usa · December — March · July (Music Festival)
The Little Nell at four. Casa Tua under the lights. Cloud Nine for the chukkers in the snow. Aspen is the winter equivalent of the Hamptons — the same families, the same hosts, three thousand metres higher. The summer Aspen, quieter and arguably better, is the secret.
Hotels
Book the room — handled personally.
Five-Star · 5★Aspen's only Five-Star, Five-Diamond, ski-in/ski-out hotel — 92 rooms at the base of the gondola, opened 1989.
Historic · 5★The 1889 silver-mining-era landmark on Main Street, run by Auberge, with the J-Bar that has been the town's living room for a hundred and thirty-five years.
5★ ResortThe 179-room St. Regis at the base of Aspen Mountain, the most reliably American five-star in town.
Design · 4★The 88-room W on Wagner Park, with the rooftop pool that is the town's loudest après-ski deck.
Festive · clubs, line-ups, long lunches
Reserve the table for the night out — handled personally.
Italian · MembersThe Aspen outpost of the Miami private club — fine Italian, members' room downstairs, the festive dining room in town.
On-mountain · Aspen HighlandsThe mid-mountain alpine cabin on Aspen Highlands — fondue and raclette for lunch, champagne-spraying dance party at two o'clock.
Japanese · NobuThe 1998 Aspen Nobu — the first Matsuhisa outside Beverly Hills, in a Victorian house on Main Street, and still the festive dinner of every ski week.
Authentic · the quiet rooms
Reserve the quiet dinner — handled personally.
Contemporary · Michelin GuideThe Little Nell's flagship dining room — Michelin Guide-recommended Colorado contemporary, and the most serious wine cellar in the Rockies.
Slope-side · Aspen MountainThe 1960s cabin off Tourtelotte Park — the slope-side lunch that has fed Aspen Mountain for sixty years.
Italian · 1994The 1994 Italian on Mill Street — voted Aspen Times Best Italian 2025 and 2026, and the regulars' table for thirty winters.
Sport · tennis, padel, polo, golf
Book the court · the green · the chukkers — handled personally.
Ski school · PrivateThe Aspen Snowmass Ski & Snowboard School private instructors — priority lift access, four mountains, one card.
Public · 18 holesThe Frank Hummel championship course two miles from town — ranked among Golfweek's 50 best municipal courses in America.
Private aviation · jets
Charter a jet · point to point — handled personally.
Mountain · Sardy FieldThe 8,000-foot strip at 7,838 feet elevation — the only sensible way into Aspen in a winter storm.