Porta Romana & Porta Vittoria in Milan

These neighbouring districts make a useful counterpoint. Porta Romana retains an old-school Milanese ease, with family businesses and traditional food, while Porta Vittoria is gaining a younger, more experimental rhythm. You can spend the day moving between a former cemetery, a restored lido, a historic dance hall and a major contemporary-art complex, then stay for aperitivo or dinner.

Getting around Porta Romana and Porta Vittoria

Use Porta Romana on the M3 yellow line for QC Termemilano and the Bagni Misteriosi pools. Continue to Lodi TIBB on the same line for Fondazione Prada. Tram 9 runs around Viale Premuda and is the useful choice for the Rotonda della Besana; trams 12 and 27 follow Corso di Porta Vittoria and Corso XXII Marzo.

Porta Vittoria is also the main station for the Passante, Milan's underground railway. The service links this part of the city with the wider metropolitan area, so it is useful when your route begins outside the central metro network.

Fondazione Prada

A former gin distillery now houses Fondazione Prada, an art complex designed by Rem Koolhaas. The architecture is deliberately polished and theatrical, but the collection supplies the real reason to stay: Jeff Koons' tulips and Carsten Höller's playful mushrooms are among the memorable contemporary works on view.

Haunted House

The four-storey Haunted House is difficult to miss: its exterior shimmers beneath a covering of gold leaf. Inside, a permanent installation by Robert Gober shares the building with two works by Louise Bourgeois. Bourgeois' Cell (Clothes; 1996) turns personal belongings into an intimate meditation on the artist's past. Gober's disorientating Arms and Legs Wallpaper (1995-2015) and Corner Door and Doorframe (2014-15) make ordinary architectural details feel uncertain.

Studio d'Orphée

In the Sud (South) gallery, Studio d'Orphée recreates the living and working environment of French director Jean-Luc Godard. Film-editing equipment and a screen showing his short films sit beside the personal objects that made the studio-house in Rolle, Switzerland feel lived-in: a leather chair patched with gaffer tape, a hat stand, books and framed paintings. The title compares Godard with Orpheus, the musician and poet of Greek legend.

Processo Grottesco

Thomas Demand normally destroys his paper constructions after photographing them. Processo Grottesco is the exception. Built for his photographic work Grotto, the surviving installation uses a computer-guided process to cut and layer 30 tons of grey cardboard into an almost life-sized version of a grotto in Mallorca. Postcards, advertisements and books about the grotto help reveal how the artist built the illusion.

Atlas in the Tower

The 60m-high Atlas tower is the complex's most ambitious building. Each of its nine floors has a distinct design, and the storeys grow taller as you rise. Six levels contain the permanent collection. Highlights include Damien Hirst's ominous, fly-filled The Last Judgement and Carsten Höller's enormous Alice-in-Wonderland-style mushrooms, reached after a walk through darkness that makes them even more surprising.

Walk Porta Romana and Porta Vittoria

This 4.8km route takes about 2½ hours and moves from the polished, traditional side of Porta Romana toward the newer energy of Porta Vittoria. It begins with a Milanese breakfast, passes a former cemetery and long-established shops, then ends at the contemporary art complex that has helped put the railway edge on the cultural map.

1. 01Start at Pasticceria Sissi, a breakfast address favoured by Milan's more polished crowd. Work through the fur coats to find a place in the leafy courtyard, then order the house croissant, whose filling carries a discreet note of marmalade. Before continuing, take the short detour to Via Lincoln and its pastel-painted houses, a miniature Milanese echo of London's Portobello Road.
2. 02At Rotonda della Besana, trade the noise of the streets for neat lawns and a covered walkway. The portico's capitals still carry small skulls, reminders of the site's former use as a cemetery. The old church now contains MUBA, an art centre for children, as well as a small bistro.
3. 03Turn into Via Orti, one of the area's most appealing streets. Salumeria Drogheria Cassani has remained with the same family for more than 100 years and is ideal for browsing. For a full plate, sit at the red-checkered tables of La Bettola di Piero and order generous Milanese comfort food.
4. 04The traffic around the Imperial Gate cannot hide its history. The gate was part of the Spanish walls and was completed in 1596 for the arrival of Lady Margaret of Austria, who was travelling to marry Philip III of Spain. It is the grandest surviving reminder of Milan's old city entrances.
5. 05Cascina Cuccagna offers a rural pause without leaving the city. The former farmhouse now combines a bar, restaurant, guesthouse, bookshop, plant shop and event space, with a vegetable patch and garden. On some dates it hosts craft and farmers markets; otherwise, find a sunny corner for a drink and handmade snacks made with local ingredients.
6. 06Finish at Fondazione Prada, where Rem Koolhaas transformed the former distillery into a place for contemporary art and striking architecture. If you want a second exhibition after the Prada visit, nearby Fondazione ICA presents focused projects that can range from ceramics to cinema.

