Miami's music sits in two histories at once. Overtown was Little Broadway, the Lyric Theater opened in 1913 and the Hampton House put up Ali, Malcolm X and Sam Cooke when the Beach hotels would not, and Little Havana has been playing live Cuban sets on Calle Ocho since Ball & Chain opened in 1935. Add Dante's HiFi, Miami's first Black-owned vinyl listening bar, and the free Monday jam at Churchill's, and there is a room every night of the week.
Tap a gold pin to see the club and jump to its card below.
Built in 1913 and the last theater standing from Overtown's Little Broadway, where Ella, Basie and Cooke played after the Beach hotels sent them back across the tracks. The Spam Allstars-era jazz orchestra plays first Fridays at eight.
Pip’s Tip Built 1913, the last house on Little Broadway
The Green Book motel where Muhammad Ali celebrated the Liston fight with Malcolm X, Sam Cooke and Jim Brown. Restored as a museum and cultural center, it runs Victor's Jazz Supper Club on select Saturdays in the original room.
Pip’s Tip The Green Book motel, Ali, Malcolm X, Sam Cooke
Marcus Samuelsson put his Miami room on the same block where Little Broadway once hummed. Sunday Jazz starts at five with no cover, Boogie Down Thursdays run later, and the cornbread is worth the trip on its own.
Pip’s Tip Sunday Jazz from 5pm, no cover
The third Friday of every month, the courtyard fills for Sounds of Little Haiti, konpa, rasin and jazz, food vendors, free admission and a crowd that spans four generations. The single best free night in Miami.
Pip’s Tip Sounds of Little Haiti, third Friday, free
Miami's first vinyl listening bar, with 8,500 records and Rich Medina as music director steering soul, funk, jazz, house and hip-hop through a sound system built for it. Small, dark, and best after midnight.
Pip’s Tip Miami's first Black-owned vinyl listening bar
A real jazz house on Miracle Mile running seven nights a week with three sets a night and a five-dollar cover. Straight-ahead, well-played and refreshingly unfussy, the room Miami had been missing.
Pip’s Tip Seven nights a week, sets at 6, 8 and 10
Open since 1935, when Billie Holiday, Count Basie and Chet Baker played a Calle Ocho room that would book them. The pineapple bandshell in the back patio still runs live Afro-Cuban and salsa nightly.
Pip’s Tip Open since 1935, Billie Holiday sang here
A World's 50 Best bar where the cantineros flip shakers in time with a live Cuban band. The floor between the tables becomes a dance floor around eleven, and nobody plans it that way.
Pip’s Tip Cantineros and a live Cuban band, nightly
The Calle Ocho room where Cuban exiles built a Miami son and filin scene, back open since 2024. Small, warm, packed on the right nights, and completely uninterested in impressing tourists.
Pip’s Tip Reopened 2024, still the real thing
Named for the Hemingway line and decorated like it, with a long bar, Cuban plates and live music that keeps the room moving. A good first stop on a Calle Ocho night.
Pip’s Tip Hemingway styling, live Cuban sets
Coral Gables' Saturday-night jazz institution, running the same standing gig since 1996 with no cover charge. Sidewalk tables, a bar three deep by ten, and a band that has played together long enough to show it.
Pip’s Tip Saturday jazz since 1996, no cover
Pick a bottle off the shelf, cut some cheese, take a folding chair on the grass and let the band play. Live jazz, blues and soul every single night in a string-lit backyard that feels borrowed from New Orleans.
Pip’s Tip Live band nightly in a string-lit backyard
A supper-club-shaped room just off the Design District where the kitchen is taken as seriously as the bandstand. Come for dinner, stay through the set, leave later than you meant to.
Pip’s Tip Dinner and a set, off 46th Street
Miami's underground institution since 1979, back open after five dark years. Monday's free Miami Jazz Jam is where the city's players actually come to blow, and the rest of the week is loud in other ways.
Pip’s Tip Free Miami Jazz Jam every Monday
A downtown corner bar that runs to five in the morning and gives Tuesday nights over to jazz. Free, unpretentious, and full of people who came for the music and stayed for the hours.
Pip’s Tip Tuesday jazz, and the bar runs till 5am
A bohemian Italian room hidden off Flagler with mismatched art on every wall and jazz on Thursday nights from seven. Order the pasta, sit close to the band, and forget you're downtown.
Pip’s Tip Thursday jazz in a downtown hideaway
The Betsy programs live jazz nine times a week and never charges a cover, which makes this the most reliable jazz address on Ocean Drive. Small room, good players, grown-up crowd.
Pip’s Tip Live jazz nine times a week, no cover
A jazz bar inside a restored Collins Avenue hotel, running Thursday through Saturday with the kind of intimate staging South Beach almost never offers anymore. Dress a little.
Pip’s Tip Thursday through Saturday on Collins
An open-air amphitheater a block from the sand, programmed by the Rhythm Foundation with more than 140 shows a year, jazz, Afro-Caribbean, Haitian, Brazilian and everything adjacent. Check the calendar before every Miami trip.
Pip’s Tip 140+ shows a year, ocean at your back
Sitting in Peacock Park under the banyan trees with the bay just past the grass, this is where the Grove does Jazz in the Park. Bring people who don't think they like jazz.
Pip’s Tip Jazz in the Park, under the banyans
Built in 1913 on Little Broadway and brought back by the Black Archives, the last house standing from Overtown's golden age.
Jazz is one chapter of Pip's Lifestyle, find the lounges, whiskey bars, rooftops and the Domino Club below.
