Our Aspen WINTER ITINERARIES
Aspen Winter Itinerary
A Week of Elevated Adventure
DAY 1 | ARRIVAL
Upon arrival in Aspen, our private shuttle will meet you at the airport and transport you to the luxurious St. Regis Resort (or your pre-arranged accommodations). After settling in, we’ll kick off the week with a warm welcome dinner at the iconic Pine Creek Cookhouse.
DAY 2 | WORLD CLASS RESORT SKIING
Spend the day skiing or snowboarding at one of Aspen’s legendary ski resorts. With perfectly groomed runs and incredible terrain, there's something for every level. Evening at your leisure—relax, explore town, or enjoy a dinner of your choosing.
DAY 3 | LIFT-ASSISTED BACKCOUNTRY SKIING
Experience the solitude and fresh powder of Colorado’s backcountry with the convenience of lift access. The Elk Mountains offer jaw-dropping bowls and hidden lines just a short trek from the resort lifts.
DAY 4 | BACKCOUNTRY SNOWMOBILING
Today we trade skis for horsepower as we explore the vast terrain of the Grand Mesa by snowmobile. We'll break for lunch at a remote backcountry lodge, then head back and wind down with dinner at Allegria in Carbondale.
DAY 5 | RESORT SKIING + HOT SPRINGS RECOVERY
Return to the slopes for another epic day at the resort, then recover in style. Soak in nearby hot springs, enjoy a private yoga session, and indulge in a massage. Dinner this evening is at Izakaya in Carbondale.
DAY 6 | SAN JUAN HELI-SKIING
The crown jewel of your winter adventure—heli-skiing in the San Juans. Drop into 10,000 to 14,000 vertical feet of untouched powder with just you and your crew. This is Colorado skiing at its absolute peak.
DAY 7 | CAT SKIING + FAREWELL DINNER
Cap off the trip with a full day of cat skiing in the powder-filled terrain off the backside of Aspen Mountain. That evening, we’ll gather for a special farewell dinner in town to toast an unforgettable week.
DAY 8 | DEPARTURE DAY
After breakfast and final farewells, private shuttles will transfer you to the airport for your departure.
Aspen Winter Weekend Itinerary
4 Days of Indulgence & Adventure
Day 1 | Arrival & Alpine Welcome
Morning: Arrive in Aspen and private transfer to your luxury accommodations (The Little Nell, Hotel Jerome, The St. Regis Aspen, or W Aspen). Settle in with welcome drinks and sweeping mountain views.
Afternoon: Unwind, explore town, or enjoy the rooftop Wet Deck at the W with mountain fire pits and après-ski energy.
Evening: Dinner at Matsuhisa Aspen or Kenichi, both Aspen staples for upscale Japanese cuisine and elevated atmosphere. Optional moonlight stroll through Aspen’s lantern-lit streets.
Day 2 | Slopes & Spa Bliss
Morning: Ski Aspen Snowmass – Choose from Ajax for in-town access and steeps or Snowmass for long, flowing terrain. Upgrade to a private ski guide or instructor for a seamless experience.
Afternoon: Champagne-fueled après-ski at Cloud Nine or Ajax Tavern. Relax with a signature massage, oxygen therapy, or CBD recovery ritual at St. Regis Remède Spa.
Evening: Dinner at a cozy local ramen spot—perfect comfort food after a big mountain day. Fireside relaxation or optional live music at Belly Up.
Day 3 | Sky, Speed & Serenity
Morning: Helicopter Flightseeing Tour – Take to the skies for jaw-dropping views of Maroon Bells, Pyramid Peak, and the Elk Mountains.
Afternoon: Snowmobiling Adventure through White River National Forest or up to the ghost town of Independence Pass. Then unwind in nature with a Hot Springs Yoga Experience—flow through a private or small-group session while soaking in mineral-rich geothermal waters, surrounded by snow-capped serenity.
Evening: Horse-Drawn Sleigh Ride & Dinner – Glide through snowy meadows to a tucked-away mountain cabin for an intimate alpine feast.
Day 4 | Leisure & Departure
Morning: Enjoy a relaxed breakfast at your hotel. Stroll and shop along Galena Street—Aspen’s luxury shopping district featuring Kith, Gorsuch, Ralph Lauren, and more.
Afternoon: Private transfer to the airport or onward travel via charter.
