What to do in Italy – The Classic, the Cool and the Weird

For years, Italy has been one of the most popular countries in Europe for tourists wanting a combination of beauty, history, culture, sun, beaches, and fabulous food and drink.

If you’ve never been… Well, go now. I mean it. It’s amazing. If you’ve already been and done the big sights, we’ve got some ideas for you too. And for those who want to see the more bizarre side of the country? Yep, got you covered as well. So here’s our Classic, Cool and Weird guide to Italy.

The Classics

Rome

Rome is chaotic, messy, noisy, full of life and soul, and a wonderful, wonderful place — Pexels cool weird classic Italy
Rome is chaotic, messy, noisy, full of life and soul, and a wonderful, wonderful place — Pexels

The Eternal City is still, no matter how exposed you’ve been to it on TV, on the internet or in books, a wonderful, wonderful place.

It’s chaotic, messy, noisy, full of life and soul, but is also the type of place where you can just as easily turn a corner and find yourself in a beautiful, quiet courtyard or backstreet that makes the madness seem like a distant memory.

Dodge the traffic and see the Colosseum; climb up to the Forum to be surrounded with weather- and time-beaten antiquities; go to the Vatican and climb up the inside of the vast dome of St. Peter’s Cathedral (the only place where I’ve ever felt vertiginous inside a building) and walk its long corridors of tapestries, maps and other assorted treasures; battle the hordes at the Trevi Fountain; or just simply sit at a table on some piazza or other, basking in the fact that you’re alive and at large in one of the world’s greatest cities.

Honestly, I’m jealous.

Venice

There’s no place like Venice in the world — Pixabay cool weird classic Italy
There’s no place in the world like Venice — Pixabay

In the words of Indiana Jones, ah, Venice. It can be unbearable in the summer, it has a recent history of ripping tourists off and it’s plagued by ship-loads of tourists who spill out onto the shore like ants, only to get in everyone’s way for two hours before being herded back on board… And yet, at its best, there’s nowhere like it in the world.

You can avoid the crowds if you avoid the obvious spots. St. Mark’s Square is the obvious one. Sure, go there to say you’ve been, but there are plenty more places to see.

The island of Burano is a higgledy-piggledy collection of brightly painted houses, or go to the Squero di San Trovaso to see if you can sneak a peek at the gondola repair yard that keeps Venice’s boats in tip-top shape.

The Malefatte Boutique is a serious oddity – a shop in which all the beautiful clothes have been made by prisoners – or you could head further afield to places like the wonderful San Francesco Della Vigna church (which is often empty even at the height of summer).

Of the surrounding places, the town of Chioggia is a similar but more laid-back proposition, and the island of Sant’Andrea is an overgrown delight in which the ruins of a 17th-century fort protrude through the undergrowth – a perfect spot for a picnic.

Florence

Countless galleries, fountains and public replicas of famous works will leave your lust for culture temporarily sated — Pexels Italy cool weird classic Italy
The countless galleries, fountains and public replicas of famous works in Florence will leave your lust for culture temporarily sated — Pexels

Slightly less hectic than Venice (not that that’s saying much), and equally impressive, Florence should be a highlight on any grand Italian tour. The cathedral is magnificent, the Ponte Vecchio mildly disappointing, but its main glory is the art.

The Uffizi Gallery is a marvel, and seeing Michelangelo’s glorious statue of David “in the flesh”, as it were, will leave you awestruck. Countless other galleries, fountains and public replicas of famous works will leave your lust for culture temporarily sated.

From Florence, you can also visit the charming city of Siena. Like a smaller version of Florence, its cathedral contains a mosaic that’s one of the largest and most ornate in Italy, covering the entire floorspace.

The main square, the Piazza del Campo, (which isn’t square by any means) is a gently sloping amphitheatre around which cafes and bars perch and, if you get bored of all that, the hills around make for beautiful walks with which to tire yourself out.