Experiences and neighbourhood sights

QC Termemilano

Behind Spanish walls dating from 500 CE, QC Termemilano turns a former Art Nouveau tram depot into Milan's elaborate spa retreat. Entry is €52-78. Put on the supplied fluffy robe and choose between a bio sauna inside a historic pine-lined tram, open-air whirlpools beside the ancient walls, or a darkened room filled with soft music and aromatic scents. The boldest option is an immersion in ice-cold water. Massages are available on the floor above, but they must be booked in advance.

Early morning is the quietest time if you want an unhurried sauna. On Friday and Saturday nights, the pools often become more intimate about an hour before closing as couples settle in. Leave by 10pm if you would rather avoid that atmosphere.

Bagni Misteriosi

Architect Luigi Secchi designed Bagni Misteriosi as a community centre in 1939. After the modernist lido was abandoned in 2007, a careful restoration brought back its huge heated pools, close-cut lawns, shaded porticos, bistro and bar. Today Bagni Misteriosi is once again a favourite summer escape; prices vary. Swimming continues until 10pm on selected nights, and the neighbouring Teatro Franco Parenti adds dance and music performances.

The most enjoyable summer window is 6.30pm-9pm, when you can take an aperitivo beside the pool without shoes. One pool has a flamingo fountain and is reserved for children; the Olympic-sized pool is for adults only. Changing rooms are notably good, lifeguards are on duty and the playlist keeps the mood lively. The bar and bistro can also be entered from Via Sabina without paying for pool access. In winter, the complex becomes a brightly lit ice-skating rink.

Chiesa di Santa Maria dei Miracoli e San Celso

The ornate Renaissance facade of Chiesa di Santa Maria dei Miracoli e San Celso is unusually mannerist for Milan, with statues covering its surface. Entry is free. The church's emotional centre is a 15th-century fresco of the Madonna and Child at the left altar. According to the story, in 1435 the Madonna stepped out of the image and extended the infant Jesus toward a crowd of 300 people, ending the four-year plague that had devastated Milan. Newlyweds still ask for her blessing and leave flowers.

Inside, vivid frescoes by Bergognone, Procaccini and Appiani give the church a jewel-like colour. Outside, Cesare Cesariano's four-sided portico reinforces the building's grandeur. Next door is one of the original 11th-century chapels on the site, where St Ambrose is said to have found the remains of the Roman martyrs Nazaro and Celso.

Balera dell'Ortica

Traditional balere once served as Italy's equivalent of a modern club, with young people meeting to dance the tango, waltz and liscio, the northern Italian style. Balera dell'Ortica was close to disappearing until the Di Furia family gave it a new lease of life. Rock 'n' roll, swing, Lindy Hop and liscio nights now attract a new generation, and classes run throughout the year. Even non-dancers have reasons to come: there is a bocce area, a vintage market and a restaurant serving homestyle Italian food.

Rotonda della Besana

The Rotonda della Besana occupies a former 17th-century cemetery for the poor, once said to have received nearly 150,000 burials when the site stood outside the city. Its present mood is entirely different. People read, picnic and stretch out on the lawns inside a circular late-Baroque enclosure, while a raised path under the graceful portico provides a shaded walk.

At the centre, the deconsecrated church of San Michele houses MUBA, Milan's first arts and culture centre for children (adult/child €8/10). The chic Rotonda Bistrot (rotondabistro.com) serves drinks beneath the church's Ionic columns. Look closely at the capitals around the portico and inside the church: discreet skulls are the remaining signs of the cemetery's darker past.

