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In the annals of luxury, Aspen is one of the iconic legends. The name alone evokes a life of beauty, adventure and ease. But is the luxury hype about Aspen still true today? We decided to investigate. Here’s how to have a luxurious vacation in Aspen right now.

does Aspen still live up to the hype?

Luxury Legends is an occasional series here at Dandelion Chandelier that assesses whether an old-school luxury establishment or destination is still maintaining its traditional high standards. Or whether its resting on its laurels. In which case you can skip it. Because being a legend means keeping it fresh.


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So does Aspen, Colorado, fabled ski destination for celebrities, business moguls, and those who hope to hang around with them or become them, still measure up?

We have friends who swear by Vail, Telluride and Deer Valley. But there’s just something about Aspen that seems to epitomize the glamour of skiing Out West. After the first snowfall and before the start of the high season, we took a trip to investigate.

So does Aspen still live up to expectations? And how can you have the best luxury vacation in Aspen? Let’s find out.

How to find true luxury in Aspen

1. Where to stay: The Little Nell

After some discussion about various properties, our travel agent booked us into The Little Nell, which is the only 5-star 5-Diamond hotel in Aspen, and is ski-in, ski-out. The other two properties we considered were the St. Regis and the Jerome. More about both of them in a moment.

Upon arrival at the airport in Aspen, we were greeted by a staff member from The Little Nell who was driving one of the resort’s fleet of steel grey Audi SUVs. He took our bags and in only 15 minutes or so, we were pulling into the hotel driveway.

From the outside, for a hotel that garners such rave reviews, it doesn’t look like much: it’s a reasonably non-descript 4-story structure that nestles at the base of Aspen (also known as Ajax) Mountain.

But the lobby is warm and charming – it was beautifully decorated for the holidays. Our room was on the fourth floor, and had a spectacular view of the mountain, the lift, and the hotel pool. We had a balcony, a fireplace, a dining room/work table and plenty of room to spread out. So far, so excellent.

Is the luxury hype about Aspen still true today?

Is the luxury hype about Aspen still true today? The lobby of The Llittle Nell, Aspen.

2. Rent gear, or bring your own?

We’d decided to rent all of our gear, including boots, because we didn’t want to travel with our own, and didn’t want to risk shipping everything ahead. Four Mountain Sports has nine locations in town, one just across the street from The Little Nell.

We were impressed with the quality of the rentals available. And when we asked about skis designed especially for women, the representative upgraded us to a higher level rental for free so that we could test the newest K2 skis for women (they were great). The boots were Technics and the helmet was a brand-new Giro. And the rental process took no more than 15 minutes. Loved that.

3. First evening: Wander through the town

We went exploring on foot – one of the many charms of Aspen is that it is a very walkable town . The streets are a perfect grid, it’s impossible to get lost, and everything is pretty much a 10-minute walk from everything else.

Explore Books

Our priority was checking out the town bookstore, and we weren’t disappointed. Explore Books on Main Street is one of those lovely cozy establishments that you can get lost in for hours.

The staff has detailed knowledge of all of their inventory, they clearly love books and read a lot, and they were terrifically helpful in getting some of our Christmas shopping done.

Paradise Bakery

As we walked back to The Little Nell, the holiday lights were coming on all over town. The streets were just crowded enough. We grabbed a carrot cake square to bring back to our room from the Paradise Bakery (it was mad crazy good). After dinner at the Ajax Tavern – known for its burgers, but a fine choice for anything that could be described as comfort food – we were out like a light.

The next morning, we had breakfast in the hotel’s main restaurant, Element 47. It’s sleek and modern, and also small-scale and intimate – like many of the other elements of The Little Nell, it feels like being in the home of an elegant and gracious friend. The breakfast buffet has every item imaginable. By the second morning, the entire staff knew our names and what we wanted to drink (really hot coffee, and plenty of it, please).

4. How is the skiing?

Then it was ski time. All of our rentals had been delivered straight to the hotel so we never had to touch them. The hotel’s ski concierge took our already-warmed ski boots and helped us put them on, handed us our helmets and then sent us to the front of the hotel, where our skis, poles and ski teacher were all waiting for us. That’s as hassle-free a morning as we have ever had at a ski resort.

Is the luxury hype about Aspen still true today? 

For those who haven’t been there, one of the many beauties of Aspen is that there are four mountains within easy range, each with different features. Ajax is for intermediate and experienced skiers; Buttermilk is ideal for beginners and intermediates; Aspen Highlands and Snowmass both have varied terrain and back country opportunities. So you can easily spend a week here and never get bored. And as your skills and confidence grow, there will always be a new mountain or a new trail waiting for you.

