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MILAN

In this land of Gucci loafers and Ferragamo Oxfords, lace up and lash tight a pair of well-worn Merrell hiking boots. Renowned as an epicenter of fashion, this Italian city is also surprisingly walkable, threaded with commerce-canyoned walkways and studded with gems from early Christendom and the Renaissance.

Most of these sights and smells and tastes are centered in the heart of this sprawling city and you could pack them all into one day, but don’t. Take time for primo people-watching opportunities, from sipping an espresso or two outside Princi bakery, to swirling a glass of Mazzei Chianti at an outdoor table on the pedestrian Dante Street, to savoring an aperitif at retro-chic Marchesi above Prada, looking from aloft at the milling multitudes in the majestic Galleria Vittorio shops.

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Start with — as for so many good things Italian — your stomach. Italy Segway Tours offers a culture- and history-infused jaunt for your taste buds in the inviting neighborhood of La Brera. Despite the company’s name, this is a walking tour. That’s preferable, given the cobblestoned chaos that passes as Milan’s streets. You would not want to jockey with the hordes of scooters swooping, locust-like, around drivers.

La Brera removes itself from much of that cacophony. Once a cesspool of vice and prostitution, the neighborhood was reclaimed in the early 1900s by squatting artists. (If you want urban renewal done right, start with starving artists.) As usual, the artists were so successful in making this area over that it became trendy, pushing rents up and booting them out. The Pinacoteca di Brera, the premier art museum in Milan, remains as an academy. And vibrant shops and cafes, beguiling alleyways with plants cascading from iron balconies, and cloistered courtyards attest to the artists’ talents.

La Brera, named in medieval times, means “grazing land.’’ And grazing you’ll do. The tour starts, somehow appropriately, with desserts that rev four of your senses at a corner bakery. By the time you finish six stops later at a gelato stand, you’ll have learned about and tasted how the Parma region is the Kismet to the cuisine of the Mediterranean (slivers of prosciutto and chunks of Parmesan washed down with a local lager), the role of rice, as opposed to pasta, in Northern Italy in such trademark dishes as risotto Milanese (washed down with prosecco), and delectable regional meatballs.

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Fittingly, they delivered the discourse on the national drink of Italy, the mouth-mauling Campari, at a corner hangout for journalists.

Before leaving Brera, duck into the dark ages. The Basilica of San Simpliciano, a fourth-century church, is set back from busy Garibaldi Street. Step in and the bustle of modernity disappears into a dimness flicked only by candles below and filtered sunlight through stained glass above. Here, your breath is felt and heard. It can be transfixing.

The Arco della Pace was initially commissioned by Napoleon as a tribute to his feats in battle. After he was deposed as emperor, the memorial was redesigned to feature a bas-relief of his defeat in battle and statues turned to face away from Paris.
The Arco della Pace was initially commissioned by Napoleon as a tribute to his feats in battle. After he was deposed as emperor, the memorial was redesigned to feature a bas-relief of his defeat in battle and statues turned to face away from Paris. Michael J. Bailey/Globe staff/Globe staff

About two blocks west is Parco Sempione. Once military parade grounds, the park provides a terrific place to work off those Brera calories and soak in some history. Jog on the oval track and climb the thousands of stairs of the neoclassical Arena Civica, site of such disparate events as Buffalo Bill’s “Wild West Show,’’ Inter Milan soccer matches, and concerts by the likes of Radiohead and Lou Reed.

A two-minute jog from the arena is the Arco della Pace. Conceived by Napoleon when he was briefly emperor here, it was intended as an Arc of Victory, a counterpoint to the Arc de Triomphe. (The original road to Paris, still in use through the Alps, ends at the gate of this arch.) Construction on the monument was halted after Napoleon withdrew in 1814, then it was renamed and completed two decades later.

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As you walk through and around the arch, consider: The magnificent statues on horse-drawn chariots atop the monument were originally intended to face France, to welcome Napoleon, but the Milanese turned them so the beasts’ backsides greet Parisians.

