Jucy Lucy at Matt's Bar on Cedar Avenue — cheese-stuffed burger that rewrites the rules. Surly Brewing's taproom in Northeast for a flight and the view of the Stone Arch Bridge. First Avenue for a live show (Prince's old haunt). Spoon & Stable in the North Loop for a three-course dinner that lands somewhere between fine dining and a chef's fever dream. Day trip to the Boundary Waters Canoe Area Wilderness with Wilderness Outfitters for a half-day paddle and portage, then back to the city for late-night karaoke at Cowboy Jack's.
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.