Aspen Trip Planner – What You Need to Know Before You Visit

You might not expect for a little mountain town in Colorado to be so well known for luxury travel that it attracts celebrities, billionaires, and CEOs. But that’s just what Aspen does! If you would like to travel the way the rich and famous do, then you’re going to need a professional Aspen trip planner. At Aspen Luxury Concierge (ALC), we’re Aspen’s only private concierge company, crafting unforgettable luxury experiences for travelers who want every detail handled for them, and we’ve put together this guide to help you decide what to do when you use an Aspen trip planner. 

What’s the Best Way to Organize a Trip to Aspen?

The best way to organize a trip to Aspen is to start by deciding what kind of experience you want: an adventure-focused trip (skiing, hiking, biking, rafting) or a lifestyle-focused escape (fine dining, spa, shopping, nightlife). Next, choose your season—winter for skiing, summer for outdoor adventures, fall for leaf-peeping, or spring for a quieter, more private visit—then build your itinerary around those priorities.

If Aspen is in your future, this guide will cover everything you need to know to make your trip perfect. 

Getting to Aspen & Getting Around

The first step to planning any trip is how to get there. Once you’ve gotten that squared away, you should plan how you are going to get around.

Flying Into Aspen

There are 3 ways that visitors get to Aspen:

1. Fly Commercial into Pitkin County Airport – It’s 10 minutes outside Aspen and the most convenient option. 
2. Fly into Denver International Airport then Drive – It’s about a 4 hour drive if done all at once. If you have concerns about altitude sickness, then spending a night in Denver or Golden can help ease you into the Aspen altitude.
3. Fly Private into Pitkin County Airport – This is the most luxurious option! You won’t even have to go through security or wait to disembark.

Getting Around Aspen

Apps like Lyft and Uber aren’t a great way to get around in Aspen, especially in peak season. Instead, most luxury travelers rely on a mix of private drivers, hotel shuttles, and walking.

• Private transportation: For a truly seamless experience, many guests choose private transportation for the duration of their stay. Think chauffeured SUVs, luxury sedans, or sprinter vans waiting for you whenever you’re ready to move—airport transfers, ski drop-offs, dinner reservations, late-night pickups, and everything in between.
• Get a rental car – There is not very much parking downtown and much of it is paid. This option works well for visitors who feel comfortable driving in the snow and don’t mind circling the block to find a spot. 
• Utilize shuttle services and buses – All the luxury hotels have shuttles that take visitors to a few key locations. Aspen also has safe, reliable, and free buses that can take you where you need to go. 
• Walkability – Downtown Aspen is pretty walkable. If you stay at one of the main hotels in the center of the action, you’ll be able to walk to the slopes, restaurants, clubs, and galleries with ease.  

According to an Aspen Trip Planner, When is the Best Time to Visit?

Unlike most travel destinations, there isn’t a bad time of year to come see Aspen. Different seasons bring different activities and different sizes of crowds. 

Here’s a breakdown of what Aspen has to offer throughout the year:

Aspen in Winter

The winter months are ski season! From November to March, the valley receives frequent, fresh snow that transforms the 4 mountains into paradise for skiing, snowboarding, snowmobiling, and snowshoeing. It does get very cold – think lows of 10 degrees and highs of 35 – so visitors need to pack lots of layers and a thick coat. 

This is the busiest time of year. There are frequent events and festivals that attract visitors from all over the world. The main events to schedule your trip around are: 

• Wintersköl – Mid-December
• Aspen Gay Ski Week – Mid-January
• X Games Competitions and Concerts – End of January
• World Cup Skiing – Beginning of January
• Snow League – Late February

Aspen in Summer

Aspen Summer brings with it warmer temperatures and blue skies. The weather plus the abundant natural beauty of the mountains make it the perfect time of year for hiking, biking, fishing, and riding the gondola. The summer is wildflower season, so the trails fill up with visitors who want a glimpse of the lush, colorful fields. 

