There is a particular kind of disorientation that only Italy produces. You turn a corner in Rome searching for a café and find yourself standing in front of a 2,000-year-old temple that has been in continuous use since the reign of Augustus. In Naples you order pizza and end up in a three-hour conversation with the baker's grandfather about the correct temperature of a wood-fired oven. In the countryside, somewhere between one hill town and the next, you realise you've been driving for twenty minutes without looking at your phone and feel, briefly, like a different kind of person.
Italy does this. It pulls you out of whatever pace you arrived with and installs its own. The sooner you stop resisting, the better the trip becomes.
"Italy doesn't care how little time you have. It will take what it needs, and give back considerably more."
Rome operates on a scale that has no modern equivalent. Other cities have ancient ruins — Rome has an entire ancient city buried under, and woven through, a living modern one. The Pantheon sits in a piazza where people eat gelato and argue about football. The Forum is ten minutes' walk from designer boutiques. The Colosseum rises above a busy intersection like it simply couldn't be bothered to leave.
My first morning I did what you're supposed to do — arrived at the Colosseum before the gates opened, watched the sun clear the arches of the Forum, tried to hold 2,000 years of history in my head simultaneously, failed completely, and found the failure deeply pleasant. Rome exceeds comprehension. That's the point. You stop trying to understand it and start trying to feel it instead.
The Rome nobody talks about
The Vatican, the Colosseum, the Trevi Fountain — these are non-negotiable and worth every crowd you'll endure to see them. But the Rome that will stay with you is found in its neighbourhoods. Trastevere at dusk, when the golden light bounces off ochre walls and the restaurants set up tables in cobblestone lanes. Testaccio, the old slaughterhouse district turned food quarter, where the market opens at dawn and the cacio e pepe at Da Remo is as good as any you'll eat anywhere. Pigneto, east of the centre, where young Romans actually live — vinyl record shops, natural wine bars, one extraordinary arancino from a counter that's been there since 1961.
Rome — the essentials
Book the Colosseum online — the queue without a ticket can run three hours. With one, you walk straight in. The Forum and Palatine Hill are included in the same ticket and are, if anything, more affecting than the arena itself.
The Vatican Museums require a separate ticket, also bookable online. The Sistine Chapel is the destination everyone mentions. The Gallery of Maps, a long corridor painted floor to ceiling with 40 topographical maps of 16th-century Italy, is the one people remember.
Eat where there is no English menu. If the restaurant has photographs of the food outside, keep walking. Find somewhere with a handwritten specials board and a proprietor who looks mildly suspicious of you. Order whatever they recommend.
Walk everywhere in the historic centre. Rome's greatest pleasure is what you find between destinations — a courtyard, a fountain, a church door left open revealing candlelight within.
How long: Three nights minimum. Four is better. Rome resists rushing and rewards staying.
"You stop trying to understand Rome and start trying to feel it instead. That's when the city opens."
The best single hour I spent in Rome was at the Borghese Gallery — a villa in the park above the city housing one of the great private art collections in Europe, including Bernini sculptures of such impossible beauty that several times I found myself checking whether the marble was actually marble. Visits are timed and ticketed to strict limits of two hours and 360 people. Book weeks in advance. It is worth any inconvenience required to get inside.
Naples will unsettle you before it seduces you. The train pulls in and the city hits immediately — loud, layered, slightly overwhelming, nothing like what you expected. The centro storico is a UNESCO World Heritage Site that nobody told was supposed to behave like one. Laundry hangs between apartment windows six storeys above streets barely wide enough for a single car. Shrines to Maradona share wall space with shrines to the Madonna. Every surface is covered in something.
Give it two hours. By the third, you'll have forgotten every hesitation.
Pizza. Obviously.
Neapolitan pizza is not a variation of pizza. It is the original, and everything else — every thick-crust, every sourdough, every wood-fired artisan interpretation in every city in the world — is a response to it. The dough ferments for at least 24 hours. The tomatoes are San Marzano, grown in volcanic soil south of Vesuvius. The mozzarella is fior di latte or buffalo, made the same morning. The oven runs at 485°C. The pizza cooks in 60 to 90 seconds.
You eat it standing up, or at a small table with no reservation, with a cold Peroni and no particular agenda. It costs perhaps €5. It is one of the greatest things you will ever put in your mouth.
Naples — where to eat, what to know
Pizza: The debate between L'Antica Pizzeria da Michele (founded 1870, two options on the menu — Margherita or Marinara, cash only, line out the door) and Sorbillo on Via dei Tribunali is the Naples version of a local religion. Go to both. Form your own view. It will be wrong to half of Naples regardless.
Sfogliatella — a ridged, shell-shaped pastry filled with ricotta and candied citrus — from Pintauro on Via Toledo, open since 1785. Get there when they come out of the oven. There are two versions: sfogliatella riccia (flaky, layered) and frolla (short pastry). The riccia is superior. This is not a debate.
The National Archaeological Museum houses the greatest collection of Roman-era art in existence — everything excavated from Pompeii and Herculaneum. Allow a full morning. The Secret Cabinet (erotic art from Pompeii, now publicly accessible) is genuinely fascinating.
Safety: Naples has a reputation that precedes it and largely doesn't deserve it. Stay aware in the centro storico as you would in any dense city, keep your bag in front of you on busy streets, and don't let mild urban paranoia prevent you from exploring freely. The city rewards those who engage with it.
Day trip: Pompeii is 30 minutes by circumvesuviana train. Go. Walk the streets of a city frozen in 79AD and understand, in a way no museum can replicate, that people 2,000 years ago had kitchens, arguments, favourite restaurants, and graffiti on the walls.
