Aspen Itinerary – Luxury Summer & Winter Escapes Curated for You
The key to having the perfect vacation that is all at once refreshing, exciting, and educational is all in the Aspen itinerary. There is such an abundance of things to do in Aspen, Colorado, from cultural to athletic and even wellness-oriented; it can often be hard for visitors to know what to do when.
Here’s a list of topics featured in the article:
- What is the Best Aspen, Colorado Itinerary?
- Itinerary for a Winter Ski Trip
- Itinerary for a 5 Day Summer Trip
- Customizing Your Aspen Itinerary
- Start Planning Your Aspen Adventure Today!
What is the Best Aspen, Colorado Itinerary?
The ideal winter itinerary is to ski a different mountain each day to experience all the terrain that Aspen-Snowmass has to offer. In the summer, visitors normally do outdoor activities like hiking, biking, and fishing in the morning, then dedicate the afternoons to shopping, visiting museums, and going to the spa.
Itineraries look different for everyone, depending on your interests and who your travel companions are. This guide will cover all the best things to do, as well as when you should do them, so visitors can experience Aspen like locals.
Itinerary for a Winter Ski Trip
Aspen, Colorado is a skier and rider paradise! Between Aspen and Snowmass, there are 4 mountains with hundreds of runs between them.
Here is an example itinerary for a winter ski trip.
Day 1: Arrive, Explore, and Get Fitted
Explore Town & Get Lunch at Meat and Cheese
After you have arrived and unpacked, it will likely be about time for lunch. This is also the perfect time to start exploring downtown Aspen.
Your first taste of Aspen should be somewhere ultra-local, like Meat and Cheese. It is a farm shop that sells charcuterie and serves soups, sandwiches, and salads.
Gear Rentals, Tune Up, or Snowmobile Tour
After lunch, you will want to get your gear rentals or tune ups taken care of right away. If you’re newer to skiing, you’ll likely need to rent gear. If you have your own gear, it might need a tune up.
Visitors who don’t ski may want to jump right into activities by going on a snowmobile tour at T Lazy 7 Ranch. Snowmobiles are very easy to drive, so it’s an excellent family activity.
Drinks at The Living Room and Dinner at Angelos
The Hotel Jerome Living Room is a key part of an Aspen itinerary; it’s the heart of the social scene with a cozy atmosphere and simple, delicious cocktails to boot. After drinks and socializing, it’s time for dinner at Angelo’s – an elegant Northern Italian restaurant known for the curated wine list and homemade pasta
Day 2: Ski Ajax and Double Après
Ski Aspen Mountain
Skiing Ajax is not for beginners, but experienced skiers and riders will love the challenge that the mixed terrain offers. If you’re staying at The Little Nell, the ski concierge can provide you with highly knowledgeable insights into the conditions.
Double Après
Après ski is the local term for the social gatherings and dance parties that wrap up the ski day. Aspen has a robust après scene, so visitors will often hit an après party on the mountain, then ski down and get more drinks in town. Eleven212 is the biggest après destination on Ajax. Located next to the Sundeck at the summit, it pulses with live music while drinks flow.
After you ski down, you should check out The Snow Lodge, which combines old world luxury with coastal nightlife. It’s up to you if you want to change clothes or try your hand at dancing in ski boots.
Dinner at Matsuhisa and Drinks at Hooch
The Matsuhisa menu consists of traditional Japanese dishes but with Peruvian touches. You’ll also be able to sample Hokusetsu sake that is exclusively served at Nobu Matsuhisa restaurants.
Hooch is a craft cocktail bar that serves the classics, new-age drinks, and everything in between. The vibe is casual in a bespoke kind of way.
Day 3: Ski Highlands and Experience Cloud Nine
Ski the Highlands
It’s time to conquer Highland Mountain, which has some of the most difficult terrain in the whole valley. Advanced skiers and riders might want to give the Highland Bowl a shot.
The Cloud 9 Experience
You won’t need to leave the mountain or even take off your ski boots to get both lunch and après. Cloud 9 is a must-see Aspen itinerary location. When you go there for lunch, it feels like any other upscale restaurant. When après rolls around, the place transforms into party central.