Listings: eating, drinking and shopping

The price marks are simple: € indicates budget, €€ midrange and €€€ top end. Opening times below reproduce the published patterns for each place, so check before making a special journey.

Eating

Sweets and pastries

• ✦Pasticceria Sissi € - This pastry shop, run by an Italo-Senegalese family, is a morning meeting point for Milan's well-dressed regulars. Order a sweet or a custard-filled croissant and look for a table in the courtyard. Hours: 6.30am-noon Mon, to 8pm Wed-Sun.
• ✦Loste € - The pastries match the pedigree of this cafe's co-owner, a former head pastry chef at Noma. The sticky cardamom bun is the signature, while the speciality coffee is excellent but expensive. Hours: 8am-3pm.
• ✦Pasticceria KNAM € - Chef Ernst Knam's pastry shop is known across Milan for chocolate desserts and combinations that take unusual flavour pairings seriously. Hours: 10am-1pm Tue-Sun, 4-8pm Mon-Fri, 3-8pm Sat.

Street food and pizza

• ✦Sidewalk Kitchens €€ - This lively food hall ranges from Japanese curry to an American smash burger, with several street-food counters alongside a speciality coffee and wine shop. Hours: noon-3pm & 6-11.30pm.
• ✦Giannasi dal 1967 € - Dorando Giannasi has been roasting chicken at his Piazza Buozzi stall since 1967. The secret herb marinade is closely guarded, and the food is a reliable Milanese street-food stop. Hours: 8am-8pm Mon-Sat.
• ✦Panificio Davide Longoni € - Davide Longoni is one of the most celebrated names in Italian bread. His compact shop turns out natural-leavened bread, stone-ground loaves, pastries and especially good panini. Hours: 8am-3pm Mon, 8am-9pm Tue-Sat, 8.30am-3pm Sun.
• ✦Modus € - Gambero Rosso has praised this restaurant, where Paolo De Simone brings the flavours of Cilento to Milan through pizzas and generous home cooking such as potato parmigiana. Hours: 12.30-2.30pm & 7-11.30pm.

Gelato

• ✦Pavé Gelati € - Simona Carmagnola makes ice cream with an unusually light, airy texture and keeps changing the flavour list. Coffee and cardamom are two examples of the more distinctive combinations. Hours: noon-midnight Mon-Thu & Sun, 12.30pm-12.30am Fri, noon-12.30am Sat.
• ✦Gelateria Giova € - Giovanni's nickname supplies the name, while the ingredients do the convincing: emerald Bronte pistachios and lemons from the Amalfi Coast are among the highlights. Hours: noon-11pm.

Italian cuisine

• ✦Trippa €€ - Chef Diego Rossi has made cucina povera, or peasant cooking, fashionable again. Tables are hard to secure, so book ahead for the direct, carefully judged dishes. Hours: 7.15-11.30pm Mon-Sat.
• ✦Dongiò €€ - This generous Calabrese trattoria is one of Milan's best-value meals, with spicy southern flavours and homemade pasta in a warm, unpretentious setting. Hours: noon-2.30pm Mon-Fri, 7-11pm Mon-Sat.
• ✦Trattoria del Pescatore €€€ - Sardinian couple Giuliano and Agnese run what is often described as Milan's finest fish restaurant. The Catalan lobster, served with tomatoes and onions, is the dish to seek out. Hours: 12.30-2.30pm & 8-11pm Tue-Sat.
• ✦Stadera €€ - Michelin-starred chef Aldo Ritrovato serves Neapolitan comfort food in a contemporary deli-diner, from parmigiana to pastiera, the ricotta-based cheesecake. Hours: 11.30am-11pm.

Traditional Milanese

• ✦Trattoria Masuelli S Marco €€€ - The Masuelli family has kept this trattoria going for more than 100 years, making it a reference point for Milanese classics such as osso buco with saffron risotto. Hours: 12.30-2.30pm Wed-Sun, 7.30-10.30pm Tue-Sat.
• ✦La Bettola di Piero €€ - The red-checkered tables and textbook trattoria decor could feel like a caricature, but the kitchen delivers serious, uncompromising Milanese home cooking. Hours: 12.15-2pm & 8-10.30pm Mon-Sat.