The most notable events to mark down in your Aspen trip planner are:

• Wildflower season – Starts in late May, peaks in July, and ends in August
• Food and Wine Classic – Mid-June
• Aspen Music Festival – Late-June until mid-August
• JAS Jazz Festival – Labor Day Weekend

Fall in Aspen

The fall season is better known as the “leaf peeping gold rush” season. The trees start to change color in late-August so by September, entire mountainsides are adored in golden leaves. If you visit in October, the colors will have shifted to more orange hues as the leaves begin to fall off the trees. 

Fall is a popular time of year for hiking and photography. There are some crowds, but not nearly as many visitors as Aspen might get in the summer and winter. 

Aspen in Spring

Spring is the shoulder season, so it’s when Aspen is the quietest. There are both upsides and downsides to visiting in the spring. It is the cheapest time to visit because there is no peak season pricing. The town is also quieter, calmer, and offers a more private visiting experience. However, not all restaurants, bars, and clubs are open in the spring. There is also the risk of your hiking plans getting rained out by spring showers that can appear with little warning. 

How Many Days Do You Need in Aspen?

Visitors generally agree that it takes a minimum of 5 days to experience Aspen properly; however, you might opt for a longer or shorter trip depending on your schedule, interests, and what brings you to town. Some families may choose to spend a month in Aspen to celebrate the holidays, while others often spend spring break in the valley to capitalize on the spring skiing and party scene. 

Below are examples of Aspen itineraries that your trip planner may arrange for you. 

Winter Itinerary from ALC’s Aspen Trip Planners

Day 1:

• Arrive in Aspen and get settled
• Lunch at Meat and Cheese, then exploring Aspen and shopping
• Get fitted for rentals (or, if you already own gear, go snowmobiling)
• Drinks at the Jerome Living Room before dinner
• Dinner at Angelo’s

Day 2:

• Ski Aspen Mountain
• Lunch and après at Eleven212
• Ski down and head to après at Snowlodge
• Dinner at Matsuhisa
• After dinner drinks at Hooch

Day 3:

• Ski Aspen Highlands
• Lunch and après at Cloud Nine
• Late dinner at Steak House 316
• Table at Sterling after dinner

Day 4:

• Ski Snowmass
• Lunch at Sam’s
• Drinks at Après Ski Club or Bunny’s Social Club
• Dinner at home with private chef

Day 5

• Breakfast at the hotel
• Fly home

Summer Itinerary from ALC’s Aspen Trip Planners

Day 1:

• Arrive in Aspen and get settled
• Lunch on the patio at Ajax Tavern, then walk around downtown
• Afternoon hike on Smuggler Trail
• Dinner at Cache Cache

Day 2:

• Go to JUS for breakfast then walk through the Saturday Farmer’s Market
• Head up the gondola for mountain top yoga
• Lunch at the Sundeck
• Afternoon horseback ride at T Lazy 7 Ranch
• Dinner at Wayan
• After dinner drinks at Bad Harriett Speakeasy

Day 3:

• Early morning fly fishing trip
• Lunch in town at Clark’s Oyster Bar
• Afternoon massages at the St. Regis Spa
• Dinner at Catch Steak
• Clubbing at Madame Ushi

Day 4:

• Breakfast at The Bear Den or Poppycocks
• Rent E-Bikes and bike to Woody Creek Tavern 
• Late lunch at WCT
• Afternoon on the Roaring Fork River, either rafting or paddleboarding
• Dinner at The Wild Fig

Day 5

• A little morning shopping in town
• Fly home

Where to Stay in Aspen 

When you visit Aspen, you have the choice to stay at a vacation rental or a luxury hotel. There are 3 main luxury hotels in town:

The Little Nell

The most popular is The Little Nell. It is the place to stay for skiers and snowboarders throughout the winter season. The Little Nell provides a bespoke skiing experience through its highly knowledgeable ski concierge as well as the ski-in/ski-out access to Aspen Mountain. After a day on the slopes, you can hit Ajax Tavern for a lively après-ski afternoon. 

St. Regis

The St. Regis is known as the hotel most rich in traditions and personalized service. When you stay here, it feels like you’re stepping back in time. Reviews in Aspen trip planner publications highlight the butler service as one of the selling points of the St. Regis. Guests enjoy personalized service whether it’s in their rooms, at the RAKxa spa or poolside. 

