The Fillmore Miami Beach ★ 4.4
$$$$
South BeachMon-Thu varies by show, Fri-Sat 19:00 doors, varies, Sun varies by show.
The Fillmore Miami Beach at the Jackie Gleason Theater is the 2,200-seat Art Deco hall on Washington Avenue where Live Nation books touring rock, hip-hop, Latin and comedy acts through the year.
TipOrchestra rows behind the soundboard sound best. Doors usually 19:00 with show at 20:00; Lincoln Road parking garages are the easy lot.
Olympia Theater ★ 4.3
$$$$
Downtown MiamiMon-Thu varies by show, Fri-Sat doors typically 19:00, Sun varies by show.
The Olympia Theater on East Flagler is the 1926 Vaudeville and silent-film palace that now runs as a 1,567-seat concert and performing arts room in central Downtown Miami.
TipSightlines are best from the center mezzanine. Parking is easier at the InterContinental garage two blocks east toward Biscayne.
Churchill's Pub ★ 4.2
$$$$
Little HaitiTue-Wed 20:00-02:00, Thu-Sat 20:00-03:00, Sun 20:00-02:00. Closed Mon.
Churchill's Pub on NE 2nd Avenue is the Little Haiti punk, metal and noise room founded by Dave Daniels in 1979 that reopened in September 2025 after a five-year hiatus.
TipAll-local lineups dominate the calendar since the reopening; the patio out back is the cooler-off spot between sets.
Sugar ★ 4.5
$$$$
$20 cocktails, no cover, upscale casualBrickellMon-Wed 16:00-01:00, Thu-Sat 16:00-02:00, Sun 16:00-01:00.
Sugar on the 40th floor of EAST Miami at Brickell City Centre is the Asian-tropical garden rooftop, lush planting around the deck and panoramic skyline views across Brickell and the bay.
TipNo reservations; arrive before 19:00 weeknights or expect to queue for the elevator. Weekend lines are easier earlier.
Rosa Sky Rooftop ★ 4.3
$$$$
$18 cocktails, small plates from $15, smart casualBrickellMon-Wed 16:00-00:00, Thu 16:00-01:00, Fri 16:00-02:00, Sat 13:00-02:00, Sun 13:00-00:00.
Rosa Sky on the 22nd floor of the AC and Element Hotel Brickell is the dual-brand rooftop lounge with panoramic Magic City views, a street-facing elevator and a small plates and cocktails menu.
TipTake the SW 1st Court elevator straight to the roof. Reserve via OpenTable for sunset; happy hour drinks land before 19:00.
Astra ★ 4.2
$$$$
$20 cocktails, hookah from $50, smart casualWynwoodTue-Wed 18:00-02:00, Thu 18:00-03:00, Fri-Sat 18:00-04:00, Sun 18:00-02:00. Closed Mon.
Astra on NW 2nd Avenue is the Wynwood rooftop that opened above the mural district, an open-air Mediterranean lounge with hookah, a long bar and skyline views across Midtown to the Edgewater high-rises.
TipReserve via OpenTable for prime sunset windows. The hookah service is part of the experience; weekends enforce a smart-casual dress code.