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5 Days in Aspen A Wintry Family Adventure

Forge Treasured Memories in Old Aspen

Make unforgettable memories with your family this winter atop the Rocky peaks. Share stories and laughter while cruising ski lifts, then delight in s'mores and hot drinks around a cozy fire during après-ski festivities to create an exclusive alpine adventure for everyone.

Day 1 | Thursday

Mid-Day Arrival

3PM | Ski Fitting

Our fitting outlets have everything you need to get out on the mountain in style. Let our Ski Butlers accommodate you in the comfort of your room, stop by Wild Willow for a fitting (and maybe some extra ski accessories) or schedule an appointment with Four Mountain Sports with our concierge team. After you select the gear that is just right, we will assist with storage.

4PM | Discover Downtown Aspen

Let winter magic take you away one block into the heart of downtown Aspen. Stroll the charming streets and explore restaurants, boutiques and quaint yet exquisite stores that make this town so special.

6PM | Dinner at J Bar

Enjoy a leisure dinner at our iconic, historical J Bar. With its lively buzz and Old West vibe, this 19th century bar remains the town’s social hub, where you can enjoy vintage-inspired beverages and Aspen’s best burger.

Day 2 | Friday

8AM | Breakfast at Prospect

Rise and shine to an unbeatable morning meal at Prospect. With nourishing eats that'll fuel you up for a snow-filled day of adventure, our elevated spot serves memorable meals with approachable flair.

9AM | Hit the Slopes at Buttermilk

Our dedicated bellman will spirit you away to Buttermilk Mountain, where a private instructor awaits with ski lessons and an exclusive guided tour of the majestic snowy peak.

12PM | Lunch at Elk Mountain

Take a well-deserved respite from skiing to indulge in a gourmet lunch and breathtaking scenic views at Elk Mountain.

4PM | Après Ski with Drinks & S’mores

Cozy up to the warmth of an inviting fireplace in our garden, where you can relax on heated outdoor furniture and enjoy après ski with delicious s'mores.

6PM | Dinner in Town

Our experienced concierge team is delighted to provide the ultimate dining experience by recommending one of Aspen's renowned restaurants and effortlessly securing your reservation.

Day 3 | Saturday

8AM | Breakfast at Felix Roasting Co.

Discover an array of delicious pastries, speciality drinks and coffee for a morning delight at the dynamic space of Felix.

9AM | Hit The Slopes at Snowmass

Ride with our cowboy drivers to Snowmass to meet your private instructor for a half-day lesson on the mountain.

12PM | Lunch at Elk Mountain

Take a well-deserved respite from skiing to indulge in a gourmet lunch and breathtaking scenic views at Elk Mountain.

1PM | Explore Snowmass Village

Spend the afternoon in Snowmass Village as you explore its iconic streets and discover thrilling rides on the Alpine coaster and snow tubes.

4PM | Après Ski with Drinks & Snowmen

Come back to an après ski evening spent building your own Frosty the Snowman with our unique snowman kits.

6PM | Dinner in Town

Indulge in another exquisite culinary experience in the heart of Aspen.

8PM | Experience A Historical Horse-Drawn Carriage Tour Ride

Take a private horse-drawn carriage ride through the streets of downtown Aspen and learn little-known facts about historical buildings, sites and epic characters that have called Aspen home.

Day 4 | Sunday

8AM | In-room Dining

Start your morning off leisurely in the comfort of your room with our intimate in-room dining.

10AM | Tour the Maroon Bells

Experience the winter wonderland of the Rockies with our personalized snowmobile tour of the iconic Maroon Bells.

12:30PM | Lunch on Aspen Mountain

Take a journey on the Gondola to discover a delicious lunch on the sundeck, overlooking the stunning Aspen Mountain.

2PM | Explore the Rockies

Enjoy the scenery after lunch or explore the peaks of Aspen Mountain with an adventurous snowshoe tour with ACES.

6PM | Ride a Snowcat to Dinner

Try a new way of transportation by taking a snowcat to Lynn Britt Cabin for a Colorado themed gourmet dinner.

Day 5 | Monday

8AM | Breakfast at Prospect

For your last morning, enjoy another delicious meal at Prospect with nourishing eats to ensure a satisfied journey back home.

10AM | Check Out

Other Sample Itineraries

For Assistance

For availability and logistics, please contact us.

970.920.1000 Plan Your Stay