Macondo runs a Pratello cocktail bar with a tiny stage that programmes around 250 live nights a year, anchoring Via del Pratello's bohemian strip with Italian songwriters, indie sets, folk acts and the occasional jazz quintet from 21:30.
Tip: The room fills by the second song so arrive by 21:00 for a bar stool. Cash and card both work and the cocktail list runs cheaper than the centre.
Address: Via del Pratello 22c, 40122 Bologna
Terrazza Mattuiani opens for the warm months on the fifth floor of Hotel Touring Bologna with a cocktail bar, loungers and an in-deck jacuzzi, looking across the rooftops toward San Petronio and the Two Towers a few streets north.
Tip: Reservations are required; the jacuzzi slot runs 30 minutes per booking. Open May through September only, hours can shift if the weather closes the deck.
The Roof Garden sits on the fifth floor of Hotel Metropolitan a couple of streets from Via dell'Indipendenza, with loungers, dining tables and a sightline that runs from San Luca on the hill to the Bologna rooftops.
Tip: Aperitivo runs from 17:00 and the kitchen sends a short bites list at the bar. Closed October to February so plan for the warm months.
The Aemilia Hotel rooftop runs from the seventh floor of the Savhotel on Via Zaccherini Alvisi, a wide terrace with a lounge corner and a panorama that takes in San Luca, the Two Towers and the eastern university quarter beyond Porta San Vitale.
Tip: The hotel sits a 10 minute walk east of the centre; the terrace is quieter than the central hotels and the cocktail list runs cheaper. Sunset over San Luca is the time slot.
I Portici tucks its rooftop deck above a 19th-century palazzo on Via dell'Indipendenza, with a cocktail bar that looks across the green of Parco della Montagnola toward the hills and a separate Michelin-listed dining room two floors below.
Tip: Cocktails from 18:00 with a short bar menu; the room downstairs takes the dinner crowd so the rooftop stays drink-only. Reserve through the hotel for a terrace seat.
The Donkey hides a small cocktail room behind a medieval gate on Vicolo Broglio, pairing a no-oversized-drink rule with a curated spirits back bar, a short cigar list and an art deco interior that splits Art Nouveau and 1950s modernist cues.
Tip: Reservations only via WhatsApp to 349 138 4953; the door does not take walk-ins. Cocktails sit around 14 euros, sized to the spirit-forward house style.
Le Vie dei Briganti sits on Via Alessandrini above the Moline canal, with an upstairs bistro and a basement speakeasy reached by ringing a hidden bell, run by four Roman owners with a cocktail list that swings prohibition classics into Italian flavours.
Tip: Daytime food service runs upstairs; the underground bar opens for evenings only. Ask the bartender about the canal-window seat, a small basement banquette with the Moline view.