How to Spend a 3 Day Weekend in Aspen

We traveled to Aspen in mid-December for an adult-only three night vacation. We have taken this trip a couple of times before and although I do always wish I had just one-more-night; three nights really is enough to fly in and have a great time! I will give you the lowdown on what we did on our three nights in Aspen as well as where we ate, drank and skied. If you are looking for a weekend of fancy, fun and skiing with friends; Aspen is the place to go. We were lucky enough this trip to have enough snow to ski, but the conditions definitely weren’t great and a lot of the runs weren’t open yet. That is the chance you take when you go as early as we do in the season.

Where to Stay in Aspen

We flew into Aspen airport on a Thursday and I love that it is only a quick 15minute Uber/Taxi ride to downtown Aspen. We stay at a little hotel right in the middle of town called the Independence Square hotel. This is an old tradition and it is definitely not a fancy spot, but the location is wonderful and it does the trick. They are one bedroom/one bath units with a small lobby area with a kitchen where they serve a little continental breakfast in the mornings. It is also conveniently located across the street from the bus station that you can take to the 3 other ski mountains close by and it is only about 2 blocks away from Aspen mountain.

There are plenty of hotels to choose from in Aspen and many that have good locations. We have stayed at this Hyatt Grand before and this was nice because they have condos that range from studios to 4 bedrooms. Other hotels that are close to the mountain and have more of a fancy hotel vibe would Little Nells, W Hotel and the St. Regis. I have been to all of them, but never stayed at any of them. Another gorgeous and iconic hotel in Aspen is the Hotel Jerome. It is a must-see but is located quite a few block from Aspen mountain so not a top hotel during ski season in my opinion.

When we arrived our first day, we checked into our hotel and then headed to one of my favorite spots, the French Alpine Bistro, which is a tiny little spot that makes you feel like you have transported to a cabin in the French Alps. We had apps here for a late lunch and had one of my favorite Aspen Mindset cocktails. From there, we went back to the rooms to unpack and do a quick change for drinks and dinner. We went to the Hotel Jerome for drinks and then headed to the Caribou Club for dinner.

I can’t handle the prom poses, ha!

For our first day of skiing, we skied Aspen Mountain. As I mentioned, the ski conditions weren’t great so a lot of the runs were not opened yet; but we made the best of it and had fun skiing the runs that were open. We had lunch at the top of the mountain and they had live entertainment outside to listen and enjoy with a fun little dance party!

We went straight from the slopes at the end of the day to the W Hotel for Apres Ski. It wasn’t as lively as it can be sometimes; but since we were a group of 12, we knew how to bring our own fun!

We headed home to shower and get ready for the evening. Friday nights agenda was drinks at the St. Regis hotel and then dinner at Cache Cache. The beauty of downtown Aspen is how easy everything is to walk to. Everywhere we went for the weekend was walkable except for when we to Highlands Mountain to ski which we took the bus.

For dinner, we walked to Cache Cache which has been in Aspen for almost 4o years. They serve traditional Colorado meat dishes, a few great seafood choices and a couple of homemade pastas. I had the cacio d Pepe and it was delicious.

Saturday we headed over to Highlands Mountain to ski. It was opening day for the mountain and thankfully they had several runs open, but a lot of the mountain was still closed due to lack of snow. We skied all morning and then had a reservation to stop for a late lunch at Cloud Nine on top of the mountain.

Cloud Nine is an incredible experience and quite wild and frivolous!!! They are known for their party and champagne spray. So, to eat inside, they have two seatings each afternoon at 11:30am and 1:45pm and you need to make a reservation. For the later seating, you have a fixed menu and they have a champagne spray after party. It’s wild, fun and last about 45 minutes!! You stand on your chairs and the music rocks and everyone is just spraying champagne all over the restaurant. I highly recommend that you wear some type of goggles and bring a plastic garbage bag to put your ski jacket and gloves in to keep dry because you still have to ski down the mountain after this party is over!!! This is quite the experience, but I will warn you it is very expensive.

In years past, we have stopped at Cloud Nine and just sat outside on their porch and enjoyed the scenery and drinks and just peeked at the craziness inside through the windows and it will cost you a LOT less money.

I am proud to say we all made it down to the bottom of the mountain safely with no injuries!!!

When we got back to Aspen, we did a quick shower and change so we could catch the festival happening in downtown Aspen. They had a big bonfire on the football field right in town and then we walked over to the mountain and they had a beautiful fireworks show.

For our last night we stopped for drinks at Hooch and then went to Jing for dinner. This asian fusion sushi bar was a must-visit in my opinion. I loved this spot!! It was such a vibe and the owner (or maybe he just works there) comes around to tables and serves “motherfucka” shots out of a bottle right into your mouth!! Its hilarious. He counts 1 moutherfucka, 2 motherfucka, 3 motherfucka as he’s pouring it in your mouth to see how long you can go! We had mostly sushi at my end of the table, but everything looked delicious.

Sadly, Sunday was our last day and time to head home! It was a trip to remember and I always leave Aspen with a special feeling in my heart. It is a great place with lots of good memories.

I hope this is helpful and if you have any favorite places to go while you are in Aspen, please share them in the comments!!

Also, I just realized that I didn’t mention any shopping on this trip!! Since we did only have 3 days and we love to ski, we didn’t make time for shopping this time, but Aspen has some absolutely amazing shopping and its worth making the time for it.