Italy’s most overrated and underrated destinations

Italy’s most overrated and underrated destinations
Urbino: over or underrated? Photo: DepositPhotos

In a country as often visited as Italy, there are bound to be some tourist traps – as well some hidden gems that get past the guidebooks. American writer John Henderson gives his list of which destinations to skip and which to seek out.


What doesn’t the average traveller know about my adopted country? A lot. Italy isn’t all quiet canals, Dolomites and cappuccini in dreamy piazzas, ancient islands in an azure sea and endless vineyards in the Tuscan countryside.

It has its sore spots. It doesn’t have many. I struggled to find five overrated places in Italy. But they are there and as you all plan vacations for 2019, here’s a tip sheet: Italy’s most overrated and underrated destinations.

I’ve been to all of them. Use it as a warning; use it as an insider’s tip. But use it. And feel free to weigh in with your thoughts. (Those threatening my life please form a line to the right.)

Most overrated

1. Milan

Photo: Miguel Medina/AFP

It’s Newark with a big church. The Duomo is worth a visit. The white facade with 135 spires looks like a birthday cake. But once you get past that, Milan visually pales compared to other Italian cities. Don’t blame the Milanese. It’s not their fault Allied forces bombed the place back to the Stone Age in World War II. But what’s built in its place is too modern to look historical, too old to look clean.

The weather is usually awful. Yes, you can see the Alps from there — on July 15th, about the only day there’s good enough weather to see past architecture as dull as Milanese cuisine. When your headlining dish is osso buco, a sloppy veal stew, you don’t deserve to be called Italian. Plus, their soccer teams suck. (Forza Roma!)

2. Cortona

Photo: RobertoEncini/DepositPhotos

Ever read Under the Tuscan Sun? If you didn’t, you’ve never wanted to visit Italy or don’t like self-obsessed chick lit.

It’s about a woman building a new life in a fixer-upper in Tuscany, interspersed with Italian recipes. The 1996 blockbuster made Cortona, where author Frances Mayes lived, a must stop on the American tourist’s beaten path in Italy. Americans walk around town carrying her book, trying to identify her butcher, her vegetable stand and florist. Cortonese told me they felt like zoo animals.

The truth is, Italy has dozens of quaint, walled cities like Cortona. You don’t need to fight tour buses to see one.

3. Trieste

Photo: Giuseppe Cacace/AFP

It figures that James Joyce would live in a town like Trieste for ten years. I disliked them both. It’s a good debate which one is more boring.

Trieste has the biggest seaside piazza in the world. Maybe that’s because there aren’t many. Piazza dell’Unita d’Italia is a massive 130,000-square-foot expanse weighed down like anchors by grey government buildings and two overpriced cafés. There is no brilliant architectural treasure as you’d find in lesser-known piazzas such as Palazzo Re Enzo in Bologna’s Piazza del Nettuno or Palazzo dei Capitani del Popolo in Ascoli Piceno’s Piazza del Popolo.

Also, tucked into Italy’s northeast corner on the north end of the Adriatic, Trieste is constantly plagued by the Bora, the cold wind that sweeps down from the hills surrounding the town.

4. Capri

Photo: Daniel Slim/AFP

Come here if you want to see or be seen — or stand in line for 30 minutes waiting for a bus to take you zigzagging up the hill. Granted, the hill’s view down to the Tyrrhenian Sea is one of the best in Europe. It’s a lot better than the views of elbows and asses that squeeze past you in the impossibly crowded Piazza Umberto I.

While the island is beautiful and the sea is inviting, Capri has no beach. None. At one spot I had to pay €21 to lay a towel on a rock. Without €500 loafers and a €300 sweater wrapped strategically around my shoulders I felt like Oliver Twist scavenging for more gruel.

5. Costa Smeralda 

Photo: gevision/DepositPhotos

See above but spread it out for 55 kilometres across the north-east corner of Sardinia, without Capri’s views.

Costa Smeralda is the epicentre for Italians’ August exodus. It’s lined with stuffy hotels, private marinas and tricked-out yachts. Beautiful, tanned Italians with sunglasses that cost more than their weekly food budget sit on yachts and drink spritz and wine on the bows of beautiful boats.

It’s the height of Italian stuffiness and a magnet for Italians wanting to join the A-list celebs for a glass of Campari. Porto Cervo, Costa Smeralda’s main town, is as phoney as an ageing Italian actress’ face. And the prices in August make you wonder if Italy invented price gouging.

Most underrated

1. Procida

Photo: mikolajn/Depositphotos

I’ve written about this idyllic little island before and I will the rest of my life. It’s right out of a movie set — which it was in 1994 when it was the setting for Il Postino, the classic love story about a postman in 1950s Italy who falls in love with a fellow islander.

You can relive old Italy here. Just sit on one of the dockside restaurants with a Neapolitan pizza or dine at the heart-throbbingly romantic La Lampara above the idyllic harbour and fall in love all over again. Then the next day go to the white sand beach on the north side of the island.

Procida is only ten miles north of Capri but a million miles away in authenticity.

2. Turin

Photo: Giuseppe Cacace/AFP

Italians used to call Turin the Detroit of Italy. These Italians have never been to Detroit. The only thing Turin and Detroit have in common is car manufacturing, except the cars out of Turin actually work.

Turin, the gateway to the Italian Alps, is speckled with beautiful piazzas, tree-lined boulevards and long porticoed walkways. The 2006 Winter Olympics gave it a bit of a facelift but two things I love here stayed the same: the Mole, the spired museum dedicated to Italian film, and Barolo, Italy’s best wine and my favourite in the world.

3. Castelli Romani 

Ariccia. Photo: sislavio/Depositphotos

One of Rome’s best secrets, Castelli Romani is a series of 14 small towns, many sporting castles, in the Alban Hills southeast of Rome.

Each one has its own distinct draw, like gelato has different flavours: Ariccia for porchetta, the sizzling roast pork eaten at a string of outdoor restaurants; Nemi, on the beautiful volcanic Lago di Nemi, home to great views and some of the best strawberries in the world; Genzano, where many wealthy Romans lived during Ancient Rome and now where Romans go for the best bread around; Castel Gandolfo, on Lago di Albano, so beautiful you’ll see why the popes have their summer residence here; Frascati, blessed with a beautiful park, perfect for a picnic with the town’s trademark refreshing white wine.

4. Arcipelago di La Maddalena

Photo: Daniel Slim/AFP

If you see Costa Smeralda, keep right on going to the point town of Palau and take the 15-minute boat ride to Maddalena. It’s a national park consisting of seven small islands all lined with gorgeous white sand beaches on romantic, individually carved bays.

Don’t let the US naval base scare you. The personnel are well behaved and blend in with the kind locals. You need a car and a camera. You’ll want to stop around every curve for a photo.

5. Urbino

Photo: w20er/DepositPhotos

I call Le Marche "Tuscany Light". Le Marche has everything its more famous neighbour has but with a third the tourists and cheaper prices.

Urbino is the jewel of Le Marche. High atop a hill, the walled city of 15,000 people is so beautiful Unesco made it a World Heritage Site in 1998. The home of the great Renaissance artist Raphael has kept its artsy rep after 600 years.

Eat Le Marche’s signature strozzapreti ('priest strangler') pasta in the dimly lit Palazzo Ducale or just settle in with a glass of Le Marche’s trademark Verdicchio white wine.


John Henderson is a writer and expat living in Rome. This is an edited version of an article that was originally published on his blog, Dog-Eared Passport. Find more of his travel stories here.

Want to write a guest blog for The Local Italy? Get in touch at [email protected].



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