The Ultimate 4-Night Winter Luxury Aspen Itinerary

Arrive at the Aspen Airport, where your private transfer will whisk you directly to the legendary Little Nell Hotel. This iconic ski-in, ski-out property offers five-star service and unparalleled access to Aspen Mountain. After settling into your room, take the afternoon to wander through town, exploring its charming boutiques and high-end shops.

Be sure to stop at Kemo Sabe to customize your own cowboy hat—a true Aspen tradition and perfect keepsake. For dinner, make a reservation at Zig Zag, the town’s buzzworthy French brasserie. Their steak tartare and lemon chicken are must-orders, and don’t skip dessert—every sweet here is exceptional.

Start your morning with a relaxed breakfast at Sant Ambroeus, a stylish New York export that’s perfect for fueling up before a day on the slopes. Spend the morning skiing Aspen Mountain, and when hunger calls, ski right into Ajax Tavern, an iconic spot at the base of the mountain known for its truffle fries and lively atmosphere.

For those looking for something truly unforgettable, trade a quiet afternoon for the legendary Cloud Nine Alpine Bistro experience on Aspen Highlands. This mountaintop party is like nowhere else in the world—picture champagne showers, a roaring crowd dancing in ski boots, and a DJ spinning as snowflakes fall and the Maroon Bells tower in the distance. The energy here is pure Aspen: glamorous, playful, and over the top. Be sure to book well in advance, as tables go quickly, and prepare for an afternoon you’ll never forget.

As the day winds down, return to town for a chic evening. Toast the day with cocktails and live music at The Snow Lodge at the St. Regis, then indulge in dinner at Matsuhisa, the world-renowned Japanese-Peruvian fusion restaurant by Nobu Matsuhisa—a perfect way to balance the day’s adrenaline with refined, elegant dining.

Rise early and ski straight into Bonnie’s for their legendary apple strudel breakfast—a local favorite that never disappoints. Spend the morning exploring more runs before heading out on a private snowmobiling tour to the breathtaking Maroon Bells, one of Aspen’s most iconic natural wonders.

Back at the Little Nell, warm up with a decadent hot chocolate before enjoying an exclusive private cellar tour and tasting with their expert sommelier. For dinner, dine at Casa Tua, a cozy yet sophisticated spot blending Italian flavors with mountain charm.

Begin your day with breakfast at Bear Den, known for its cozy atmosphere and fresh, wholesome fare. Today, trade Aspen Mountain for Snowmass, where you’ll find expansive runs perfect for a full day of skiing. For lunch, stop at Up 4 Pizza for their legendary pies—a casual yet classic Snowmass experience.

Return to The Little Nell in the afternoon for a restorative après-ski, complete with the hotel’s hot tub, sauna, and an indulgent spa massage. Cap off your Aspen adventure with dinner at Parc, a contemporary alpine restaurant where the menu shines with elevated mountain cuisine—and don’t forget to order their famous donuts for dessert.