From first tracks to fireside dinners, Aspen delivers a winter escape where alpine adventure meets effortless luxury. This three-day itinerary captures the best of ski culture, après-ski glamour, and off-mountain experiences—without feeling rushed.

Day 1: Arrival, Aspen Mountain & Après in Town

Morning | Arrive & Settle In
Fly into Aspen–Pitkin County Airport and check into your hotel. Whether you choose a ski-in/ski-out resort or a boutique lodge in town, drop your bags and change into your mountain layers—Aspen starts strong.

Late Morning | Ski Aspen Mountain (Ajax)
Head straight to Aspen Mountain, known for its steep terrain and unbeatable views over town. Advanced skiers will love the groomers and challenging runs, while intermediates can cruise the upper mountain before lunch.

Lunch | On-Mountain Dining
Reserve a table at Sundeck or Bonnie’s for alpine comfort food and panoramic views—think schnitzel, truffle fries, and warming cocktails.

Afternoon | Leisure Ski or Village Stroll
Ski a few more runs or descend early to wander through downtown Aspen’s art galleries, bookstores, and heritage buildings.

Après-Ski | Iconic Aspen Scene
Kick off the evening at Ajax Tavern, a legendary après spot for rosé, truffle fries, and people-watching. As the sun dips behind the peaks, the patio buzzes with energy.

Dinner | Elevated Comfort
Book dinner at Matsuhisa Aspen for inventive Japanese cuisine or Cache Cache for classic French dishes in an intimate setting.

Day 2: Snowmass Adventure & Fireside Evening

Morning | Breakfast in Town
Start the day with locally roasted coffee and pastries at Spring Café, beloved by locals.

Midday | Ski Snowmass
Spend the day at Snowmass, Aspen’s largest and most diverse mountain. With wide-open groomers, glades, and beginner-friendly zones, it’s ideal for full-day exploration.

Lunch | Mountain Views
Stop at Elk Camp or The Cabin for a refined on-mountain lunch featuring seasonal ingredients and sweeping views.

Afternoon | Spa or Scenic Pause
Return to your hotel for a spa treatment, or unwind in a heated outdoor pool with mountain backdrops.

Evening | Fireside Dining
Dine at Element 47 for refined mountain cuisine or White House Tavern for elevated comfort food in a cozy, candlelit setting.

Night | Winter Calm
End the night with a stroll through snow-dusted streets or a nightcap by the fire—Aspen evenings feel magical under fresh snowfall.

Day 3: Culture, Relaxation & a Scenic Farewell

Morning | Leisurely Start
Enjoy breakfast at your hotel or revisit a favorite café. Take the morning slow—this is Aspen at its most serene.

Late Morning | Aspen Art Museum or Shopping
Explore the Aspen Art Museum for contemporary exhibitions, or browse designer boutiques and local shops along Galena Street.

Midday | Snowshoe or Sleigh Ride
Try a guided snowshoeing tour through nearby trails or book a horse-drawn sleigh ride for a classic winter experience.

Lunch | Casual & Chic
Grab lunch at Meat & Cheese Restaurant and Farm Shop or Big Wrap for a relaxed but flavorful sendoff.

Afternoon | Departure
Head to the airport or begin the scenic drive out of town, with snow-covered peaks marking the perfect end to your Aspen escape.

❄️ Insider Tips for Aspen in Winter

• Book dinner reservations early, especially during peak ski season and holidays
• Ski Aspen Mountain early to avoid lift lines
• Layer smartly—temperatures change quickly between slopes and town
• Midweek stays offer fewer crowds and better availability

❄️ Bozeman vs. Aspen: Two Winter Escapes, Two Very Different Vibes
Here’s how to choose the winter escape that fits your travel style.

Discover the quiet beauty and dramatic contrast of Tahoe in its most photogenic season in ❄️ Why Winter Is the Best Time to Photograph Lake Tahoe. Read on to plan your winter shoot and capture snow-dusted peaks, icy blues, and serene landscapes at their most magical.