POV: You and your girlfriend are taking your first real trip together, and it needs to be perfect. You saw on a We Met At Acme poll (Emily made you follow) that girls love when the guy takes initiative, so this is your big chance to step it up.
In all fairness, you tried to plan a weekend in Montauk last summer and Emily sent you a color-coded itinerary planned minute by minute in military time. She swears she’s just a little bit of a control freak. You’ve never been to Aspen before (your family is more of the Beaver Creek type), so you literally have no idea where to begin. You know waffles at Bonnie’s are a must, and everybody raves about the truffle fettuccine at Casa Tua… but that’s about it.
Just in time, we’ve connected with Alexander Hankin - popular arts philanthropist, social commentator, and OG Aspen expert. Spending time at this star-studded “winter playground” for as long as he can remember, Alexander can give you the real inside scoop... not the BS you see on Instagram.
When he’s not on the slopes, Alexander is writing for leading arts and culture columns, co-chairing (and launching) the MAD Luminaries group at the Museum of Arts and Design and sitting on various boards across the arts & culture sector — Board of Directors of Opera Philadelphia, Whitney Museum of American and Art's Contemporaries Committee, to name a few.
Below, Alexander has curated the ultimate guide for a boujee winter in Aspen.
Hotels
The premier place to stay in Aspen, The Little Nell, is the only true ski and ski-out hotel in town. With beautifully appointed rooms complete with five-star luxury service, this celeb hotspot is located at the base of the Ajax mountain. Equally as fabulous is the St Regis Hotel, located down Durant Avenue. St. Regis is home to unequivocally the best spa in town with every amenity possible. The new kid on the block is MOLLIE. This boutique hotel brings elegance, and while a little further than others, it's still walking distance from the gondolas and all else.
Things To Do
While many flock to Aspen for the après-ski scene, I firmly believe that skiing itself embodies a true sense of sophistication. The area boasts four remarkable mountains, each offering its own unique charm. Snowmass, the largest and most vibrant, is teeming with energy and day skiers eager to carve out their winter adventures.
For those just starting out, Buttermilk serves as a welcoming introduction to the slopes. Then there's Highlands, home to the iconic Aspen Bowl, where you can hike breathtaking terrain and celebrate your accomplishments by dancing on tables with a glass of champagne at Cloud Nine.
But my heart belongs to Aspen Mountain, affectionately known as Ajax, nestled right in the heart of town and easily accessed via the Silver Queen Gondola. If you're fortunate enough to know a member, be sure to experience the ultra-exclusive Aspen Mountain Club for a truly unforgettable day on the slopes!
Shopping
Looking the part is half the battle in Aspen. Ski attire is essential, and there are two go-to spots for the latest styles. Fusalp is where to get a must-have ski jacket, and they just opened a brand new store located along Hyman Avenue. Gorsuch, is where you'll discover the chicest fashions straight from Europe, featuring brands like Bogner and Frauenschuh.
While high-end stores like Gucci and Dior grace the town, why not seek out unique pieces that can only be found in Aspen? Pitken County Dry Goods has a mix of well-known designers with up- and- coming brands. Their pieces showcase the epitome of western chic design, ensuring you stand out on the slopes and beyond. The Ralph Lauren boutique has made a name for itself with vintage treasures and exclusive western wear that you won't find anywhere else.
For the ultimate luxe shopping, try to snag an appointment at Chrome Hearts. No trip to Aspen is complete without a visit to Kemo Sabe, but be prepared to wait in line! Once inside, you can customize your hat to reflect your personal style, be it something simple or a statement piece adorned with diamonds and semi-precious stones. Upstairs you can find an exclusive speakeasy, a hotspot for celebrities. Even if you don’t make it to the bar, don’t miss the opportunity to grab a fabulous hat!
Bars and Clubs
As you bask in the glow of your après-ski look, Cloud Nine will be your name! After a thrilling day on the slopes, nothing beats the indulgence of caviar and fondue, followed by dancing to house music and the exhilarating champagne showers—pure bliss! Cloud Nine is the largest consumer of Veuve Clicquot in America, and honestly, it’s the only place in Aspen to truly let loose and celebrate on the mountain.
Then there’s Ajax Tavern, where the energy is electric. Picture this: DJ beats pulsating through the air, cocktails flowing freely and a vibrant crowd milling about, all while watching skiers glide down the mountain in boozy afternoon revelry. Doesn't get better than this.
But the crown jewel of Aspen’s après scene has to be The Snow Lodge. Whether it’s epic DJ sets from Diplo and Sofi Tukker in the lovely courtyard or private performances in the Supper Club, this Aspen institution is a celebration of style and excitement. Here, the incomparable Jayma Cardozo reigns supreme, curating a guest list that’s as fashionable as it is exclusive. When it comes to the best party in town, you know you’re in for an unforgettable experience at the Snow Lodge.
Restaurants
Aspen has some of the best culinary experiences in the Rockies. If you're craving sushi, you absolutely HAVE to check out Matsuhisa. They only open their reservation box one month in advance, so set your alarm for midnight and get that call in — trust me, you do not want to miss out on the best sushi in town.
If you're in the mood for some juicy perfection, Catch Steak is another must-visit. For Italian lovers, Campo De Fiori is an absolute classic. Great music, vibrant ambience and some of the most authentic Italian dishes you’ll ever have — it's a true Aspen staple that you can't miss! Wayan also just opened their Aspen outpost and brings their delightful Indo-French twist right to the heart of the Rockies. Their signature lobster noodle dish and amazing small bites are not to be missed — this place is a game changer.
When the sun sets and you’re looking for a fun late-night spot, the legendary Caribou Club is your ticket to an unforgettable night. Non-members can make dinner reservations and sneak in, but becoming a member is where the real fun’s at—trust me, you'll want to be there every night. The vibe is electric, and you never know who you might see tearing up the dance floor!
Everything Else
But Aspen isn't just about the nightlife. Dive into the culture at the Aspen Art Museum, where world-class exhibitions showcase the best of the western slope. And don’t skip the Wheeler Opera House, which boasts incredible performances from opera to theater and dance. Oh, and if live music is your jam, Belly Up is THE intimate venue to catch artists from Kygo to The Flaming Lips!
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