Milan

Milan is home to the largest Gothic cathedral on the planet — Pixabay Italy cool weird classic Italy
Milan is home to the largest Gothic cathedral on the planet — Pixabay

An elegant city, with less of the manic qualities of the more southern cities, Milan is, of course, fashion central.

Home to the largest Gothic cathedral on the planet (whose roof you can visit for stunning views all the way to the Alps on a clear day) as well as 20th century landmarks such as the oddly-loved Pirellone (the Pirelli Tower), and huge green spaces like the Sempione Park, you’ll have no problem feeling slightly aloof to have chosen so fine a city to visit.

Being this far north means Milanese cuisine is different from that which you’d typically get further south – rice instead of pasta, much fewer tomatoes and less fish, and more of a focus on red meat and stews.

Don’t imagine that just because it’s not what you’d think of as typical Italian fare that it’s not worth checking out; the city has over 150 Michelin-starred restaurants and around 20 bars and cafes registered as Historical Places of Italy, keeping their unique location, style and atmosphere untouched.

Sardinia

Surrounded by gorgeous beaches and with a mountainous interior, Sardinia is perfect for hiking and laying around  — Pixabay Italy cool weird classic Italy
Surrounded by gorgeous beaches and with a mountainous interior, Sardinia is perfect for hiking and laying around — Pixabay

If you’re not looking to spend time in a city, why not leave the mainland and head to beautiful Sardinia. Surrounded by gorgeous beaches and with a mountainous interior, it’s perfect for either hiking around in a sweaty, energetic way, or for lying back and doing basically nothing.

It’s very proudly slightly apart from the mainland, and one of the most obvious ways this manifests itself is in the language. Sardinian – and the other four languages spoken on the island – are a protected cultural artefact, and have “equal dignity”, to use the official phrase, with regular Italian.

Geologically and anthropologically, it’s one of the oldest places in Europe, and the island is dotted with prehistoric and neolithic sites, including temples, caves, standing stones and nuraghi, a type of tower-fortress.

Odd indeed to find Roman ruins that are more recent than basically all of the other points of archaeological interest on the island, but it is indeed so. When you’re done with exploring the island, you’ll want to at least visit Cagliari, the main city; a riot of colourful buildings seemingly sliding downhill towards the sea.

The Cool

Lecce and Gallipoli

Gallipoli is a small town connected to the mainland by a bridge built in the 16th century — Pixabay Italy cool weird classic Italy
Gallipoli is a small island town connected to the mainland by a bridge built in the 16th century — Pixabay

All the way down in the heel of Italy’s boot, south of the city of Brindisi, Lecce is difficult to get to, and this might be why few people make the effort. More fool them. It’s a grand place, a cultured mix of Roman and Baroque, simultaneously compact and striking.

It seems almost to glow, a consequence of the soft, golden limestone used in many of its structures and sculptures. Being so far south, it has an affinity with Greek culture not found elsewhere in the country, and in some of the surrounding towns, a dialect called grika is still spoken.

It’s not a big place – it’s home to fewer than 100,000 people – but has a strong sense of itself, which comes over in everything from the language to the food.

Around Lecce, Brindisi to the north will connect you even further with Greece: literally, in this case, as it’s the main ferry link to the Ionian islands. Gallipoli, around the same distance to the south, is a small town, whose ancient centre is stuck out on a limestone island, connected to the mainland by a bridge built in the 16th century.

The maze of tiny streets that make up the Old Town are full to bursting with tiny trattorias, where freshly caught fish is served with local wine to locals, who count their blessings under clear blue Mediterranean skies.

Perugia

The capital of the region of Umbria is home to one of Italy’s oldest universities — Pixabay Italy cool weird classic Italy
Perugia, the capital of the region of Umbria, is home to one of Italy’s oldest universities — Pixabay

Smack in the centre of the country, snaking along a ridge of hills and equidistant from Rome and Florence, Perugia is a quirky mix of the ancient and modern, from its ancient Etruscan roots to its insane modern public transport system (the MiniMetro).