Sforzesco Castle, long the stomping grounds of Leonardo da Vinci, features several museums and courtyards, including one with a reflecting pool.
Sforzesco Castle, long the stomping grounds of Leonardo da Vinci, features several museums and courtyards, including one with a reflecting pool.Michael J. Bailey/Globe staff/Globe staff

The park’s other bookend is Sforzesco Castle. This was the stomping grounds and engineering lab for Leonardo da Vinci for about a quarter century. The touches of the poly-master, who died 500 years ago this May, include an intricate, intertwining wall-to-ceiling fresco.

In this lair of Leonardo, however, the most arresting piece is the last, unfinished Pieta by Michelangelo.

Begun a decade before the sculptor’s death, the piece originally featured the fallen Christ and the mourning Madonna as robust, supple figures, as in his most famous pieta, now at St. Peter’s Basilica. But as Michelangelo approached his 90s, he started to wholly rework the piece. The figures became spectral and spindly, almost gaunt; the lines between the supporter and the supportee erased. Remarkably, one of Jesus’s legs and part of the Madonna’s face remain from the original piece; a stunning contrast, vestiges of youth cast against the ages.

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The piece is housed in a simple whitewashed gallery, with fading frescoes from the 16th century. Once a Spanish military hospital, it now encircles a moment of eternal suffering, unrealized yet wholly affecting.

Leonardo’s masterpiece, “The Last Supper,’’ is in the nunnery at Santa Maria delle Grazie, about a 10-minute jaunt from the castle. You’ll need to get reservations online in advance. Each group of viewers is allotted 15 minutes, enough time to soak in the fading aesthetics. Look for da Vinci’s use of geometry to create a sense of depth beyond the wall.

On your return to the city’s center, take two detours, one sacred, the other blessedly profane.

The San Maurizio al Monastero Maggiore has the curb appeal of a granny flat. Three steps inside, however, and floor-to-ceiling frescoes surround you in stunning splendor. Reanimated by a recent three-decade restoration, 16th-century panels unfold the Bible in brilliant colors. As the massive artworks wash over you, make sure you find the portal in the partition behind the altar to where the cloistered nuns worshiped at San Maurizio, which Milanese call their Sistene Chapel. Here reside some of the earliest Renaissance landscapes.

About four blocks away, Piazza Affari is built atop a buried ancient Roman theater. The drama extends into the 21st century.

This is the site of Italy’s stock market, the Borsa, and, like Wall Street, a large statue faces the entry of this symbol of capitalism. The design of the statue was voted upon by the Milanese. But instead of a bull, they chose a bird. As in the kind you flip. The year was 2010 and the Italian economy was in tatters, the markets were melting, and retirement nest eggs were crushed. So residents voted for an apparent one-finger salute to the 1 percent.

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The statue is also a slap at fascists, for the other three fingers are not turned down, but severed, leaving one from the four-finger Mussolini salute.

Dante Street, a wide pedestrian-only connection between Sforzesco Castle and the Duomo, is an ideal place to share a bottle of wine at an outdoor table and watch the world walk by.
Dante Street, a wide pedestrian-only connection between Sforzesco Castle and the Duomo, is an ideal place to share a bottle of wine at an outdoor table and watch the world walk by.Michael J. Bailey/Globe staff/Globe staff

Finish your multi-day hike with a peak experience: Duomo il Milan. Its setting is grand, on a piazza next to the Galleria Vittorio. Yet, it is the building, the fifth-largest Christian church in the world, that will get your heart pounding. Taking 579 years and at least 78 chief architects to complete, the cathedral is one of the jewels of Europe; a canal network was created just to transport slabs of its pink-veined marble from Lake Maggiore 50 miles away.

Also getting your heart pounding will be the 250 steps you’ll take to the Duomo’s terraces. Marvel at dozens of gargoyles, 135 Gothic spires darting into the heavens, and 3,140-plus statues, reportedly the most in any building anywhere. Milanese say that if you were to stack the statues, they would rise 3.3 miles.

You need not be so high to realize this: From the Duomo’s roof, the view carries the heavens.


Michael J. Bailey can be reached at michael.bailey@globe.com.