Dinner at Steakhouse No. 316 then Table at Sterling
This steakhouse is located in a historic building that dates back to the 18th century. Meat lovers and steak aficionados will love the classic menu and appreciate the high-quality cuts.
The Sterling is a classic nightclub that will remind you of the Miami and LA club scenes. Visitors often enjoy getting a booth and bottle service, so they can have a VIP clubbing experience.
Day 4: Ski Snowmass and Dine at Home
Ski Snowmass then Lunch at Sam’s
On your penultimate day in town, it’s time to hit Snowmass Mountain, which is the largest of all the ski areas and has a good mix of different difficulty runs.
The best on-mountain restaurant is Sam’s, located at the top of the Village Lift Express. The menu is all Italian classics that center around warm, cheesy goodness – it’s the perfect warming break from a long day in the snow.
Après in the Afternoon and Private Dining in the Evening
You have 2 options for après ski festivities in Snowmass. There’s the Après Ski Club at Viewline Resort which feels like an open air music festival. Your other option is Bunny’s Social Club, which is a ski-in/ski-out social hub with an overall more laid back atmosphere.
For dinner, you simply must utilize the services of a private chef. If you’ve never done private dining, it makes you feel like the most important person in the entire world; if you have, then you understand the convenience and luxury of having a meal completely customized to your every wish.
Day 5: Depart
Sadly, vacation can’t last forever. Depending on when your flight leaves, you may have time to squeeze in some last minute shopping.
Aspen, Colorado Itinerary for a 5 Day Summer Trip
While Aspen is known for its legendary winters, summer in the mountains is equally magical. Visitors love the warm weather, natural beauty, and abundance of activities. If you visit in the summer, your Aspen itinerary might look a little bit like this.
Day 1: Arrive, Easy Hike, and Explore the Town
Lunch at Ajax Tavern + Explore Town
After you arrive and get settled in, it’s time to grab lunch at Ajax Tavern. This is a prime food and social scene; you definitely need to order the truffle fries. After you’re all fueled up, you should wander around town, pop into galleries, and check out the luxury shopping scene for any items that your wardrobe requires.
Afternoon Hike
Some visitors are able to acclimate to the altitude relatively quickly, while others need to ease into activity a little slower. Depending on how you’re feeling, you can pick an easier or harder trail. In general, Smuggler Mountain is a solid way to get started because it has great views and is not overly challenging.
Dinner at Cache Cache
Cache Cache is a French-American restaurant known for its lively atmosphere, extensive wine list, and consistently excellent food. It’s the kind of place where one bottle of wine easily turns into two – both of which perfectly fit your meal.
Day 2: Farmer’s Market, Mountain Yoga, and Horseback Rides
Breakfast at Jus and Aspen Saturday Market
Jus is the local health shop and juicery. The most famous parts of the menu are liquid but they also serve sandwiches.
Every weekend for the whole summer is the Aspen Saturday Market where local vendors line the streets with fresh produce, baked goods, flowers, handmade jewelry, and art. It’s equal parts community gathering and culinary treasure hunt.
Yoga, Lunch, and Horseback Riding
The next item on your itinerary is a gondola ride up Aspen Mountain. At the summit, there are mountaintop yoga class where you can breath, stretch, and lunge with an incredible view. While you’re up there, you might as well grab a bite to eat at the Sundeck, which serves American fare in a casual atmosphere.
In the afternoon, head to T Lazy 7 Ranch for a guided horseback ride. The trails wind through meadows, forests, and streams, offering a peaceful way to experience the landscape.
Dinner at Wayan and Drinks at Bad Harriett
Wayan is a new favorite among locals and visitors alike. The menu merges Southeast Asian flavors with alpine Aspen touches, which is most evident in the corn fritters and lobster noodles. For your night cap, check out Bad Harriet, which is the intimate, moody speakeasy located in the Hotel Jerome.