The capital of the region of Umbria, it’s home to one of Italy’s oldest universities – as well as a number more – and is one of the cultural and artistic hubs of the nation.

Make sure you’re got strong legs as there’s seemingly always a hill to be dealt with, although this minor inconvenience is a fine trade-off for always having a view of the city from an interesting angle; in more than one case, from underground!

Part of the city is built underground, actually into the hills on which it stands. And this is no quirk for tourists, it’s a fully-functioning piece of infrastructure to this day, hosting markets, craft fairs and other events throughout the year.

Bologna

Bologna is becoming a place where young people are moving away from the homeliness, conservatism and cooking of their parents’ houses — Unsplash cool weird classic Italy
Bologna is becoming a place where young people are moving away from the homeliness, conservatism and cooking of their parents’ houses — Unsplash

 Bologna, as every quiz-lover knows, is home to the oldest university in the world, founded in 1088. It’s still going strong to this day, and it helps the city to become what it is; namely, something a little bit unusual in Italy.

It’s becoming a place where young people – possibly influenced by a number of students from other countries – are moving away from the homeliness, conservatism and cooking of their parents’ house and becoming brave enough to strike out on their own, adopting less typically Italian values.

LGBQT culture is generally more widely accepted in Bologna than elsewhere in the country, and the alternative art and music scene has a firm foothold. Music is used as a tool to fight racism and to promote equality and peace.

This is a good thing. Away from the student scene, Bologna has been famed for centuries as a place where some of the greatest and grandest spectacles of classical music, opera and ballet have been performed. Gioachino Rossini made it his home.

Even by Italian standards, the historical elements of the city are plentiful and well-maintained. In a far-sighted moment of genius, while other cities were using the 1970s to build awful, concrete tower blocks and suchlike, Bologna moved into a bold programme of restoration, cleaning, conservation and general make-good-ery of which its million or so people are rightfully proud of to this day.

Catania

Catania is not very touristy, which means you don’t feel as if you’re an inconvenience to locals — Pixabay Italy cool weird classic Italy
Catania is not very touristy, which means you don’t feel as if you’re an inconvenience to locals — Pixabay

Sicily’s second city lies in the shadow of Mount Etna, its streets paved with black, volcanic rock which, on the hottest days, seems to almost sizzle underfoot. Not necessarily the most attractive city when compared to the glories of Florence, let’s say, but an eminently liveable one.

It’s not very touristy, which means you don’t feel as if you’re an inconvenience to locals, who’ll barely even notice you in between zipping about on scooters, lounging in doorways and eating granita.

You could easily use Catania as a base to visit the surrounding towns of Siracusa (around an hour away) or Taormina (ditto), or, if you’re feeling adventurous, there’s a variety of hikes up and around Etna. Either that, or go to the beach! For a longer piece on Catania, have a read of this.

Genoa

Genoa is “stately”, “refined”, “imposing”, even “distinguished”— Pixabay Italy cool weird classic Italy
Genoa is stately, refined, imposing, even distinguished — Pixabay

Any city nicknamed la Superba has a lot to live up to, and Genoa certainly delivers in spades. Despite this, it’s never really considered a destination, as such, which is odd, because if Milan – a city equally based on trade and industry – is, why is Genoa overlooked?

Well, it’s not “pretty”, and I mean that in the nicest possible way. Better adjectives would be “stately”, “refined”, “imposing”, even “distinguished”. It has boulevards instead of Perugia’s alleyways; designer shirts rather than Catania’s scruffy jeans.

Not that this means it isn’t fun, mind you. The old harbour is wonderful and has sprouted some idiosyncratic sculpture to contrast with the replica of the galleon Neptune that’s moored there.

It takes its sport very seriously, and despite the passion, people feel for one of its two football teams – Genoa and Sampdoria – it’s one of the more friendly, piss-takey rivalries in Italian football; less die-for-the-cause, more laugh-at-your-neighbour.

