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The Boys’ Trip to Aspen Guide

With endless outdoor adventure, world-class dining, and vibrant nightlife, Aspen is the ultimate playground for a boys’ trip, especially in winter. This thoughtfully crafted itinerary delivers the perfect balance of action and indulgence.

 

Skier going off a cliff on Ajax Mountain in fresh powder

 

Thursday – Arrive to Aspen

Arrive at MOLLIE Aspen and settle into your rooms, where check-in starts at 4 PM. Kickstart the weekend with a quick sweat in the fitness center before heading out for your first night on the town.

Dinner at Catch Steak Aspen, for a classic steakhouse mixed with an energetic vibe. Afterward, continue the evening with post-dinner drinks at Silver City Aspen, a local favorite for casual drinks in a Western bar.

 

King Room at MOLLIE Aspen

 

Friday – Powder, Après & Live Music

Start the day with a nourishing breakfast at Petit Trois Aspen, then head to Aspen Highlands, famed for its legendary bowl and challenging terrain.

By mid-afternoon, shift into après mode at Highlands Alehouse, where hearty bar food, patio seating, and live music capture Aspen’s spring ski spirit. Continue the celebration back at MOLLIE for the Martini & Frites Après before returning to Petit Trois for dinner.

Cap off the night with a live performance at Belly Up Aspen, one of the country’s most iconic intimate concert venues, then ease into Aspen’s nightlife scene.

 

Martinis and Frites in the MOLLIE Roof Terrace Bar

 

Saturday – Adventure & Iconic Views

Grab coffee and pastries in the MOLLIE Cafe before skiing a half day on Aspen Mountain (Ajax). Break for pizza at Mt. Rubirosa Aspen at the base of Ajax, then trade skis for engines with a snowmobiling tour at T‑Lazy‑7 Ranch, to the renowned Maroon Bells.

Back at MOLLIE, unwind in the rooftop spa pool with breathtaking views of Aspen Mountain before dinner at Jing Aspen, known for its lively energy and Japanese-inspired cuisine.

 

A snowy evening view of the spa pool on MOLLIE's roof terrace

 

Sunday – A Relaxed Send-Off

Sleep in and ease into the morning with breakfast at Poppycock’s Aspen in downtown Aspen, a longtime favorite for hearty classics. From there, check out of MOLLIE and head home—rested, recharged, and already planning the next trip.

 

Male Guest outside of MOLLIE Aspen

 

Gather your crew for an unforgettable Aspen getaway. From sun-drenched runs to vibrant après, MOLLIE places you at the center of it all. Book the Ski Break Package to enjoy 25% off your stay plus a $25 Food & Beverage credit, the perfect fuel for your spring adventures.

 

Skiers at the bottom of Ajax Mountain
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