Top 10: Italian Cities

This is not an original concept, I admit. Guilty as charged. I’d like to think I’m making up for it though with a top 10 which is significantly different from the hundreds of similar lists. I’ve mainly avoided overly touristy cities not because I’m an Italy-hipster (although I probably am) but because getting ripped off is among the things most guaranteed to reduce my enjoyment in a city. I also prefer smaller cities, and in fact the biggest city on my list is only the 23rd biggest in Italy (some of my choices aren’t technically cities at all). Entirely by chance, nine regions are represented in my Top 10, which is very pleasing. So here, without further ado, are my top 10 cities in Italy (plus a few honourable mentions):

10) Aosta [Val d’Aosta]

This is an Italian city that’s been on a gap year to France and now tells everyone about it at every opportunity. It’s everywhere; in the architecture, the language and the traditions. A city so small it barely counts as one, but nonetheless the capital of the Val D’Aosta region.

Not to be Missed – On a sunny day, take a 15 minute drive out to Monte Bianco, Europe’s highest peak (avoiding the extortionate toll road with the only marginally slower regional road), and take the brand new Skyway cabin up to 3,400m. At that altitude, it is breath-taking in every sense of the word.

Val d'Aosta 

9) Orvieto [Umbria]

A former papal palace, perched perilously on a plateau (yay alliteration!) near the tri-border point with Lazio and Tuscany.

Not to be Missed – The houses in Orvieto were, in large part, built using rock taken from the same plateau on which they stand. A guided tour of a few of the estimated 600 underground caverns from which it was taken is fascinating.

[Edited from Peter Forster//Wikimedia Commons]

8) Padua [Veneto]

The city of Saint Anthony, Padova has a rich cultural, religious and gastronomic history, and the second most porticoes of any Italian city (after Bologna).

Not to be Missed – Difficult to pick just one thing, but Prato della Valle (pictured below), one of the largest piazzas in the world, is a beauty, especially on a sunny afternoon. Also, not even many Padovani know this, but the Abbazia di Santa Giustina (pictured in the background) is the resting place of St Luke (of Matthew, Mark, LUKE and John fame)



7) Trieste [Friuli-Venezia Giulia]

If Trieste were a person, it would have more passports than it is legal to own, with its Austro-Hungarian ancestry, one foot in Slovenia and large-scale Fascist-era Italian investment. This has undoubtedly prompted its incredible cultural history and blend of architectural styles.

Not to be Missed – Trieste was the site of the only death camp in Italy during WW2. Today, the Riseria San Sabbia is a memorial to the atrocities committed there, and it serves as a necessary reminder that Italy isn’t all sunshine and spritz, especially where its history is concerned.




6) Lucca [Tuscany]

A gem with everything that you’ve come to know and love about Tuscany, too often left in the shadow of the crooked tower ten minutes down the road in Pisa.

Not to be Missed – Go north, up to the Apuan Alps, and enjoy some dramatic mountain scenery in the heart of Tuscany, whether by foot or by car. Within Lucca itself, Piazza dell’Anfiteatro is hidden away, but worth seeking out.


5) Syracuse [Sicily]

Like the most successful tax evasion schemes, the historic centre of Syracuse is located off-shore. One of the most photogenic cities in Italy, finding an unattractive shot of it is almost impossible.

Not to be Missed – Syracuse used to be home to a sizeable Jewish community (around 5,000 at its peak). They were expelled under Spanish rule in 1492, but before leaving, they filled in the 6th century Jewish ritual bath (Mikveh) with dirt so that the Spanish wouldn’t desecrate it. It was uncovered by chance a mere few decades ago, and is now open to visitors. It is the oldest Mikveh discovered anywhere in Europe.


4) Bolzano [Trentino-Alto Adige/South Tyrol]

The architectural style, cleanliness and order of a particularly obsessive-compulsive German, with the friendliness of an Italian trying to sell you something, Bolzano is the best of two very different worlds.

Not to be Missed – Out of respect for your elders, go and visit Ötzi in the Bolzano Museum of Archaeology, because elders don’t get much older than the original iceman, who is over 5,000 years old. A short drive to the north, the Alpe di Siusi high-altitude meadow (pictured below) is the largest of its kind in Europe, with rolling green hills surrounded by typically dramatic Dolomite mountains at around 2,000m altitude.

Alpe de Siusi_Edited


3) Lecce [Puglia]

Nicknamed “The Florence of the South” owing to its baroque style, the second city of Puglia is unique in itself, and is surrounded by equally stunning nature.

Not to be Missed – take a day trip out to the coast, the Pugliese seaside is unrivalled. Of particular beauty is Santa Maria di Leuca, the south-eastern most point of Italy, and the meeting point of the Ionian and Adriatic Seas. The evening street performances in the central Piazza San Oronzo in Lecce during the summer lend themselves to a fun atmosphere.



2) Matera [Basilicata]

Much like myself first thing in the morning, Matera is really not photogenic. Unlike myself, going to Matera and seeing it “face-to-face” will make you realise just how stunning the European Capital of Culture 2019 actually is.

Not to be Missed – The Sassi cave dwellings, in which people have lived continuously for 9,000 years (the longest continuously inhabited place in Europe) are what makes Matera special, and many of them have been converted to serve the flourishing tourism industry.


1) Siena [Tuscany]

If you know me, you never had any doubt which city was going to be at number one. The city of the Palio, but so much more besides. Often done as a day trip from Florence, when really it should be the other way around.

Not to be Missed – Yes, the Palio is special, but if you don’t come at least a couple of days before and attend the pre-events, from the draw where the competing contradas are chosen, to the assigning of the horses, you’ll miss the sense of real civic importance which makes this event different from every other Palio/medieval re-enactment going in Italy. This is run by and for the Sienese themselves. The more you learn about the Palio and the history of alliances and rivalries between the 17 contradas (which continue to the present day), the more intriguing and incredible the whole event becomes.

Clockwise from Top Left: Torre del Mangia, Basilica of Saint Francis, panorama from near Piazza del Mercato. Photography is by the amazingly talented Maureen Berben.

Honourable mentions:

Mantova – An interesting city, which gets an honourable mention because of the Palazzo Te, and specifically the Sala dei Giganti therein. I’m not an artsy guy, so for me to say this was jaw-dropping is some indication of just how special it is. The more famous Palazzo Ducale is overrated, expensive and in a state of some disrepair.

Ravenna – The city itself is pretty, if not out-of-this-world stunning, but it gets an honourable mention for the remarkable mosaics, some over a thousand years old, in the main churches in the city.

Palermo – I would have Palermo fairly high up on the list itself, but I was constantly slightly on-edge when I visited and central parts of the city were really dilapidated, which isn’t ideal. The mix of architectural styles (often two or three within the same building) is unlike any other city I’ve ever visited, and even the dirt and grime can’t always stop the beauty of this city from coming through.

Pavia – A really lively city, close to Milan and infinitely more attractive, with much more to see. In particular, the Certosa di Pavia just to the north is the most incredible church/monastic complex I’ve ever seen.


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