Aspen, Colorado, is the ultimate winter wonderland, offering world-class skiing, breathtaking mountain scenery, and a vibrant après-ski culture. Whether you’re here for adventure, luxury, or a bit of both, five days in Aspen is the perfect amount of time to experience its magic.
Since most visitors come for a short but action-packed trip, we’ve put together this 5-day Aspen itinerary to help you make the most of your time. You’ll find a blend of outdoor adventures, must-visit restaurants, cozy accommodations, and insider tips to ensure an unforgettable trip.
While it’s impossible to experience everything Aspen has to offer in just five days, this guide will take you through the best ski slopes, scenic hikes, indulgent dining spots, and unique local experiences to give you a well-rounded taste of this iconic mountain town. Get ready to explore Aspen in style!
5 Day Aspen Itinerary Overview
Here’s a quick overview of your 5 day Aspen, Colorado itinerary, complete with booking links to streamline your travel planning. While you don’t have to do every activity, pick the ones that excite you the most! To ensure a smooth trip, we recommend booking your accommodations, rental car and must-do experiences in advance to secure your spot.
- Day 1: Arrival & Downtown Aspen Exploration
- Pick up rental car
- Check in to hotel
- Explore downtown Aspen
- Day 2: Skiing at Aspen Mountain
- Full-day Skiing or Snowboarding at Aspen Mountain (Ajax)
- Ice Skating at CP Burger Rink
- Day 3: Adventure & Relaxation
- Snowmobiling Tour
- Spa Day at Remede Spa
- Day 4: Ski Snowmass & Scenic Exploration
- Ski or Snowboard at Snowmass Mountain
- Snowshoeing at Ashcroft Ghost Town
- Day 5: Scenic Beauty & Departure
- Take a final stroll through Aspen’s many hiking trails
- Depart for airport
Detailed 5 Day Aspen Itinerary
Overview of the Area
Nestled in the heart of the Rocky Mountains, Aspen, Colorado, is a premier year-round travel destination, best known for its world-class skiing, breathtaking alpine scenery, and upscale mountain charm. Whether you’re carving through powdery slopes at Aspen Snowmass, indulging in luxury après-ski experiences, or exploring the quaint downtown lined with high-end boutiques and gourmet restaurants, Aspen offers a perfect blend of adventure and relaxation.
Beyond skiing, visitors can enjoy snowshoeing, scenic gondola rides, dog sledding, and vibrant cultural attractions like the Aspen Art Museum and historic Wheeler Opera House. In the warmer months, the mountains transform into a paradise for hiking, mountain biking, and fly fishing. With its luxurious resorts, top-rated dining, and stunning mountain views, Aspen is the ultimate destination for travelers seeking both outdoor thrills and refined comfort.
From adrenaline-packed winter sports to cozy fireside retreats, Aspen is a must-visit for skiers, nature lovers, and luxury travelers alike. Plan your perfect Aspen getaway and experience the magic of this iconic mountain town!
Where to Stay in Aspen
- Luxury: The Little Nell
- Boutique: The Hotel Jerome
- Budget: Creekside Suites
Day 1
Check-in at Hotel (Choose based on preference)
Morning:
- Breakfast at Paradise Bakery & Café
- Explore Downtown Aspen – Stroll through Hyman Avenue Mall, visit Aspen Art Museum, and browse local boutiques.
Afternoon:
- Lunch at Ajax Tavern – Try their famous wagyu burger & truffle fries.
- Ride the Silver Queen Gondola for breathtaking mountaintop views.
Evening:
- Dinner at Matsuhisa Aspen – High-end Japanese fusion cuisine by Nobu Matsuhisa.
- Nightcap at The W Aspen Rooftop – Panoramic mountain views with signature cocktails.
Day 2: Skiing at Aspen Mountain & Après-Ski Fun
Morning:
- Breakfast at Poppycock’s Café – Famous for oatmeal pancakes.
- Full-day Skiing or Snowboarding at Aspen Mountain (Ajax)
Afternoon:
- Lunch at Element 47 – Fine dining inside The Little Nell.
- Après-Ski at Chair 9 – One of Aspen’s best après-ski bars with live music.
Evening:
- Dinner at Steakhouse No. 316 – Classic steakhouse with elegant ambiance.
- Ice Skating at CP Burger Rink followed by spiked hot chocolate by the fire pits.
Day 3: Adventure & Relaxation
Morning:
- Breakfast at Jour de Fête – Cozy French café with pastries & burritos.
- Snowmobiling Tour with T-Lazy-7 Ranch – Ride through Maroon Bells wilderness.
Afternoon:
- Lunch at Meat & Cheese Restaurant – Farm-to-table dining with charcuterie boards.
- Spa Day at Remède Spa (St. Regis Aspen) – Luxurious facials, massages & heated pools.
Evening:
- Casual Dinner at White House Tavern – Laid-back, gastropub-style dining.
- Live Music at Belly Up Aspen – Catch a concert at Aspen’s top music venue.
Day 4: Ski Snowmass & Scenic Exploration
Morning:
- Breakfast at The Crepe Shack – Sweet & savory crepes.
- Ski or Snowboard at Snowmass Mountain – Largest ski area with varied terrain.
Afternoon:
- Lunch at Lynn Britt Cabin – Ski-in/ski-out cabin dining in the mountains.
- Snowshoeing at Ashcroft Ghost Town – Explore historic ghost town trails.
Evening:
- Dinner at Betula Aspen – Chic, French-Latin cuisine with mountain views.
- Nightcap at Hooch Craft Cocktail Bar – Cozy cocktail bar for post-dinner drinks.
Day 5: Scenic Beauty & Departure
Morning:
- Breakfast at Local Coffee House – Grab a latte & quick bite.
- Dog Sledding with Krabloonik – Thrilling dog sled ride through Aspen’s backcountry.
Afternoon:
- Lunch at The Wild Fig – Mediterranean-inspired bistro.
- Final stroll through Aspen’s scenic trails before departure.
Afternoon Departure
- Drive to Aspen/Pitkin County Airport (ASE)
Final Thoughts
This 5-day Aspen itinerary blends adventure, luxury, and relaxation, ensuring an unforgettable Rocky Mountain getaway. Whether you’re skiing world-class slopes, enjoying après-ski cocktails, or exploring Aspen’s backcountry, this itinerary will help you make the most of your trip.
Which Aspen experience are you most excited for? Let me know in the comments!