For something a bit more elegant, take a stroll through one of the many parks, or take the evening air by promenading along the Corso Italia, overlooking the sea and the famous resort of Portofino beyond.

The Weird

Ultras from the other side

Livorno is one of the few clubs at which red stars, images of Che Guevara and hammer and sickle banners are prominently displayed— Pixabay Italy cool weird classic Italy
As well as the football, Livorno is an excellent place to catch a cruise ship — Pixabay

The city of Livorno has a history of being… contrary, let’s say. When the port was constructed near Pisa by the Medici family in the 15th century, a law known as the Leggi Livornine was passed, making Livorno the only Republic in which merchants of any nation were free to colonise.

500 years of this melting-pot came to a head with industrialisation, politicisation and, in 1921, the formation of the Italian Communist Party. The die was cast, and nowhere is this more obvious than at football games.

Often a place to show your political sympathies, Livorno is one of the few clubs at which red stars, images of Che Guevara and hammer and sickle banners are prominently displayed. The atmosphere can be intimidating – especially when playing, ahem, ideologically opposed clubs such as Lazio and Hellas Verona – but there’s nowhere else quite like it in the world of il Calcio.

Valley of the Mills, Sorrento

The valley is now home to the lush greenery that’s slowly eating into the huge stone factory complex— Dennis Jarvis / Flickr Italy cool weird classic Italy
The valley is now home to the lush greenery that’s slowly eating into the huge stone factory complex— Dennis Jarvis / Flickr

Located in… well, in a valley in Sorrento across the bay from Naples, lies a collection of buildings that were abandoned at the beginning of the 20th century. The valley itself is more of a crevasse; a huge rip in the earth, apparently created by an earthquake around 35,000 years ago, which is now home to the lush greenery that’s slowly eating into the huge stone factory complex.

The buildings themselves date back as far as the 13th century and, rather than giving you a view of city life, as you’d get by wandering around the ruins in Rome or the well-maintained streets of Siena, here’s a look at how rural life would have been, and now, a look at a world which humans have deserted.

Festivals

Over 800,000 people come to see the Buskers Festival in Ferrara over 11 days in August— Josefine b / Wikimedia Commons Italy cool weird classic Italy
Over 800,000 people come to see the Buskers Festival in Ferrara which runs for 11 days in August — Josefine b / Wikimedia Commons

Carpino Folk Festival is a very multi-generational festival in this small town of 5,000 people, where folk stories and songs are shared while the red wine flows.

A bigger and more lively offering happens in Ferrara, where the International Buskers Festival welcomes over 800,000 people over 11 days in August, with around 130 performances per day by street musicians from around the world.

A sagre is a festival derived from a local product and, throughout the harvest season, villages in Piedmont and Umbria will have truffle festivals, Umbria celebrates the humble chestnut, while Puglia does the same for olives. If that’s not enough, try Perugia’s International Chocolate Festival, one of the largest in Europe!

Ai Pioppi playground

Located in a forest driving north from Treviso, this bizarre adventure playground was originally conceived to promote a restaurant.

Over the last 40 years, it’s expanded and evolved, from the original giant slide down a hillside to include huge swings, merry-go-rounds, surreal-looking climbing frames and other things that are basically impossible to describe, all figments of one man’s imagination.

One of them involves a cannon. That’s all I know.

The Road of 52 Tunnels

To the north of Verona and Venice is a four mile long path that was originally built as a supply line to aid Italian soldiers fighting in the mountains against Austro-Hungarian forces, but due to the nature of the terrain – and the fact that, as is probably fairly obvious, 52 tunnels had to be dug through hillsides – it was also used as protection and hiding places during some of the fierce fightings.

The entire trail was constructed in under a year, which is phenomenal going, and can now be hiked. Four miles might not seem like a lot, but it’s not easy.

The paths can be narrow, mist rolls in and away suddenly, and none of the tunnels are lit, which means you’ll have to bring your own torch. Oh, and watch out for tunnel number 20, which is actually an upwards corkscrew. Good luck…!