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Chiara Rapaccini

61, between Via delle frasche and via Panisperna

I fell in love with Chiara Rapaccini. She's a woman, not a store, and this is her workshop – or “atelier,” as she prefers. A slim, elegant creature in her mid-50s, Chiara has the somewhat formal demeanour typical of natives of Florence, her home town. But don't be fooled. Her work – which includes paintings, sculptures, furniture and children's books – is whimsical, playful and a little bit weird. The almost-always exposed breasts of the female characters point straight up, with the nipples on top like cherries on an ice-cream scoop. Or there's an amusing green snake broken into five parts, each in its own frame. “I like fishes and snakes,” she says. Consider her place more gallery than store, though you are free to make offers on the unsold items. And she will do family portraits in the form of small wooden sculptures. Leave it to her imagination: You'll get something delightfully wacky – like the three sisters doing handstands on the back of a cow.

Da Valentino

37, At Vicolo dei Serpenti

The Valentini family, now led by patriarch Edmondo, 82, has been associated with this address since 1896. And things haven't changed much at the former beer hall. The building still has a “Peroni” sign painted over the entrance. The simple wood interior (including sadly primitive toilets) bears little hint of modern times. There's also not much variety on the menu. Pastas are rare and you can't get caffe. Come here instead for the house specialty: scamorze alla griglia. These are mozarella-type cheeses made from whole cow or buffalo milk. They're grilled, lightly bathed in olive oil and served with all manner of toppings. Mine comes sprinkled with walnuts. Sensational. Better yet, old Edmondo is always around to chat. “This is the real Rome,” he tells me. He has no intention to retire; his place is behind the bar.

Saint Louis College of Music

102/106, at Via Chimarra

Rome, I am told, has a thriving jazz and blues scene. You just have to know where to find it. This is a good place to start, since aspiring musicians and some of their best teachers get together in the warren of studios here – and, depending on what's happening, you can just stroll in and look at the art on the walls. If you're a visiting musician and feel like an impromptu lesson, the school is also happy to oblige. Several instructors, including Greg Burk, an American jazz pianist, speak English. Still, what Greg really loves is teaching Italians. “They're so enthusiastic,” he says. “They make much more noise than the American students.” As for the club scene? Should you grow weary of late-night opera in the Baths of Caracalla or church violin concertos, the staff will tell you about the best places in town and who's playing in them.

Tina Sondergaard

1D, between Via delle frasche and Via Panisperna

Tina Sondergaard is one of the many foreigners who came to Rome for a visit, got seduced by the city and never left. Now 46, the brassy Danish blonde has been here for decades doing a job she taught herself – clothing designer and tailor, or sartoria in Italian. She went to flea markets to buy used designer clothes, ripped them apart to see how they were constructed and then applied the knowledge to her own creations. The result is a mini fashion empire run from two shops. But she still makes clothes in the back of this store in Monti. And she says her skirts, dresses, hats and coats can all be worn to work, to a party or (how Italian) on a scooter. My wife bought a cute red party dress for $160 and Tina made sure it fit perfectly. Her other passion is Monti itself. Along with other activists, she's trying to limit traffic and promote art festivals on the tiny streets. “Monti is changing, but the change has got quality to it,” she says.

Macelleria Equina

141, between Via Chimarra and Via degli Zingari

The name engraved on the white marble slab over the shop door means “horse butcher shop.” And indeed it was, until at least the 1950s. But a decade later a young artist named Roberto di Jullo bought the tiny place for his art studio. Which was perfect since he loves horses – and not just on a Roman menu. At 62, he's one of the last original postwar artisans on via del Boschetto. He plays the part well with a handlebar mustache, dapper tweed clothes and memories of long-lost friends. As for the art itself: Women, hunting and horses inspire his paintings and drawings. The horses are galloping bundles of strength. “A lot of dead horses ended up in this shop,” he says. “This studio is their triumph.” Visit even if horse art is not your thing, though, since the interior – with grey marble walls and wooden ceilings from the 1700s – gives you a glimpse of old Monti.

Il Giardino del Te

112A, between Via Chimarra and Via degli Zingari

Do coffee-loving Romans drink tea? Carmen Marcat says they do and she's here to give converts choice, and lots of it. Her shop offers 150 varieties, all beautifully packaged and displayed. You can get Black Gunpowder from China, Formosa Oolong from Taiwan, Himalaya Royal from India and Malabar from Java. The prices for most are $8 per 100 grams, although some cost 10 times more. She also sells exotic sugars, salts and spices in a shop so sleek and airy it stands apart from the rest of the street. Carmen, 43, loves Monti. “It's still a very Roman neighbourhood,” she says. She just doesn't like the bureaucracy that smothers Italian shop owners. For years, she has been trying to get permits to open an outdoor tea garden to no avail. But the determined businesswoman is not giving up. Romans drink caffe outdoors. Soon, they will drink tea al fresco too.

Piazza La Bottega del Caffe

At Madonna dei Monti

The pretty square that runs off the lower end of Via del Boschetto – the Piazza Madonna dei Monti – is one of the few open spaces in this hilly, tightly packed neighbourhood. And it is a gem. The octagonal fountain, dating to 1589, seems to cool down the whole area. The lighting at night gives the buildings a subtle, soothing glow. Go to the far end of the piazza and peer left and you will see the fully intact side of the Colosseum in all its glory. There are several cafés and gelaterie here too. But we like the Bottega del Caffe. Not because it has the best coffees (most Roman coffee is good to superb), but because it has comfortable, cushioned seats and big canvas umbrellas to protect you from the sun. Enjoy.Eric Reguly is The Globe and Mail's European business correspondent, based in Rome.

In pictures: Via del Boschetto