The Perfect 3-day Ski Itinerary in Aspen, colorado
Affiliate Disclosure: Some of the links in this post are affiliate links, which means I may earn a commission at no extra cost to you. Your support helps me keep sharing my adventures and tips!I’m so excited to share today’s travel post! Aspen, Colorado, is one of my favorite places on earth, and you don’t have to be a gazillionaire to enjoy a three-day ski vacation!
So, if you’re craving a ski getaway that mixes thrilling slopes, super delicious food, and that relaxed Aspen vibe, then you’ve come to the right place. My husband and I just got back from our annual 3-day winter trip to Aspen, and I can’t wait to share because you’re going to want to book your trip asap.
From checking in at our cozy hotel to drinks at the historic Hotel Jerome, from epic skiing at Snowmass and Aspen Mountain to a final breakfast at a charming Italian café—this itinerary has it all.
Ready to see how you can make the most of your Aspen adventure? Let’s get to it!
Day 1: Check-In, Hotel Jerome, Window Shopping & Dinner at Madame Ushi
Welcome to Aspen
After arriving in Aspen (we drove since we live two hours away in Breckenridge, but Aspen has its own airport), we checked in to our hotel and immediately felt the magic of this mountain town. Aspen has a unique charm that instantly makes you feel relaxed yet excited for the adventure ahead.
What we did on Day 1:
Aspen Square Hotel check-in: We have stayed at this hotel twice, and it is one of our favorites. It has a covered parking garage, heated pool, hot tub, a workout room, and balconies to sip coffee or wine with a view of Aspen Mountain. The rooms are independently owned, so each room is different; however, they all have a kitchen. They are open-concept with one bedroom, so for families, this might not be the best option.
Drinks at Hotel Jerome: Our first stop was the legendary Hotel Jerome. I’ve always been a fan of places with history and character, and Hotel Jerome is just that. The bar has a laid-back yet chic vibe where we were able to people-watch the ladies in their fur coats and overall fanciness. Hotel Jerome has a great wine list- I had a glass of Super Tuscan. Tim said their Bourbon list was fantastic- he had a Weller Special Reserve. If it’s your first trip to Aspen, Hotel Jerome is a great place for breakfast too!
Window Shopping: After our drinks at Hotel Jerome, we wandered around downtown Aspen. The mix of upscale boutiques, art, and fun local shops made for the best kind of window shopping. I loved checking out unique finds—from designer accessories to locally made treasures. If it’s your first trip to a mountain town, make sure to check out Kemosabe. It’s an upscale western ware, cowboy boot, and hat shop that has the most electric vibe. You can also get yourself a glass of whiskey while you shop!
Dinner at Madame Ushi: As the day turned into night, we headed over to Madame Ushi for dinner. This isn’t your typical restaurant—it’s a Japanese spot that doubles as a nightclub. The ambiance is moody and cool, with dim red lights and a buzz that’s equal parts fancy and fun. While the food wasn’t my absolute favorite (I’m all for trying new things, though!), the whole experience was memorable and definitely a conversation starter.
Hotel Jerome
The Day in Detail
I’ve got to say that starting your Aspen trip with drinks and a bit of retail therapy is the perfect way to ease into vacation mode. Remember, Aspen is at 7,000ft elevation, so if it’s your first time here, you’ll want to make sure you are hydrating and taking it easy. Altitude sickness is a real thing, and it’s not a joke.
Here’s a quick rundown of our Day 1 highlights:
Hotel Check-In:
Cozy rooms with stunning downtown views
A warm, inviting atmosphere that made us feel right at home
Historic bar with a cool, retro vibe
Creative cocktails and relaxed conversation that set the tone for our trip
Window Shopping:
Strolling through Aspen’s downtown streets, discovering unique boutiques
A mix of high-end stores and charming local shops that cater to every taste
Dinner at Madame Ushi:
A unique blend of Japanese cuisine and nightclub energy
A fun, swanky environment that’s perfect for a memorable night out
Day 2: Hitting the Slopes at Snowmass, Lunch at the Alpin Room & Dinner at Monarch’s Steak House
Morning on the Slopes
We came to Aspen for a ski vacation, so on our first day on the mountain, we headed over to Snowmass—a ski area just 15 minutes from downtown Aspen that offers something for every skill level. Whether you’re a beginner or a seasoned pro, Snowmass will have you grinning from ear to ear as you carve through the fresh powder. This is such a great ski mountain!
Our morning adventure at Snowmass included:
Skiing:
We spent the morning skiing and enjoying the fresh powder after a recent snowstorm!
There are beginner to expert trails at Snowmass, so you can find the perfect run for any skier.
Quick Tips for Snowmass:
Make sure you’re geared up for all conditions—it can be a mix of fast runs and mellow glades.
If you’re new to the area, check out some of the beginner-friendly runs before exploring the more advanced terrain.
