The Perfect Plan for an Adventure-Loaded and Relaxing Vacation in Aspen

Welcome to the ultimate Aspen summer itinerary! If you’re looking for a vacation filled with adventure and relaxation in the stunning surroundings of Aspen, then this is the plan for you. From breathtaking hikes and scenic bike rides to indulgent dining and spa experiences, we’ve curated a five-day itinerary that combines local knowledge of Aspen’s outdoor beauty and its luxury offerings. 

Arrival: Enter Aspen Vacation Mode! 

Arrive in Aspen and check in to your luxury vacation home. Relax by the hot tub or with a glass of wine on your outdoor patio in the evening sun. 

Aspen Snowmass Luxury Vacation Rental Summer


Day One: Rewarding Hikes and Sweet Treats

Start your day with coffee and breakfast at Jour De Fête cafe before heading out on a hike up ‘Ute Trail.’ This steep but rewarding hike leads to some of the most spectacular views Aspen offers. After about 30 minutes of incline hiking, you will reach the peak with 360° views over Downtown Aspen and its surrounding mountains. Ensure you bring lots of water to combat Aspen’s high altitude! 

For lunch with a beautiful view, visit Ajax Tavern at the base of Aspen Mountain. With a large summer patio, enjoy a well-deserved wagyu cheeseburger and truffle fries after your morning hike. Then, for a sweet treat, walk to Paradise Bakery, Aspen’s renowned ice cream shop.

Return to your vacation rental to relax and reset before some late afternoon shopping around town. For a unique Aspen experience, visit Kemo Sabe or one of our many art galleries in town!

This evening, dine at one of Aspen’s many delectable restaurants. For outdoor dining, we recommend Betula, Campo, Cache Cache, the French Alpine Bistro, or Matsuhisa. These restaurants will book up, so ensure you reserve before arrival! For more options, view our restaurant guide.

Downtown Aspen Summer


Day Two: Farmer’s Market and an Exceptional Aspen Dinner

Enjoy a leisurely Saturday morning at the Aspen Farmer’s Market. Occupying Downtown Aspen from 8:30 am-2 pm every Saturday, walk through local food and art vendors with a stunning backdrop. Then, stroll through the stalls with a coffee and fresh croissant from one of our local bakeries! 

For a mountain experience like no other, rent E-bikes this afternoon and head to the Maroon Bells wilderness area. Pack a lunch from Big Wrap, a local’s favorite takeout spot for healthy wraps and salads. 

This evening, venture out to Pine Creek Cookhouse in Ashcroft Valley, a 30-minute drive from Downtown Aspen. This mountain-chalet restaurant is a quintessential Aspen summer experience. Choose to drive, hike, or horseback ride through the wildflowers ending with a rustic alpine-cuisine dinner. Then, view the sunset over the Elk Mountains as you dine in one of the most picturesque restaurants Aspen offers!

Maroon Bells Biker in Summer


Day Three: Paddle Through Nature and a Bluegrass Afternoon

This morning, take a stroll in Downtown Aspen to Unravel Coffee for breakfast. We recommend walking through the pedestrian mall between Cooper and Hyman Ave for beautiful aspen-tree-lined streets and mountain views. 

After breakfast, rent stand-up paddleboards and explore the North Star Preserve 5 minutes East of Aspen. Then, book a guided tour or rental-only and enjoy the calm Roaring Fork River water with stunning scenery. We recommend Elk Mountain Expeditions for your rentals. 

For lunch with great entertainment, venture up the Aspen Mountain Gondola for ‘Bluegrass Sundays.’ Enjoy live bluegrass bands with a beautiful mountain backdrop from 12-3 pm at the Sundeck Restaurant.  

Let one of our highly experienced private chefs curate dinner at your vacation rental this evening. From 5-course plated meals to family-style feasts, our recommended chefs can elevate any dinner experience right in the comfort of your vacation home. 

Aspen Mountain View in Summer


Day Four: Sunrise Hikes, Spa Afternoons, and Local Treasures

Rise and shine this Monday morning with a hike up Smuggler Mountain Road. This 2.9-mile hike boasts stunning views over Aspen Mountain once you reach the top. 

After your morning workout, enjoy lunch at the White House Tavern on ‘restaurant row’ aka E Hopkins Ave in Downtown Aspen. They serve a simple menu of sandwiches, salads, and sides in a lively atmosphere. We highly recommend the ‘Crispy Chicken Sandwich’ and ‘Smoked Trout Dip.’ 

Enjoy a spa afternoon at the St Regis Aspen’s spa for a break from outdoor adventures. Relax with a spa treatment at one of the world’s best-known hotel spas, followed by the oxygen lounge, cold plunge and jacuzzi room. After rest and rejuvenation, complete your afternoon with retail therapy throughout downtown Aspen’s numerous luxury stores!

Drive down to a Roaring Fork Valley classic, Woody Creek Tavern, this evening. Locals and visitors alike enjoy the tavern’s rustic, friendly atmosphere, with indoor and outdoor seating and over 40 years of memorabilia décor. 


Remede Spa, St Regis Aspen

Photo Courtesy of: St Regis Aspen


Day Five: Pick-An-Adventure Day

Pick an adventure for the last day on your ultimate Aspen summer itinerary! From wilderness Jeep tours, fly fishing experiences, or white-water rafting journeys, let our concierge book you a day of adventure. With lunch included in most activities, pack sunscreen and a camera for views of a lifetime! See our comprehensive concierge options here: 

For your last Aspen dinner, visit the beautiful Hotel Jerome’s garden patio with a delicious selection of garden-to-table menu items and seasonal cocktails in an idyllic garden setting.

Aspen Summer Jeep Tour

Photo Courtesy of: Blazing Adventures


Departure: Bid Farewell to Aspen with Lasting Memories!

We hope your summer vacation in Aspen has brought your life-long memories, culinary delights, and lots of exploring nature in the sunshine! For more ideas on summer activities in Aspen, visit our blog post: “15 of the Best Things to Do in Aspen in the Summer”.



Is Aspen worth visiting in the summer?

Absolutely, yes! There is a common saying that you come to Aspen for the winter and stay for the summer. There are just as many wonderful things to do and see in the summer in Aspen. From June to October, tourists visit Aspen Snowmass for the incredible wilderness, shopping, dining, and numerous festivals and events.

What is the weather like in Aspen in the summer?

Summer in Aspen is mild and pleasant! Daytime temperatures range from the 70s to 80s Fahrenheit (20s to 30s Celsius), while evenings can be cooler, typically dropping into the 40s to 50s Fahrenheit (5 to 15 degrees Celsius). It’s always a good idea to bring layers and a rain jacket for any weather changes.

What activities are popular during the Aspen summers?

Aspen offers a wide-range of indoor or outdoor activities in the summer months. Some popular options include hiking, mountain biking, E-biking, fly fishing, golfing, horseback riding, river rafting, stand-up paddleboarding, art museums, shopping, culinary adventures, and enjoying concerts and festivals.

Are there any festivals or events in Aspen during summer?

Aspen plays host to many world-renowned festivals during the summer. Some notable events include the annual Food & Wine Classic, the Aspen Ideas Festival, the Aspen Musical Festival and School, Jazz Aspen Snowmass, and the Snowmass Balloon Festival. For more ideas on the ultimate Aspen summer itinerary, see our Aspen Summer Events Calendar.