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Orto Botanico
The towering gingko here is the arboreal pride of Milano, surrounded by (perfectly legal) medicinal plants. An afternoon in their fragrant midst may not add years to your life, but it certainly adds to the overall quality.
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Padiglione d'Arte Contemporanea
Cutting-edge art shows seem right at home in this cutting-edge city. Even a 1993 Mafia-related bombing couldn't daunt the gutsy PAC, which arose from the ashes in true Milanese fashion to mount ever more daring shows. Expect to see large, experimental works in new media.
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Palazzo della Ragione
Founded in 1228 to handle deals brokered and broken in this merchants' piazza, this elegant colonnaded hall of justice bears Milan's bristled boar insignia in terracotta. Empress Maria Theresa added a layer of bricks and bureaucracy with an archive of officially notarised papers, which piled up until 1961. Now the Palazzo hosts temporary exhibitions that don't mind being upstaged by their surroundings.
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Palazzo Reale
Talk about versatile: Milan's medieval Town Hall became a Visconti villa in the 13th-century, Spanish hacienda in the 16th, Empress Maria Theresa's palace in the 18th, and World War II bombing target. Now it's being remodelled to house Milan's art collections. Meanwhile, the ground floor hosts touring exhibitions ranging from Helmut Newton: Sex & Landscapes to Caravaggio.
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Parco delle Basiliche
Dodge the shoppers along Corso Porta Ticinese and take the scenic route from San Lorenzo past the Museo Diocesano to Sant'Eustorgio, past couples, clusters of gossips, and children running circles around their parents.
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Parco Sempione
Everything you'd expect from Milan is here: a historic castle (Castello Sforzesco), chic bars, a museum honouring design (Triennale), lovely Liberty-style buildings (Acquario) and an architectural conversation piece (Torre Branca). And there's grass too.
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Photology
Tear yourself away from the gorgeous photography catalogues in the storefront bookstore and check out the gallery out back in the garden shed, where those X Portfolio fetish shots that got Robert Mappelthorpe censored in the US recently shared wall space with bored nudes in mod wigs by Andy Warhol and Carlo Mollino.
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Pirelli Skyscraper
The upstart that broke the rules and outgrew the Madonnina atop the Duomo is widely admired for its fine bone structure: glass skin pulled tautly over a carefully calibrated, reinforced concrete base. Lead architect Gió Ponti's landmark has not only stood the test of time for 50 years, but even withstood an accidental plane crash into the building in 2002.
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San Bernardino alle Ossa
Don't look now, but there are Milanese clamping onto window ledges with their teeth here as though their lives depend on it. Luckily, that's not the case: all of them were long dead when their skeletons were repurposed to make rococo crown mouldings of skulls in this exquisitely morbid 17th-century chapel, through the main church on your right.
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San Francesco di Paola
Tucked in among sprawling temples to fashion in the Quadrilatero d'Oro, this little gem of a church outshines Armani's glittering megastore across the street. Although commissioned by the Minimi order in 1728, it's hardly minimalist, but tricked out in Baroque pomp with gilt galore, a graceful 1890 neoclassical façade, and a chapel altarpiece by Guerini.
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San Lorenzo alle Colonne
Like charming old gents chatting on the front steps weekdays, this place has only got better-looking since the fall of Rome. A freestanding row of 16 Corinthian columns salvaged from Milan's pagan past hints at the crumbling Roman grandeur inside, including the octagonal Cappella di Sant'Aquilino's expressive 4th-century mosaics of big-eared saints.
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San Maurizio
Through a door by the altar lies Milan's hidden crown jewel: the restored 16th-century royal chapel. Bernardino Luini's breathtaking frescoes immortalise the star of Milan's literary scene at the time, Ippolita Sforza, and her family, alongside amazingly blissful martyred women saints - note Santa Lucia calmly holding her lost eyes, and Santa Agata casually carrying her breasts on a platter.
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Sant'Eustorgio
Like Milan's fusion restaurants, this façade is a mish-mash of styles that somehow works. Sant'Eustorgio was built in the 9th century, updated in the 11th, boosted with Bramante's baptistery in the 15th, and given a neo-Romanesque look in the 19th; today, its harmonious exterior belies its rabble-rousing past as Milan's Inquisition centre.
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Spazio Oberdan
Art-house cinema downstairs, art gallery upstairs: Spazio Oberdan is artistically ambidextrous, with video art to bridge the two. Ambitious programs include Ecce Uomo , a show of blockbuster artists feeling Jesus' pain, from Damien Hirst's wry Dead Ends - a medicine cabinet full of cigarette butts smoked religiously - to William Kentridge's animated waves of grief in Tide Table .
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Stazione Centrale
Some call it mighty, others call it mighty ugly, but the 1931 Central Station is certainly the most unavoidable monument in Milan. Nearly 100 million people every year pass through these hulking portals, up escalators past Fascist mosaics extolling the virtues of Lombardy (mostly culinary), and onward to train platforms and parts unknown.
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Studio Museo Castiglioni
Discover where great Italian designs come from at the studio of the Castiglioni brothers, whose historic designs range from the streetlight-turned-pendulum Arco floor lamp for Flos to cheeky downward-spiralling Alessi ashtrays. See prototypes from its 1960s-80s heyday and the objects that inspired them, including bicycle seats and toys made of Iranian beer cans.
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Torre Branca
The spindly legs on this steel tower may not inspire you to take the 10-minute lift ride 108 metres to the viewing platform, but not to worry: Gió Ponti's 1930s engineering feat was safety-reinforced in 2003. Go at night to watch lights twinkle, and lord it over the Just Cavalli Caffé bouncers below.
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Torre Velasca
Is this top-heavy tower the headquarters of some superhero's archnemesis, a postmodern prison block or a watchtower for companies paranoid about corporate espionage? Studio BBPR's signature tower with a bigger, medieval-style block grafted on top was finished in 1958, and almost half a century later, it's still fascinatingly sinister.
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Triennale di Milano
Aficionados of architecture, design and popular culture may have to be pried away from this place with a specially-designed crowbar. Home to the Permanent Collection of Italian Design, the Triennale also features four or five other exhibitions at once, all ingeniously presented: floating helium speech balloons explained a recent show on comics, while Le Corbusier's prefab house was set up on the lawn.
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