
Sun Valley and the town of Ketchum are picturesque, idyllic, and remarkably clean.
At night, oddly, the streets were empty of pedestrians — yet the restaurants and bars were packed.
It’s like no one walks around but just stuffs into one of these places.
While ski towns attract naturally social and chatty folks, as an introvert I found most people were normal and friendly, everywhere felt like a safe space:
Other Sun Valley Highlights
You can find more insights to some of the restaurants and meals in my February food wrap-up:
Grumpy’s: For a solid burger, fries, and punk music. And you’ll probably have to share a booth with strangers, too
Pioneer Saloon: My favorite meal of my entire snowboarding trip (Jackson included) was here. It’s also where I got a massive Idaho baked potato.
Partly because of the food, but mostly because of the ambiance from the lower level dining room.
It’s walk-ins only, so you show up and get your name down with the hostess—who manages seatings on a clipboard; no texting, very analog.
When it was time, as my friend and I were led through the main dining room to the downstairs, we felt a little FOMO at being relegated downstairs.
Boy were we wrong; in fact the only way to enjoy this restaurant is to be completely surprised and utterly delighted by the scene downstairs.
Strangers were treating each other with bottles of wine. Everyone was chatting with each other over the tables.
And by the end of the evening, I, too, gave half of a gargantuan mud pie slice to the next table over of three young cowboys. Unforgettable!Enoteca: If a 9PM New York style pizza is what you crave, then this is where to find it
Roundhouse Lodge: Though the popular thing here is fondue, my smoked trout niçoise was pretty dang tasty
Fiamma: Rabbit mafaldine! Scrumptious! Divine!
Warm Springs Lodge: I got the legendary ooey, gooey chocolate chip cookie here and I didn’t regret it
Casino: A standard billiards hall where you can tuck your quarters to claim you’re next up
Maude’s Coffee: Part of the new wave of coffee/consignment shop hybrids, this little spot was perfect for a quick cortado
Capelet Consign: A fine consignment shop with well-curated items like mules from The Row, Celine sunnies, Gucci sweaters, lots of designer ski jackets, and Hermès scarves. I found a barely worn, stylish Patagonia jacket myself for $75
What about you?
Are you excited that winter’s over? Happy spring equinox! 🌸
📺 I’m watching:
The Pitt, Max
I was a latecomer to this show and am on my way to Season 2, woo-hoo. At this point I feel Noah Wyle could probably pull off being an actual ER doctor
Age of Attraction, Netflix
Oh brother. Well, as with all trainwrecks of dating shows, I will keep my eyes plied for the finale. Also, if carnivals still had age guessers, I would be so perfect because I correctly guessed most of the contestant’s ages before their reveals
Outlander, Starz
Yawn. Let’s have dialogue over dramatic music. Then, action sequence! Then, repeat. Episode two got a little more interesting, but I’m feeling this final season to be very dull so far. Which is awful to say, because I’m a true fan! Let’s hope it stops feeling like they’re just phoning it in
📚 I’m reading:
Sophia’s been on a tear lately writing back-to-back bangers about completing her move (mentally and physically) from L.A. to London.
It reminded me: The only person who needs to understand your zeal and calling for living in faraway places and doing crazy things is…you.
In money news, if you’re curious about what’s happening in the Strait of Hormuz and how it’s impacting your wallet and investments, then here are some insights. This is merely to rabbithole and not endorse any of the ideas within:
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Until next time,
Shindy
On Instagram + TikTok
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