How to have the best luxury vacation in Aspen: The gondola on Ajax Mountain, Aspen.

Our teacher was terrific – we skied 6 hours a day, and we learned a lot from him. We’re used to skiing in New England, and it really is a different experience Out West. People say that once you’ve skied the Rockies, you won’t want to return to the East, but we disagree. We love them both, for different reasons, and we’ll definitely be doing both in the future.

5. Time for some designer shopping

But back to Aspen. ALL of the major European designers have stores there, with the exception of Chanel. Most of the boutiques are located on South Galena Street. So you can ski all day, and then visit Dior, Valentino, Gucci, Dolce & Gabbana and Louis Vuitton (can we just say, this is our definition of paradise?)

Even better? The stores are not the typical “resort” stores that stock only handbags. We visited all of the above, and they had a deep and varied assortment of ready-to-wear, shoes, bags, and other accessories. And the salespeople were all incredibly friendly.

Is the luxury hype about Aspen still true today? 

Is the luxury hype about Aspen still true today? The Valentino boutique in Aspen, Colorado.

6. The best places for dinner

Over the course of our visit, we had dinner at Acquolina Trattoria, Cache Cache and Element 47. They were all outstanding and there were at least five other places we wanted to try for dinner that we just didn’t have time for. If you’re looking for a noisy, happy après-ski bar, Chair Nine at The Little Nell will suit you – it was jam-packed every night of our stay.

How to have the best luxury vacation in Aspen: Dinner at Element 47 at the Little Nell in Aspen.

The staff members at these restaurants were also incredibly nice. You can get a good sense for a town’s character by how you’re treated randomly by others. We think the best test of how well a ski resort is run is how engaged the lift operators are with the guests and the other staff members (if they’re zoned out or cranky, there’s a problem). On both counts, the vibe in Aspen is among the warmest and best we’ve experienced. It could be the legalized marijuana, but we don’t think so.

3. Where to stay: thoughts on the St. Regis and the Jerome

What about the other hotels? We ventured into both the St. Regis and the Jerome, and here’s our take.

The Hotel Jerome

The Jerome is located on a very busy street, and is very “Old West,” both in terms of vibe and architecture. Two men seem to stand guard in front of the hotel at all times, and they wear black cowboy hats, which we found rather off-putting. But maybe that’s your thing.

Inside, there’s an internal atrium that allows in lots of natural light, which is needed because the decor is dark wood, Tiffany-style lamps, and other accouterments that you would expect from a really old pioneer hotel. It has three restaurants—J Bar is highly recommended for après-ski. For us it would be a great stop for a meal, but it would not be the right place to stay – but you might love it.

The St. Regis Aspen

On the other side of town, the St. Regis is gorgeous and quite large. Walking into the lobby feels like walking into a grand European hotel. The architecture is Gothic, which is both impressive and imposing. When we visited, the lobby and surrounding areas were full of people, many with young kids. There’s a large outdoor courtyard in the center of the hotel that hosts a huge Christmas tree this time of year.

How to have the best luxury vacation in Aspen: The St. Regis Aspen. Courtesy Photo.

The holiday decor inside and out was stunning: there’s a gingerbread village with 20 “homes” in the main lobby (a darling three-year old girl in a red sweater tried really hard to lick one of them before her dad intervened). In another wing of the hotel there is a lounge with a roaring fire and a large Christmas tree that was inhabited when we peeked in by a man with two incredibly cute little dogs wearing plaid vests. It could not have been any more Currier & Ives. Really lovely.

Our verdict? If you are traveling with kids or a large group, or you just want to be around a lot of people, then the St. Regis is a great choice for how to have the best luxury vacation in Aspen. It can provide a high-style, grand vacation. We wanted calm and quiet on this trip, so for us The Little Nell was the answer to the question of how to have the best luxury vacation in Aspen.

how to experience a true luxury vacation in Aspen

Is the luxury hype about Aspen still true today? In our book, Aspen keeps its crown as a legendary luxury experience based on what we saw.

Last word? We discovered that it’s a fine luxury to be able to take a couple of days of “me time” before the holiday crush. We’d never done it before, never had the time, and it’s the best present we’ve given ourselves in long while. You should do it if you can. Self-gifting is totally allowed this holiday season.

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For access to insider ideas and information on the world of luxury, sign up for our Dandelion Chandelier newsletter hereAnd see luxury in a new light.

Pamela Thomas-Graham

Pamela Thomas-Graham is the Founder & CEO of Dandelion Chandelier. She serves on the boards of several tech companies, and was previously a senior executive in finance, media and fashion, and a partner at McKinsey & Co.