Snowmass has a laid-back vibe that makes it ideal for a day of both serious skiing and casual fun. We enjoyed skiing over at Elk Camp, High Alpine, and Big Burn. Hanging Valley is popular, but it’s all double black, and since I’m not that badass, Tim has to wait until next time😉
Lunchtime at the Alpin Room
After working up an appetite on the slopes, we made our way to the Alpin Room for lunch. Tucked inside the High Alpine ski lodge, the Alpin Room serves up Alps-inspired dishes in an atmosphere that’s both fancy and relaxed.
What to Expect at the Alpin Room:
Atmosphere:
Bright, inviting dining room with cozy touches like faux fur-covered chairs that add a touch of Aspen charm.
A mix of modern elegance and rustic comfort that makes you feel like you’re in the heart of the mountains.
The Food:
I opted for a hearty bowl of mushroom sausage stew paired with a glass of Chablis—it was so good!
Tim chose a fresh chicken salad that looked as good as it tasted and a Peroni.
We had coffee and German Chocolate Cake for dessert.
Pro Tip:
If Swiss cuisine isn’t your thing, don’t worry—the lodge’s cafeteria also offers huge, satisfying pretzels, creamy cheesecake, and an awesome selection of wines, beers, and sparkling wines, plus other ski fare. The food at the Snowmass ski lodges is top-notch!
Dinner at Monarch’s Steak House
After a full day on the slopes, a relaxing lunch, and an after-ski nap, we were ready for dinner. We chose to eat at Monarch’s Steak House again (we’ve been twice), and as usual, it did not disappoint. This classic American steakhouse is a must-visit if you’re in Aspen, serving up great steaks in a cozy, no-nonsense setting. Plus, unlike many restaurants these days, it’s not super loud, so you can have a conversation!
Highlights of Monarch’s Steak House:
Ambiance:
A warm, inviting space that feels like an old-school steak house.
The kind of place where you can kick back, relax, and enjoy good food in great company while receiving great service. The wait staff is always excellent!
The Meal:
We started with a shared platter of fresh Hood Canal oysters (our favorite). I paired it with a glass of Sancerre, and Tim had a beer.
We shared a table-side Ceasar, which was excellent. But, the star of the show was the ribeye steak—cooked to perfection and bursting with flavor. And the fries were delicious! And let’s not forget the bottle of Côte Rôtie!
For dessert, we couldn’t resist a rich, decadent chocolate cake paired with a side of ice cream.
Why You’ll Love It:
It’s the perfect spot to unwind after a day on the mountain.
The menu offers a mix of familiar favorites and delicious surprises that make every bite memorable.
Day 3: Skiing Aspen Mountain, Breakfast at Bonnies, Lunch at The Butcher’s Block, Dinner at Ellina
Start Your Day Right: Breakfast at Bonnies
There’s no better way to kick off your day skiing at Aspen (also known as Ajax) than with breakfast at Bonnie’s. After you ride the Silver Queen Gondola up, ski down to Bonnies for a true mountain breakfast. I loved that they had a pot of hot wine sitting next to the coffee. I was like, oh, this is Aspen. 🤠
At Bonnie’s, you can expect:
A Cozy Atmosphere:
The vibe is casual, friendly, and totally relaxed—an old-school ski lodge.
The Menu:
I went for a classic combo of eggs, breakfast potatoes, and toast with a hot chocolate.
Tim had the meat omelet and breakfast potatoes.
Why It’s Awesome:
It’s the perfect fuel for a day of skiing, and the views are incredible! Check it out in the afternoon for happy hour, and you won’t be sad you did!
Hit the Slopes at Aspen Mountain
After a satisfying breakfast, we hit the mountain. It was a bluebird day and absolutely fantastic! Aspen is known for its more advanced terrain—perfect if you’re looking for a bit more challenge on your ski adventure.
What to Expect on Aspen Mountain:
Thrilling Runs:
Aspen offers steep, fast-paced runs that get your adrenaline pumping.
It’s a playground for those who love a challenge and want to test their skills on more advanced slopes. I can ski almost anything, but I wouldn’t call myself an expert. Tim is an expert skier, and at Aspen, we found runs we both really enjoyed skiing together.
Breathtaking Views:
The views from the top are simply incredible. Even if you’re not skiing, the gondola ride-up is a must-do (during all seasons) for the sheer beauty and tranquility it offers.
A Unique Experience:
There’s a cool, urban feel to Aspen Mountain since it’s right in the heart of Aspen.
It’s a nice contrast to Snowmass's larger, sprawling slopes, offering a more intimate and energetic vibe. We talked to a local who said he didn’t even know what a lift line was. The mountain didn’t feel crowded, and we never had to wait in line. I’ll take it!
Refuel with Lunch at The Butcher’s block
After an epic morning on Aspen Mountain, we needed to EAT. We stopped at The Butcher’s Block. This butcher shop was AMAZING! They have all cuts of meat, seafood, cheeses, and a deli. It’s located across the street from our hotel and the mountain, and it’s a must-visit stop while you are in Aspen. We had lunch, and then the next morning, before we headed home, we stopped in to buy ribeyes, shrimp (which were the best I’ve ever had), arugula, and some fancy butter. The Butcher Shop ships, so you can check them out.