Day 3: Fly Fishing, Spa Afternoon, and a Night Out
Go Fly Fishing then Eat a Fish Lunch
Next up on your Aspen itinerary is fly fishing. Even if you’ve never held a fishing rod before, local guides will walk you through the basics. The Roaring Fork Valley has world-renowned fly fishing, so you’re bound to catch something. Even if you don’t get any bites, it’s a meditative way to start the day.
If fishing puts you in the mood for fish, head on over to Clark’s Oyster Bar for fresh seafood and chilled martinis.
Afternoon at the St. Regis Spa
Spend the afternoon at the St. Regis Spa. A massage is highly recommended after a few active days, but you’ll also want to carve out time for the steam room and hot tubs.
Dinner at Catch Steak and Clubbing at Madame Ushi
Catch Steak delivers a dining experience that is high energy, ultra-local, and decadent in its thoughtful preparation. Afterward, continue the night at Madame Ushi. Expect music, dancing, and a crowd that understands that Aspen nightlife doesn’t take the summer off.
Day 4: Breakfast, eBikes, and River Time
Have a Big Breakfast
After a night out, there’s nothing better than a hearty breakfast. If you prefer a savory meal, then head over to The Bear Den; the menu consists of eggs cooked every which way and healthful juices. If you want something sweet, then try Poppycock’s, which has a menu full of crepes, french toast, and pancakes with different fruit and sauce combinations.
Go for a Ride on an E-Bike
Renting an e-bike is a great way to explore town and the surrounding areas. You could go see the Maroon Bells or take the Rio Grande Trail over to Woody Creek Tavern for lunch.
Woody Creek Tavern is a rustic, down-to-earth burger joint; the enormous servings and stacked burgers will keep you fueled for the rest of your ride. If you head back toward town, White House Tavern is always a solid choice for elevated comfort food.
Afternoon Float
In the afternoon, cool off with a float down the river. You can opt for a guided rafting trip for more excitement or choose stand-up paddleboarding for something a little more relaxed. Either way, it’s a quintessential Colorado summer experience. You might even see some more fish!
Dinner at The Wild Fig
For your final night, have dinner at The Wild Fig. The Mediterranean-inspired menu is fresh, flavorful, and perfect for a lingering farewell dinner. You can order a few plates for the table and toast to a week well spent.
Day 5: Depart
As always, departure day comes too quickly. The beauty of Aspen is that it feels completely different from season to season, yet is somehow unforgettable.
Customizing Your Aspen Itinerary
There is no one-size-fits-all itinerary when it comes to falling in love with Aspen, Colorado. All travel plans can be customized to your interests, activity levels, and whether you’re traveling with children or only with your beloved.
Visiting Aspen as a Family
For example, families will enjoy the convenience of staying at the St. Regis where the surrounding streets are quiet, the rooms are welcoming, and the pool is heated year-round. Visitors are able to borrow a car to go for family drives. Children will love that turndown service involves candies being left on their pillows and the fact that the St. Regis has a dog in residence, Kitty Astor II, who loves cuddling.
Where to Stay for a Romantic Getaway
Couples who want romance on their itinerary should stay at Hotel Jerome where the Yarrow Spa will make you feel your healthiest, sexiest, and most relaxed. Both on-site restaurants are the perfect places to make sparks fly. The Living Room is more of an après-ski destination, but if you cozy up next to a fireplace with cocktails in hand, the whole rest of the world will disappear. Prospect is known for its loyalty to Aspen’s edible flora and fauna. The only thing you’ll love more than your meal is this quality time with each other.
Aspen for Adventurers
The Little Nell is the place for adventure seekers. The biggest draw of this luxury hotel is the fact that it’s ski-in/ski-out to Aspen Mountain. The ski concierge is well-known for their attention to detail, professionalism, and knowledge about the slope conditions. When you stay here, you can hit the slopes early and feel good about your freshly tuned gear.
Start Planning Your Aspen Adventure Today!
Accommodations are only one part of your Aspen itinerary; ALC will handle your hotel bookings and everything else you need! Our team can curate experiences that will pique your interests and match the intended vibe of your trip, all while your concierge acts as a single-point-of-contact. Contact Aspen Luxury Concierge today to start planning your dream trip!
