Santeria Toscana 31 fills a former car dealership on Viale Toscana with a 1,500-capacity live room, restaurant, courtyard and bookshop, the second venue of the Santeria cultural project that runs jazz, indie, comedy and electronic across a near-nightly programme.
Tip: Sunday brunch and the courtyard aperitivo run alongside the headline shows; the Jazz in the Corner residency through autumn books the smaller stage. Tickets via the site.
Address: Viale Toscana 31, 20136 Milano
Fabrique opened in 2014 in a former Mecenate industrial shed with a 3,200 capacity and a touring booking calendar that places it alongside Alcatraz as Milan's primary mid-size concert hall, running indie, rock, electronic and rap bills almost year-round.
Tip: Tram 27 stops at Via Mecenate Via Fantoli a 200 metre walk from the door; the standing pit is the floor for headline acts, and the balcony gives sightlines for taller patrons.
Spirit de Milan runs across 1,500 square metres of the former Cristallerie Livellara glassworks in Bovisa, programming live swing, jazz, blues, tango and cabaret nightly alongside a Lombard kitchen, with a dance floor that hosts the Holy Swing Night every Wednesday.
Tip: Bovisa FNM is the closest train stop. The swing nights pack out for the lindy hop crowd; book a dinner table to lock in a seat before the first set.
Bar Magenta has run on the corner of Via Carducci near Sant'Ambrogio for over a century, with an Art Nouveau room, tiled floors and a late-running counter that hosts small live music nights, songwriter sets and a student-heavy aperitivo through the week.
Tip: Open into the small hours daily; the live music programme is small-stage and acoustic-leaning. Coffee, beer and tramezzini are the daytime stock.
Ceresio 7 opened in September 2013 on the penthouse of the former Enel headquarters in Isola, designed by Dimore Studio for Dean and Dan Caten of Dsquared2, with two outdoor pools, twin terraces and 360-degree sightlines across the Bosco Verticale and Unicredit Tower.
Tip: Cocktails run around 22 euros and pool access is dining-guest only; book the terrace at sunset for the strongest light on the skyline. M5 Monumentale is the closest metro.
Radio Rooftop sits on the tenth floor of the ME Milan Il Duca hotel above Piazza della Repubblica, with a wraparound terrace, daily DJ sets and a cocktail programme that runs alongside the Aldo Rossi-designed lobby below.
Tip: A dedicated lift on Via Marco Polo bypasses the hotel reception; book the outdoor terrace for the skyline sightline rather than the indoor lounge.
Terrazza Aperol crowns Il Mercato del Duomo on the corner of Piazza del Duomo and Galleria Vittorio Emanuele II, with a second-floor terrace pointed at the cathedral facade and a kitchen that pairs aperitivo plates with the canonical Aperol Spritz.
Tip: Walk-in tables on the terrace go to the patient queue on weekend evenings; reserve via the site to lock in a Duomo-facing seat at sunset.