Aspen vs. Vail: A Tale of Two Alpine Paradises for Skiing, Dining, and Luxury Living | ICONIC LIFE

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Aspen vs. Vail: A Tale of Two Alpine Paradises for Skiing, Dining, and Luxury Living

Skier Aspen

Tyler Wilkinson-Ray

Team Vail or Aspen? Whichever spot you fancy, here are the best-of-the-best recommendations for each skiing destination

Think of the glamorous town of Aspen as the Yankees vs. the fun-loving Vail, the Red Sox, or the Rolling Stones (Aspen) vs. the sing-along Beatles (Vail); whichever side of the fence you may fall on, know that you will most likely be cherishing every moment in either locale.

This alpine sibling rivalry between the older Aspen (born 1946 when lift tickets cost $3.75) and the younger Vail (born 1962 with a $5 lift ticket) has been in effect since the two saw each other taking turns on the Rocky Mountain slopes. With annual visitors of 1.4 million in Aspen and 1.3 million in Vail, the demand for these ski destinations is at an all-time high. 

Concurrently, with annual skiing revenue in Colorado at $4.8 billion, there has never been such an enormous diamond-shaped snowflake floating in the air.

Eric Dunn

Fortunately, we are the beneficiaries of this debate. The dedication to offer the snow-devout the best experiences possible is top of mind at both locations. Whether it’s powder day skiing, endless runways to display your best self to the well-booted set, or world-class cuisine (both towns have Michelin-star restaurants), these two skiing destinations have you covered.

You may also like: Hit the Slopes in Style at These Elite Ski Area Destinations


Vail snowy mountains

In 1962, famed Colorado 10th Mountain Division veteran Pete Seibert had an idea. How do you create a world-class ski resort on the patch of Forest Service land now known as Vail? (The town was named after Charlie Vail, the highway engineer of I-70 in the 1940s.) Fast forward 61 years and Seibert’s dream-come-true is now considered “steezy” (effortlessly stylish). 

This modern mix of style and ease is encapsulated in the quaint assortment of quality restaurants, whimsical galleries and designer boutiques in this mountain paradise. You can find your Warren Miller moments skiing the famed Back Bowls or get your turns on any of the 195 runs available. 

Vail colorado

Max Ritter

Insider tip: If you want to “feel the burn,” go for the 4-mile Riva Ridge. Whatever your fancy, this famed ski destination has something for everyone to ski, board or gawk.


Gorsuch: Gorsuch opened as a gas station in 1966. What started as a hub for fuel blossomed into the flagship store for fashionable ski apparel, gifts and ski rentals. The Gorsuch family has outfitted and decorated the Vail Valley for decades with its fashion and knick-knacks. Mrs. Gorsuch still helms the store five days a week.

Res Ipsa: This shop sells upcycled vintage denim, needlepoint loafers and custom totes embroidered with “Noblesse Oblige” for the grocery run.


Sweet Basil: Sweet Basil is the newly recognized Michelin-star restaurant in Colorado and is the go-to for its delectable cuisine. The Miso Ramen bowl makes you forget your fatigue from the slopes and will get you feeling warm, relaxed and replenished.


Gravity Haus: This state-of-the-art spa in Vail is a new addition to the town with a salt room for elevation acclimation and a cold plunge pool to revive those mogul-bruised knees.


The Sebastian: This lodge could make you a believer in the power of place. Situated away from the commotion of the gondola, you can relax and indulge in any of the three on-property restaurants. There also is a cozy library lounge in which to enjoy some downtime. And, most importantly, there are three outdoor soaking tubs with a view of tomorrow’s best corduroy as your backdrop. 

Ice rink in Vail

David Neff


Gib Singleton: Gib Singleton’s gallery has an incredibly evocative David Yarrow photography exhibit that features everything from the maw of an Alaskan Grizzly to Gerard Butler and Cara Delevingne cutting cards in a Leadville saloon. 

You may also like: The Ultimate ICONIC Ski Trip Guide 2021


Aspen Colorado

Jack Affleck

It was the dream of silver that turned Aspen into a golden reality. In 1870, the first miners scoured the land in search of fortune, but little did they know that the real cache was above ground. So, in 1940, the ambitious trio of dreamers—Walter Paepcke, Friedl Pfeifer and Herbert Bayer—created Aspen, turning the mining town into an international skiing destination for the global elite.

For skiing, Aspen Mountain is divided into the main mountain Ajax (accessible to all levels of skiers), Aspen Highlands (expert terrain) and Buttermilk (kiddo’s playground). For the powder-hungry, make the trek to Snowmass just down the road for an additional 94 bliss-filled runs.  

Ski lift Aspen

Sam Ferguson


Pitkin County Dry Goods: This store was opened in 1969 by Don Fleisher to bring contemporary clothing to the quaint town. It has been in the family for over 50 years, and you can now adorn yourself in A.P.C. and Dries Van Noten.  


Bosq: Bosq is a newly minted Michelin-star restaurant. Chef Barclay Dodge never fails to impress with an evolving menu showcasing the valley’s quality ingredients with inventive takes (think Forest Broth).

Ajax Tavern: After attempting a new land speed record while bombing down Ajax, there is no better place to watch other skiers than at Ajax Tavern at the base of Aspen Mountain. Important note: truffle fries are mandatory.


Viceroy Snowmass: Place the kids in ski school, turn off the phone and immerse yourself in this 7,000-square-foot spa with offerings that include the 120-Minute signature Champagne Indulgence.  You begin with bubbly in the bath, you then receive a full body shea butter wrap while relaxing with a deep tissue scalp massage. 



Aspen XO House: This Scandinavian-inspired home can sleep eight, is dog friendly and might make you reconsider life’s priorities with its elegance and comfort. You will be the envy of many, as only the cognoscenti is aware of this gem. 

Aspen Art Museum: This world-class local museum is free and open to the public. The Aspen Art Museum showcases top-shelf exhibits such as the not-to-be-missed John Chamberlain retrospective “The Tighter They’re Wound; The Harder They Unravel.” You can debate and digress at the rooftop cafe, The Slippery Slope, no skis necessary.

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