Aspen in Winter: A Luxury Gay Ski Escape

Your ski guide meets you after breakfast. Starting on Aspen Mountain directly from the hotel, they will spend time understanding how you ski and what you want from the week before taking you through the terrain that suits you best. Wide groomed cruisers on the Ruthie’s area if you want to ease in, the steeper pitches of Bell Mountain if you want to be pushed.

Lunch at Bonnie’s, perched at 11,000 feet with views that justify the trip on their own. Après at the Hotel Jerome’s J-Bar, one of the great end-of-ski-day institutions in American mountain towns.

A short shuttle to Snowmass, the largest of the four Aspen Snowmass mountains and the one that rewards unhurried exploration. The terrain is more varied and the crowds thinner than Aspen Mountain.

Half day on the slopes, then back to town for an afternoon at the St. Regis spa, which is excellent and worth building into any winter itinerary here. Consider having dinner at Matsuhisa, Nobu’s Aspen outpost, which has been an institution on the Aspen restaurant circuit for years.

A slower morning by design. A private guided snowshoe excursion takes you out to the Maroon Bells, the twin fourteeners just outside town that look, in winter, like a landscape from another century. The road is closed to vehicles in the colder months, which means you have the terrain largely to yourself.

The Cloud Nine Snowcat Dinner is the ultimate alpine indulgence, offering an exclusive journey to the summit of Aspen Highlands. Your evening begins with a thrilling ascent in a custom, open-air luxury snowcat, climbing to 10,740 feet where the jagged, moonlit peaks of the Maroon Bells create a cinematic backdrop. Inside the warm, glowy embrace of the bistro, you are treated to a sophisticated four-course feast of Swiss-Alpine cuisine, including bubbling raclette, decadent fondue, and world-class wine pairings.

Aspen Highlands is where the serious skiers tend to disappear. The Highland Bowl, reached by a 30-minute boot-pack hike from the top of the lift, is one of the most rewarding ski experiences in North America when conditions cooperate.

Your guide will read the snowpack and advise. Cloud Nine Alpine Bistro on the mountain does a famously celebratory lunch. A quieter evening: the Caribou Club for dinner if you have the connection, or the Little Nell’s bar for a nightcap close to home.

A day without skis. Aspen’s cultural infrastructure is easy to underestimate from the outside. The Aspen Art Museum is a serious institution in a Shigeru Ban building that rewards a couple of hours.

Wheeler Opera House has a winter programme worth checking in advance. Browse the galleries on Galena Street, have a long lunch at Casa Tua, and spend the afternoon however the week has not yet allowed. A massage at the Little Nell spa if the legs need it. Dinner at Betula, which represents some of the most considered cooking in town.

A morning at Buttermilk, which gets unfairly overlooked by the Highlands crowd. The terrain is gentler but the mountain has a charm of its own, and it tends to be quieter than the others.

Back in town by early afternoon for final shopping and a walk through the town while you still have time to appreciate it. The farewell dinner is at your discretion: Element 47 again if the first night merited a return, or something more casual at White House Tavern.

Private transfer to Aspen/Pitkin or onward to Denver.