"Naples is the kind of city that asks something of you. Come with an open mind, comfortable shoes, and an appetite for controlled chaos. It will give back everything you offer and then some."
The Spanish Quarters — the dense grid of narrow streets west of Via Toledo — are where Naples becomes entirely itself. Here the street life is overwhelming and wonderful in equal measure. Children play between parked Vespas. Elderly women conduct conversations between windows three floors apart. The smell of frying dough and espresso drifts from doorways. Everything feels like it has been exactly this way for a long time, and probably has.
Between Rome and Naples lies a landscape most visitors see only from a train window, and almost none stop to explore. This is a significant mistake. The Italian countryside — rolling hills, medieval hilltop towns, vineyards running to the horizon, narrow roads through olive groves that have been productive since before the Roman Empire — is where Italy stops performing for visitors and simply exists for itself.
Rent a car. This is non-negotiable. The countryside cannot be understood from a train or a tour bus. It must be driven, slowly, with no particular schedule, through towns you've never heard of, stopping when something looks interesting, which will be constantly.
Campania and the hills above Naples
The region surrounding Naples — Campania — is among the most fertile and beautiful in Europe. The Amalfi Coast gets the photographs, and it deserves them, but the inland hill towns above it are where you find the version of southern Italy that hasn't been arranged for anyone's benefit. Ravello sits above the coast on a promontory with views that justify every hairpin bend on the road up. Sant'Agata sui Due Golfi, a tiny village between the bays of Naples and Salerno, has a restaurant, Don Alfonso 1890, that has been holding two Michelin stars for decades and remains one of the great meals in Italy.
Driving in Italy — what you need to know
ZTL zones (Zona Traffico Limitato) exist in the historic centres of most Italian cities and many towns. Driving into one without a permit will result in a fine that arrives by post months later. Check maps carefully before driving into any walled town centre.
Autostrada (motorways) are excellent, fast, and toll-based. Keep a card handy — many toll booths are now card-only.
SS roads — the smaller state roads — are where the countryside reveals itself. Slower, sometimes narrow, occasionally alarming on mountain sections, always more interesting than the motorway.
Book accommodation with parking confirmed in advance, particularly in hilltop towns where streets are medieval in width.
International Driving Permit: Canadian licence holders should carry an IDP alongside their licence when driving in Italy. Obtain one through CAA before departing.
Lazio — the hills around Rome
Within an hour of Rome lies a landscape almost no tourist visits. The Castelli Romani — a chain of hilltop towns in the Alban Hills southeast of the city — produce excellent white wine, have been weekend retreats for Romans since the days of the Republic, and contain some of the most quietly beautiful piazzas in Italy. Frascati, Castel Gandolfo perched above its volcanic lake, Nemi famous for its strawberries — these are places where Romans go to eat and drink and remember that their city, magnificent as it is, is not the whole world.
"The countryside is where Italy stops performing and simply exists. That, it turns out, is when it becomes most beautiful."
I spent a night in Viterbo, a walled medieval city two hours north of Rome that sees a fraction of the visitors it deserves. The centro storico is entirely intact — walking it after dark, the stone streets empty and lit by lanterns, the medieval towers rising against a clear sky full of stars, I felt further from the 21st century than I have anywhere in Europe. The restaurant I found by accident served pasta with local truffles and a carafe of rough local wine, and the bill was €18. The proprietor pressed a small bottle of olive oil into my hand as I left.
This is what the Italian countryside does. It surprises you with generosity when you've stopped expecting it. It rewards slowness with experiences that no amount of planning could replicate. It asks you, quietly but firmly, to reconsider the pace at which you ordinarily move through the world.
How to structure an Italy trip
The temptation with Italy is to do too much — Rome, Florence, Venice, the Amalfi Coast, Milan, all in ten days. Resist this entirely. Italy punishes rushing and rewards depth. A week split between Rome and Naples with two days of driving in between will leave you with more of Italy than a two-week blur of train connections ever could.
A suggested 8-day itinerary
Days 1–3 · Rome. Colosseum and Forum on day one. Vatican on day two (book the Borghese Gallery for the afternoon). Day three belongs to the neighbourhoods — Trastevere, Testaccio, the Aventine Hill at sunset.
Day 4 · Drive south. Rome to Naples via the Castelli Romani and the Via Appia Antica — the ancient road south, flanked by umbrella pines and dotted with Roman tombs. Stop in Terracina for lunch by the sea.
Days 5–6 · Naples. Day one: the centro storico, the Archaeological Museum, pizza at lunch and dinner without apology. Day two: Pompeii in the morning, return for aperitivo in the Spanish Quarters at dusk.
Day 7 · The Amalfi Coast or Cilento. Drive the coast road from Naples to Positano and Ravello for the drama, or head south to the Cilento — wilder, quieter, less photographed, equally beautiful.
Day 8 · Return. Naples to Rome by high-speed train takes just over an hour. Spend the afternoon back in Rome, revisit your favourite piazza, and don't try to fit anything else in.
On my last evening in Italy I sat in a piazza in a hill town whose name I've since struggled to find on a map — somewhere in the hills east of Naples, a place of perhaps 800 people, a church, a bar, and a view across the valley to Vesuvius on the horizon. An old man played accordion at a table outside the bar. Three generations of one family occupied the table next to mine, talking over each other in the way Italian families do, the youngest perhaps three years old, the oldest well past eighty.
The wine was local, cheap, and perfect. The accordion played something I didn't recognise. Vesuvius sat dark and enormous in the last light, and I thought about the 79AD eruption and the cities it buried and the 1,900 years of vineyards that have grown in its volcanic soil since then, and about how Italy has this way of making history feel less like the past and more like something that simply keeps happening, all around you, all the time.
Come for a week. Come back for longer. You will — everyone does.
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