What to Love About The Butcher’s Block Deli:
Simple and Amazing:
I went for an egg salad with chips and a Pepsi—like, the best lunch in the Universe, am I right?
Tim had a French dip that ended up being his favorite meal on our trip! It’s that good.
We sat outside in the sunshine, and it was absolutely marvelous!
Local Favorite:
I loved that everyone was chatty. We met a local woman, who was the sweetest ever, and her adult daughter. She travels back and forth to Aspen every two weeks from Florida on her own plane, depending on the weather and if she wants to deal with the snow. Totally Aspen.
Afternoon Window Shopping in Downtown Aspen
With our bellies full and the afternoon stretching out before us, we decided to indulge in a little more window shopping. Aspen’s downtown is a treasure trove of unique boutiques, stylish stores, and quirky local shops. Whether you’re in the mood for designer finds or just a fun stroll, the streets of Aspen have something for everyone.
Our Window Shopping Highlights:
Unique Boutiques and Art:
My favorite spots are Pitkin Country Drygoods, Ralph Lauren, Citizen of Humanity Jeans, and Ute Mountaineer. I love going into Ralph Lauren and pretending I live there. It’s decorated so gorgeously, and you can get a cup of hot chocolate while you shop. Did I mention how much I love Aspen?
You’ll see sculptures all over downtown Aspen. They add charm, sophistication, and an overall cool vibe. There are plenty of art galleries, too. I love to browse all of them.
Dinner at Ellina: A Cozy Italian Finale
As the day started to wind down, we headed to dinner at Ellina, an Italian restaurant that perfectly wraps up your Aspen experience. Ellina offers a warm, inviting setting with delicious Italian fare that feels both familiar and delightfully different. We’ve eaten here several times and it’s always delicious with great service.
Why You’ll Love Dinner at Ellina:
Homestyle Italian Cooking:
The menu features hearty pasta, savory sauces, and a fantastic selection of Italian wines.
I opted for the bolognese, while Tim went for the salmon—both dishes were cooked to perfection.
Relaxed Ambiance:
The vibe is casual yet elegant, with friendly staff that makes you feel right at home. The stonework inside the restaurant is beautiful and makes you feel like you're in Italy. It’s very Aspen!
Perfect Ending:
After a day full of adventure, dinner at Ellina felt like the perfect way to cap off your Aspen story. If you aren’t in for dinner, check out their bar. It was hopping with locals, but by 7pm had cleared out. We are going to check that out on our next visit.
On the Way Home: Breakfast at Sant Umbroeus
On our way home, we stopped at Sant Umbroeus for breakfast. This charming Italian café is the ideal spot to wrap up your trip with a final taste of Aspen’s culinary delights. It’s very Italian inside, with little tables and chairs, a modern design vibe, and a fantastic pastry case!
Breakfast at Sant Umbroeus:
Amazing Breakfast:
I had berry ricotta toast, which might be my favorite sweet breakfast ever. I also treated myself to a delicious glass of Prosecco.
Tim had the avocado toast with lox and a chocolate croissant.
The chocolate croissants were so good, that we ordered two more and ate them on the way home.😜
While we were waiting for our breakfast, we ran into our friend Ben from college and his wife. How cool is that? We enjoyed our breakfast together and had such a nice visit. It was a great way to cap off four trips to Aspen.
Your Aspen Adventure Awaits
I hope this detailed 3-day itinerary gives you a taste of what Aspen has to offer. Every day was packed with fun, food, delicious wine, and time together as a couple—we don’t get enough of that! Aspen is one of those rare places where adventure meets relaxation, and every experience—big or small—adds up to a journey you’ll remember for a lifetime.
Ready to Make It Happen?
If you’re pumped up and ready to experience Aspen for yourself, here are a few quick steps to get you started:
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Final Thoughts: Aspen Is Waiting for You
There’s something truly special about Aspen—a place where the slopes are thrilling, the food is divine, and the vibe is as chill as it is inspiring. Every moment of our 3-day trip was filled with little surprises that made me fall in love with this mountain town all over again. Whether you’re a hardcore skier, a foodie looking for the next great meal, or someone who just loves a good adventure, Aspen has something that will speak to you.
I truly believe that Aspen is more than just a ski destination—it’s a lifestyle. It’s about discovering the perfect balance between adventure and relaxation and making memories that remind you why travel is so magical.
Thank you for joining me on this journey through my Aspen itinerary. I hope my stories and tips inspire you to create your own adventure in this incredible town. Now, it’s your turn to hit the slopes, enjoy the local eats, and discover the magic of Aspen for yourself.
Cheers,
Courtney
If you liked this post, make sure to check out my 5 Essential Tips for Visiting Yellowstone!
