Downtown Orlando works best as a sequence: dinner, a band, then somewhere to talk about the band. These rooms are all a short walk apart.
Before: Kres Chophouse sits in the 1930s Kress five-and-dime, where Black residents held lunch-counter sit-ins in 1960; reservations cap at six. Reyes Mezcaleria up Orange Avenue pours more than 150 agave spirits.
The show: The Beacham, established 1921, calls itself Orlando's longest running independent venue. Its smaller sister, The Social, shares the box office.
After: Hanson's Shoe Repair is a rooftop speakeasy on what may be the oldest building downtown; you need the day's password. Mathers and The Phoenix Jazz Club stack a cocktail room over a listening lounge in an 1864 building, with a dress code. Bellhop in the old Angebilt Hotel is open until 2 a.m. on weekends and pitches itself for a quiet drink.
Gone from older lists: Tanqueray's closed in April 2026 and The Robinson's space is now a different bar. Everything we track downtown is on the neighborhood page.