1889 silver-boom Aspen original — built by Jerome B. Wheeler (Macy's co-owner), first elevator in town, on the National Register. Auberge Resorts owns it now (heritage preserved, modern amenities layered in). The bachelor's anchor: J-Bar (oldest bar in Aspen, the Aspen Crud cocktail invented during Prohibition — bourbon and ice cream, sounds wrong, drinks right). Day-one Aspen Mountain skiing or summer hiking via the gondola, dinner at Prospect (the hotel's signature). Day two: Snowmass for the longer runs, après at the J-Bar, dinner at the Little Nell or Element 47. Day three: a Maroon Bells trip if summer or a final ski morning. Aspen-Pitkin (ASE) is direct from many hubs; Eagle (EGE) is 90 minutes for the redirect.
Five quick questions, then we build the full itinerary — lodging, daily schedule, dining, bars, the group-chat message — and drop you into a Trip Room you can share with the crew.