Miami

Wynwood Rooftop Flips Hip-Hop Classics Into Late-Night Jazz Heat

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Published on April 29, 2026
Wynwood Rooftop Flips Hip-Hop Classics Into Late-Night Jazz HeatSource: Google Street View

Wynwood is getting a new way to stay up late this Friday, when On & On, a rooftop hangout above Shiso, starts turning hip-hop favorites into live, slow-burn jazz and R&B. The intimate patio is set to host two short sets every Friday night, blending live instruments, DJs and rotating vocalists for crowds that are in no rush to call it a night.

According to Miami New Times, On & On will operate on the patio above Shiso Asian Smokehouse at 239 NW 28th St and build its whole identity around "soulful jazz interpretations" of hip-hop classics. The outlet notes that Friday programming is split into two sets and that the early May lineup already includes vocalists Maya Azucena and Alexander Star.

Forward Hospitality Group, which runs Shiso, describes the new concept as an intimate live spin on hip-hop, paired with a cocktail-driven bar and semi-private cabanas. That framing comes from a preview in Modern Luxury, which also spotlights the cabanas and the rooftop bar program as part of the draw.

The musical side is in the hands of Stephen Tate, co-founder of Miami Jazz Booking, a local agency that specializes in jazz, funk and soul acts across town. Organizers say Tate is pulling from his roster to strike a balance between improvisation and familiar, crowd-pleasing takes on recognizable tracks.

Lineup and schedule

Event listings show Maya Azucena on deck to launch the series on May 1, with Fridays booked out through the rest of the month and Alexander Star scheduled to appear later in May. The Maya Azucena date is posted on platforms including Shazam, while Alexander Star's appearances show up on Apple Music and other ticketing sites.

Food, drinks and vibe

The rooftop itself sits on top of Shiso, the Forward Hospitality Asian smokehouse that opened in Wynwood with wood-fired cooking, a 6,500-square-foot rooftop outfitted with cabanas and a racetrack bar. PROFILEmiami detailed Shiso's menu and rooftop footprint, laying out how a live music program fits into a space already designed to feel theatrical.

On & On arrives as Wynwood keeps stretching its nightlife options, leaning harder into curated live music for people who want more than just a DJ playlist. With reworked hip-hop standards, a cocktail-heavy bar and Shiso's rooftop stage all stacked together, backers are betting this spot becomes one more reason to linger in the neighborhood after dark.