With four majestic peaks and an abundance of opulent hotels, restaurants, and bars, the picturesque Colorado ski town attracts the world’s most luxurious people Aspen has come a long way since its origins as a silver boomtown in the late 19th century. Although the three-and-a-halfsquare-mile city has a year-round population of less than 7,000 residents, that number balloons to over 25,000 during the high season, from December to March, when it becomes a playground for the ultra-wealthy and the celebrity set. Home to four mountains for skiing and snowboarding—Aspen (or Ajax), Aspen Highlands, Buttermilk, and Snowmass—each with its own unique terrain, Aspen is perhaps best known for its luxurious amenities and après-ski options.
The Little Nell is Aspen’s sole hotel to attain the coveted AAA Five Diamond award. Executive chef Matt Zurod oversees the property’s two restaurants, and the top-tier beverage program has won Wine Spectator’s Grand Award every year since 1997. Guest rooms average 600 square feet, while suites feature Holly Hunt custom furnishings and fireplaces. Listed in the National Register of Historic Places, the elegant Hotel Jerome sits at the foot of Aspen Mountain. Back in the day, Gary Cooper and John Wayne drank at the Jerome; more recent guests have included Bill Murray and Jack Nicholson. Soothe tired muscles in the Jerome’s world-class spa, which uses local minerals in many of its treatments. The hotel has partnered with Mercedes-Benz USA to offer guests “one-ofa-kind drive experiences” during their stay. If it’s old-world luxury you’re looking for, the St. Regis Aspen Resort practically drips with it. The property boasts 179 apartment-style digs, which feature kitchens and, in select rooms, fireplaces, and a team of private butlers is on call to guests staying in suites.
In 1999, Dean Weiler put down stakes in Aspen, where he now runs Dean’s Original Aspen Walking Tours. Unlike, say, Vail, which was created from scratch as a winter resort in 1966 by the late Aspen ski instructor Pete Seibert—a WWII vet who fell in love with the place when he trained there—and uranium prospector Earl Eaton, Aspen has long had its own rich history and infrastructure, which Weiler says gives it “a vibrancy you don’t necessarily have in other places.”
There is “beauty all around us” in Aspen, Weiler says. But there are plenty of wondrous things to do and see indoors, too—like sampling the 200 craft beers and ciders on offer at HOPS Culture. Grey Lady is the place to go for an authentic New England–style lobster roll, and the Caribou Club is one of Aspen’s most exclusive members-only hangouts. The down-to earth vibe brings locals and visitors alike to Justice Snow’s.
When the sun heads below the horizon, the fabulous head to Escobar. Black-and-white photographs of Colombian drug kingpin Pablo Escobar himself “keep measured watch all over—pleased, maybe, with the evidence of a modern, cool crowd claiming their right to feel gratifyingly alive,” the club’s website explains. Table reservations are available (and recommended); minimums vary based on the season and day of the week. Bootsy Bellows is a luxe outpost of the famed Los Angeles nightspot of the same name, and Casa Tua brings the flavors of Northern Italy to the Rockies.
Jimmy Yeager has been supplying Aspen with a good time since 1997. That’s when Yeager opened Jimmy’s, his eponymous bar, restaurant, and area institution. Located at the foot of Aspen (Ajax) Mountain, Jimmy’s is one of the best-known ski spots in the area. There’s no better place for top-end wines, especially since the arrival of certified sommelier Greg Van Wagner in 2014. The focus is on American wines, and the cellar holds more than 650 perfectly kept bottles. A bottle of 2009 Domaine de la Romanée-Conti can be had at Jimmy’s for $1,566.
Yeager’s latest venture is called Jimmy’s Bodega. The ceviche is a must-try, says Weiler, as are the other coastal Mexican dishes in which the Bodega specializes. Other hot spots on Weiler’s must-visit list: the Living Room at Hotel Jerome, for plush couches, a roaring fireplace, and live music. Nearby you’ll find the Ajax Tavern at Little Nell and Shlomo’s Deli & Grill, a new restaurant opened by a local.
One thing Aspen doesn’t want for is variety. For live music, Weiler recommends Belly Up, and steers visitors to the 1880s-era Wheeler Opera House for “all sorts of unique programming.” Hunter S. Thompson fans will definitely want to check out J-Bar at Hotel Jerome, which Thompson used as a campaign headquarters when he ran for county sheriff in 1970. Foodies shouldn’t miss the Chefs Club, and some of the finest Japanese food in the world is found at Matsuhisa, the Aspen satellite of Nobu Masuhisa’s growing sushi den dynasty. The Pine Creek Cookhouse is a destination unreachable by car; winter guests can cross-country ski or snowshoe in. If you’re knackered from a day on the slopes, you can take a horse-drawn sleigh to the front door.
To explore the mesmerizing scenery outside Aspen, start at Go Rentals, which will set you up with a Bentley, Tesla, Porsche, Audi, Land Rover, or Mercedes-Benz during your stay. Rates range from $79 to $1,500 a day. Motion Rent-a-Car will put you behind the wheel of a Mercedes-Benz E300 for $169 and up a day; a Porsche Cayenne for $199 and up a day; or a Bentley Continental Flying Spur from $299 and up a day. If you’re looking for something even more exotic, rent a Lamborghini Huracán from Mile High Drives for $1,199 and up a day (100 miles are included in each 24- hour period; each additional mile $4.49).