Hotel Jerome

The Hotel Jerome has been a centerpiece of Aspen for over a hundred years. The rooms and building combine Gilded Age luxury with modern comforts. Guests love the coziness provided by fireplaces in key rooms as well as the herbal and botanical healing practices at Yarrow Spa. What makes Hotel Jerome stand out is the curated experiences that are exclusively open to guests. These change by the season, but you can expect brand pop ups, artists and designers in residence, outdoor adventure tours, cultural après events, and live music whenever you visit. 

The Top Things to Do in Aspen, Colorado

What makes Aspen the kind of place that people visit year after year is the sheer variety of things to do. There’s something here for everyone! 

There are 3 main categories of activities that an Aspen trip planner would recommend: 

Outdoor Adventures

• Hiking – The valley is home to hundreds of trails that range from very easy to extremely challenging.
• Biking – The Snowmass Bike Park is a paradise for mountain bikers. For cyclists, there’s the 42-mile Rio Grande Trail. If you visit in the winter, fat tire biking over the snow is all the rage!
• Skiing/Snowboarding – There are 4 resorts in town with all different terrain and types of runs.

Luxury Lifestyle & Culture

• Art museums – The Aspen Art Museum is free to attend!
• Spas – Check out this guide for an overview of what healing practices the locals spas specialize in. 
• Shopping – Downtown has everything from ultra-local handmade specialties to designer storefronts that sell Aspen-specific pieces.
• Luxury Dining – Some of the best chefs in the world run restaurants in town. No matter what you’re craving, you can find it in Aspen!
• Après Ski – The party scene and ski scene go hand to hand. You can spray champagne at Cloud 9 then ski down the mountain and sip cocktails at Hooch.

Unique Experiences

• Palm Tree Music Festival – Takes place the 3rd week of February; the limited number of tickets sold mean that attendees can enjoy and exclusive and intimate music experience.
• Hi-Fi Concert Series – As the days warm up, so do the beats. Snowmass is mid-February. DJs take over Aspen the last weekend in March, just in time for spring break!
• X Games – During the day, the best athletes in the world compete for glory. At night, all of Aspen is invited to party and jam out.
• Snow League – Founded by snowboarder Shaun White, this league places athletes head-to-head in a post-Olympic victory lap. 

Aspen Trip Planner Checklist

• Flights booked
• Accommodation secured
• Ski passes reserved
• Restaurant reservations
• Rental gear
• Travel insurance

If you’re acting as your own Aspen, Colorado trip planner, then that long checklist is all up to you to remember and handle. It doesn’t have to be! Aspen Luxury Concierge is the premier trip planning service in the Roaring Fork Valley. Our team acts as a single point of contact to do all the planning, calling, arranging, confirming, reserving, and remembering for you. 

Frequently Asked Questions

Here are some frequently asked questions to help you plan your perfect Aspen getaway:

When it comes to billionaires staying in Aspen, they typically opt for ultra-luxurious, private accommodations. Many choose The Little Nell, Aspen’s most exclusive hotel, offering ski-in/ski-out access, private ski concierges, and high-end dining. Others rent luxury chalets or mansions in private neighborhoods like Red Mountain, known for its stunning views and secluded atmosphere. Aspen Luxury Concierge (ALC) often arranges stays in exclusive private estates that offer unmatched luxury, comfort, and privacy, ensuring a VIP experience from start to finish.

Plan Your Trip with ALC!

Here’s how it works: If you know what you want to do, you tell us and we take care of it for you. If you would like some recommendations from locals, our team will build you a customized itinerary that is tailored to your interests and designed to give you an incredible experience!

More than that, ALC has connections that we can leverage to secure you the VIP treatment that celebrities get when they visit. Let’s say that you heard about Caribou Club – the private, members-only establishment – and want to attend an event there. Done. ALC can make it happen!

Are you ready to experience all the natural beauty and culture of Aspen? Get in touch with Aspen Luxury Concierge to start planning your adventure!