Holiday Travel: Doing It Right in Aspen High Life

Enjoy Aspen, Colorado During the Holiday Season

Three years ago when my son was a senior in college, he asked me if we could go skiing over his winter break. After considering different ski towns in Colorado, Utah, and British Columbia, we both decided that Aspen, Colorado sounded like a great place to start. I thought to myself; this is a great chance to redeem myself. I had been working and traveling a lot over the past year and feeling guilty as charged. I got caught up in thinking about how much fun it would be, but I forgot to ruminate about the fact that I had not been on skis for maybe 15 years.

Our family practically grew up on skis, so I was not worried. The real surprise came about while experiencing some extra-curricular activities that I will warn you about so you will not have to make the same mistake. I also am going to talk briefly about fashion, après-ski, and excellent restaurants. I wish everyone the kind of enjoyment one gets when skiing in the mountains, as there is no better way to spend the winter in my opinion.

Plan Ahead

To start things off, there are a few tips and tricks to making the Aspen trip less cumbersome on your wallets. First and foremost, you are going to want to book your flights a few months in advance; I would say three months to be safe. The reason why I say this is because the flights in and out of Aspen are on notoriously small aircraft and seating is very limited. If you wait to book your tickets until six months, you could pay over double price for airfare. Second, there are some excellent hotels in Aspen, but the location is key. You want to be as close as possible to either the bus station or bus stops because lugging your ski gear around a town with an altitude of 8,000 ft. can wear you out.


The hotel that my son and I have been revisiting for the last few years is called the Aspen Mountain Chalet, located at the base of Aspen Mountain and in the heart of downtown Aspen. This hotel offers the perfect location for various restaurants, bars, or “recreational pot shops,” if that’s your thing, of course. The Mountain Chalet offers a complimentary hot breakfast, including a continental breakfast bar. It is a real mom and pop operation and the staff genuinely want to make sure that you’re fed well before hitting the slopes. The best part is once you get off the slopes, you will find an array of homemade cookies, hot chocolate and coffee served all day long. Transitioning on, be sure to phone a few local ski shops around the time you book your flights to arrange your ski and snowboard rentals (if necessary). These rentals can get extremely pricey, even just for a few days so if you book in advance, many places are more than willing to give generous discounts. Lastly, all the mountains in Aspen are covered under one ski pass, so if you’re looking to save even more money, call ahead to Aspen Mountain or Snowmass to arrange your lift tickets. Be sure to ask for discounts because these can get very pricey as well. They do deals on group bundles and just purchasing your tickets a minimum of two weeks in advance.


Now for my favorite part of Aspen, the FASHION. One sentence can probably sum this up; I will make it short and very sweet… If you own a fur, this would certainly be the time and place to wear it. If you only have faux fur, wear it as well. It does not matter whatsoever, but it is so fun to wear the winter gear. Hot ski wear is the ticket as most of you who that ski know about something called APRES SKI. This is a get together at the end of the ski day with your “team” and a chance to meet some very interesting individuals. Mostly one plan where to meet and as soon as the 4 o’clock whistle blows, everyone meets at their favorite apres ski spot for cocktails and hors-d’oeuvre. Dinner usually follows, but not for me, not once.I was so beat that I just ate and then went to bed in an attempt to survive the next day of skiing at its’ finest.The one thing that I am going to tell you about is my FAVORITE SKI JACKET / AFTER SKI JACKET – and this jacket rocks.You will be the hit of Aspen wearing one. The website is, and you can also see them on Instagram at damianiny.


There are two safety items of interest that I will list because I do not want you to have to purchase them in Aspen because they will be pricey. First item is goggle, you will need them; no worries, you can actually buy really cool ones now. Just Google away, and you shall find. Not really what you want to wear, but save the cool sunnies for Apres Ski. The other item you must certainly need (not want but desperately need) are a pair of boots sans a leather sole, RUBBER SOLE ONLY. Take it from someone who has experienced the slippery snow on the streets and sidewalks with a leather sole. Just because they look like snow boots, does not mean they are. All I can say is thank GOD my son was holding my arm when my feet flew out under me. That would have ruined the ski trip for sure.

Drink a lot of Water

Also, if you are not accustomed to the altitude of the mountains, you may want to arrive a day early to adjust before hopping on skis and cruising up 12,000 feet back to the bottom. You need to really hydrate (with water) and walk around the town; maybe even take a ride to the top of the mountain with skiing the first day. Altitude sickness can ruin your vacation for sure and Aspen Mountain is very HIGH.


The town of Aspen itself has only 6,800 year-round residents, but during ski season it is just jumping and buzzing with people. If you are lucky enough to be there during the Holiday Season, it is especially magically with the amazing lights and décor. The shopping is abundant and upscale. There are approximately five recreational smoke shops in Aspen per se and nine altogether counting the surrounding ski areas. So, if “the SMOKE” is your thing, then you are in the right place. By the way, just a warning: those hard candies that they sell there are, well, how can I say this… they don’t affect immediately; but a couple of hours later, you might be in Pluto if you take more than 2 of these at a time. JUST SAYING, I might have witnessed or been a small part of this particular experience.


Lastly, I will touch on THREE restaurants that are my very favorite and apparently everyone else’s favorite. La Creperie Du Village is a magnificent fondue spot that you do not; I repeat do not want to miss while you are there. You will see everyone under the sun there, so make sure you must make a reservation or get there very early as they do an Apres Ski as well. The next restaurant that is very, very good is the Acquolina Trattoria and Pizzeria. The price is right, and the food is fantastic, but the place gets a little crowded so get there early as well.


Finally, the one spot that you must experience because EVERYONE, LITERALLY EVERYONE loves and visits is THE AJAX TAVERN, located at the base of Aspen Mountain right in town. If you are an A-lister or want to see some A-listers, this is a must as they all have to come down Aspen Mountain and it ends right at this eatery. The staff is wonderful and friendly, and the prices are… the prices are ASPEN, what can I say.


I hope this guide helps you all to enjoy your ski vacation and keeps you healthy enough to endure the extracurricular activities for which Aspen is so famous for. You will make a lot of life-long memories here or anywhere you go that has a snowy mountain. In fact, I am just a little older now, and I actually preferred to ski SNOW MASS, which is a short 20-minute bus ride from Aspen Mountain. It has some lovely blues and greens that start at the very top and take you to the very bottom. Yes, you can ski the whole mountain without one mogul – you read this right, and it is very rare. The Mogul says may be over for me, but one thing is for sure… I am far from done with the High Life of Aspen, Colorado.

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