Upmarket dining

• ✦Autem €€€ - Luca Natalini lets the market decide the menu, changing the elegant dishes daily and treating cooking as a form of art. Hours: noon-2.30pm Thu-Mon, 7-10.30pm Wed-Mon.
• ✦bu:r €€€ - Eugenio Boer's menu is a creative reading of Italian tradition. Familiar dishes are made with local produce and executed with unusual precision. Hours: 12.30-2pm Sat-Sun, 7.30-10pm Tue & Thu-Sun.

Drinking

Atmospheric aperitivo

• ✦Un Posto a Milano - Cooperatives rescued Cascina Cuccagna from dereliction and turned it into a social hub with a guesthouse, bar and restaurant. Come for an aperitivo beside the garden. Hours: 9am-midnight.
• ✦Lacerba - Futurist collectibles and posters fill this intimate bar, a tribute to Milan's most famous and combative art movement. The cocktails are excellent. Hours: 6pm-12.30am Mon-Thu, to 1.30am Fri-Sat.
• ✦Bar Luce - Wes Anderson designed this cafe-bar as if it belonged in one of his films, with Formica tables, pastel colours and vintage pinball machines. Hours: 8.30am-8pm Mon-Thu, to 8.30pm Fri, 9am-8.30pm Sat-Sun.
• ✦Potafiori - Florist and jazz singer Rosalba Piccinni fills this beautiful room with flowers, food and performance. An aperitivo may come with an unexpected burst of song. Hours: 6.30pm-midnight.
• ✦Nottingham Forest - Molecular mixologist Dario Comino gives this eclectic tiki bar its reputation, building elaborate cocktails with smoke, dry ice and considerable imagination. Hours: 7pm-2am Tue-Sat, 6pm-1am Sun.

Wine and craft beer

• ✦Bar Paradiso - Two people from the local Spacedelicious agency turned their enthusiasm for food and drink into an Italian version of a French cave à vin. Expect good wine, local ingredients and a fashion-conscious crowd. Hours: 6pm-midnight Mon-Sat.
• ✦LambicZoon - This craft-beer specialist has collected awards for its unusual wild-fermentation beers, Belgian imports and intriguing Italian sour ales. Hours: 6pm-1am Mon-Thu, to 2am Fri, 12.30pm-2am Sat.

Clubs and live music

• ✦Santeria Toscana 31 - By day this is an eatery and coworking address; at night it becomes a busy bar with live music and DJs playing dancehall and funk. Hours: 6pm-1am Mon-Thu, to 2am Fri-Sat, to midnight Sun.
• ✦Club Plastic - Milan's most historic club began as a hangout for Andy Warhol and Keith Haring. It remains a gay-friendly place for a late night, with Nicola Guiducci at the console. Hours: 11pm-late Wed, Fri & Sat.

Shopping

Independent, vintage and bespoke

• ✦Bezpen - Owner Elisabetta has made this cosy womenswear shop feel like a well-edited version of her living room. Browse independent labels that may be new to you. Hours: 10.30am-2.30pm Tue-Sat, 3.30-7.30pm Mon-Sat.
• ✦Camiceria Olga - This affordable shirtmaker produces custom-tailored shirts in plain fabrics and pinstripes. Embroidered initials add the distinctly Italian finishing touch. Hours: 2.30-7.30pm Mon, 8.30am-6pm Tue-Fri, to 12.30pm Sat.
• ✦Mania Vintage - Handbag collectors should make time for this excellent vintage specialist, whose bags and accessories include high-end names such as Chanel and Louis Vuitton. Hours: 3.30-7pm Mon, 10am-7pm Tue-Sat.
• ✦Fratelli Bonvini - Since 1909, this historic shop has catered to stationery lovers. Its notebooks, calligraphy supplies and rotary pencil sharpeners have a pleasingly old-fashioned charm. Hours: 10.30am-1pm & 2-7.30pm Tue-Sat.

Map index

The neighbourhood map uses letter-and-number squares. The index below keeps the map references attached to every experience, eating place, bar and shop listed in this chapter.