Ole Red Orlando ★ 4.0
$$$$
Icon ParkMon-Thu 11:00-00:00, Fri-Sat 11:00-02:00, Sun 11:00-00:00.
Ole Red Orlando on International Drive at ICON Park runs daily live country music across three stories, with a kitchen, balcony stage and a rooftop bar program.
TipFree admission; reserve a balcony table for sit-down shows on Friday and Saturday.
Hanson's Shoe Repair ★ 4.7
$$$$
DowntownTue-Sat 17:00-02:00. Closed Mon/Sun.
Hanson's Shoe Repair on East Pine Street downtown is the rooftop tiki speakeasy with a daily Instagram password, behind a Prohibition-style shoe-repair facade.
TipFollow @hansonsshoeshop for the day's password; arrive before 21:00 to skip the line.
Capa at Four Seasons ★ 4.6
$$$$
Disney SpringsDaily 17:30-22:00.
Capa at the Four Seasons Resort Orlando is the seventeenth-floor Spanish steakhouse and rooftop bar, with paella, charcoal-grilled steaks and Disney fireworks views.
TipBook a window or terrace table at 20:30 for the EPCOT fireworks at 21:00.
Mathers Social Gathering ★ 4.4
$$$$
DowntownTue-Sat 17:00-02:00. Closed Mon/Sun.
Mathers Social Gathering on South Magnolia Avenue is the third-floor speakeasy in the Mathers Building, behind a bookshelf and velvet ropes, with prohibition cocktails.
TipTake the back-of-building elevator; reservations recommended for groups over four.
Southern Nights Orlando ★ 4.4
$$$$
Milk DistrictTue-Sun 21:00-02:00. Closed Mon.
Southern Nights on South Bumby Avenue in the Milk District is Orlando's flagship LGBTQ dance club, with packed drag shows, dance contests and a young queer crowd.
TipFriday and Saturday drag shows start at 23:00; arrive by 22:30 for a good view.
Lil Indies ★ 4.5
$$$$
Mills 50Mon-Sat 17:00-02:00. Closed Sun.
Lil Indies on North Mills Avenue is the listening-bar side of Will's Pub, with a craft cocktail program, low-volume vinyl nights and an indie back-room crowd.
TipSunday vinyl listening nights start at 20:00; arrive by 19:30 for a barstool.