I have been leading food and wine groups through Italy for the better part of a decade, and before that I cooked in Lyon and ate my way through Piedmont and Tuscany on my days off. Italy is the country I know best after my own. It is also the country where I watch the most avoidable mistakes turn good trips into expensive ones.
Here is what I tell friends. Take what is useful.
1. Five Days Is Not Three Cities
Rome, Florence, Venice in five days. I hear this plan every week and I always say the same thing. Pick one.
You will spend your trip wheeling a suitcase through Roma Termini and standing in line at the Frecciarossa ticket machine. Rome wants three days minimum. Florence wants two or three. Venice wants two. That is eight days before you have set foot in a single trattoria with intention.
The best afternoons I have had in Italy were the ones with nothing on the schedule. A long lunch at Da Cesare al Casaletto in Rome that turned into four hours because the owner kept opening bottles. A walk through Testaccio that ended at a butcher who sliced me a piece of guanciale to chew on the way out. You cannot plan that. You can leave room for it.
2. Where You Sleep Decides How You Eat
First-time visitors book near the train station because the map looks convenient. The neighborhoods around Roma Termini, Milano Centrale, and Firenze Santa Maria Novella are the worst food in each city by a wide margin. Tourist menus in four languages, frozen carbonara, the works.
Stay in Trastevere, Monti, or the streets behind the Pantheon in Rome. In Florence, cross the river to Oltrarno where Il Santo Bevitore and Trattoria Cammillo are within a fifteen-minute walk of each other. In Naples, the Centro Storico puts you ten minutes from Concettina ai Tre Santi for pizza and L’Ebbrezza di Noè for natural wine. In Milan, Brera or Navigli.
The train station is a place you walk through with a coffee. It is not a place you wake up.
3. Book the Big Stuff Before You Get on the Plane
The Galleria Borghese is reservation only. Not on weekends, not in summer, always. People show up at the door and get turned away every single day. The Last Supper in Milan sells out four to six weeks ahead.
The Vatican Museums without a pre-booked ticket means a queue that takes two or three hours of your morning. The Colosseum runs on timed entry now. The Uffizi and the Accademia will eat half a day in line if you walk up.
Book direct on the official sites months ahead. Bring the photo ID that matches the name on the ticket because they check it now.
4. Italian Museums Close on Mondays
Most of them, anyway. The Uffizi, the Borghese, the Accademia, large sections of the Vatican Museums. I have watched people walk across Florence in July heat to find a locked gate.
Use Monday for the things that stay open. Churches are almost always free and operating, and the Brancacci Chapel and Santa Maria Novella in Florence are worth a whole morning between them. Markets run. Mercato Centrale, Mercato di Testaccio, the Rialto fish market in Venice if you get there by 9am. Food tours run. Use the day.
5. The Fish Menu Scam That Still Works
Fresh fish in Italian restaurants is priced all’etto, meaning per 100 grams. You see “branzino, 8 euro” and assume your plate costs 8 euros. The fish weighs 500 grams. Your plate now costs 40 euros, and that is before the contorno, the wine, the coperto, and your friend’s identical fish.
This made the international news again last year when two tourists got hit for 410 euros for two whole fish, some spaghetti, and water near the Trevi. The restaurant did nothing illegal. The customers did not ask.
When you see all’etto, /etto, or al kg, ask the waiter to bring the fish to the table before cooking and tell you the total. “Quanto costa il pesce, tutto compreso?” Any reputable place does this without flinching. The ones that resist are telling you something.
6. Two Numbers That Save You Real Money
Fixed taxi fares from the airports. Fiumicino to inside the Aurelian walls is 50 euros, Ciampino is 31, Malpensa to central Milan is 105. These include luggage, all passengers, and tolls. Before the driver pulls away, say “tariffa fissa” and state the amount. Get out if he tells you it does not apply.
Second, the ATMs in airports and tourist piazzas. The ones branded Euronet, Travelex, and YourCash are not banks. They are private currency conversion machines designed to take 25 to 35 euros out of every 300 you withdraw through something called dynamic currency conversion.
Use Intesa Sanpaolo, UniCredit, or BNL. When the screen asks if you want to be charged in your home currency, always choose euros.
7. Check Which Airport the Cheap Flight Actually Lands In
Ryanair’s Milan is usually Bergamo, an hour out by bus. Their Venice is sometimes Treviso, also an hour out with worse connections. Their Rome can be Ciampino, which is fine but not Fiumicino.
By the time you add the shuttle, the time, and a taxi at the other end, the budget flight often costs more than a direct one. Read the airport code, not the city name.
8. The ZTL Will Cost You More Than Your Hotel
ZTL means Zona Traffico Limitato, the restricted traffic zone in every Italian historic center. Cameras read your plate the moment you cross in. The fine generates automatically. You find out four months later when a letter arrives at home, or when your rental company quietly charges your card.
Fines run 80 to 335 euros per camera, per entry. Drive a loop around a piazza looking for parking and you can trigger three of them in five minutes. The rental company tacks on a 40 euro administrative fee per ticket for the privilege of giving the authorities your name.
Google Maps does not warn you. The signs exist but they are small, high on a wall, and abbreviated. My rule is firm. Rental car and historic city center do not mix. Park outside the walls and walk in, or take a bus. If your hotel sits inside a ZTL, call them before you arrive and ask them to register your plate. Most can.
9. Do Not Drive the Amalfi Coast
The SS163 is a two-lane road cut into a cliff face. It is not wide enough for two cars in many sections, the buses do not slow down, and there are stretches with no guardrail. A 30 kilometer drive in August takes two and a half hours, and parking in Positano runs 8 euros an hour with no spots after 10am.
Take the ferry. Sorrento, Positano, Amalfi, Salerno, all connected, all running through the season, and the coast looks better from the water than from a windshield. The SITA bus also works if you can handle the switchbacks. Save the rental for Puglia or the Maremma where the roads are made for it.
10. The Italian Word You Need Is Sciopero
Italy runs one or two scheduled transport strikes a month. They are announced in Italian on government websites that nobody outside Italy reads. Sciopero means strike. Learn it.
In February a national rail strike stranded tourists across four cities. Departure boards went solid red at Milano Centrale. People missed flights home. People ate non-refundable hotel nights in cities they had already checked out of.
Bookmark scioperi.mit.gov.it and check it the week of your trip. Most important rule, the one I will not budge on, if you have an international flight out, arrive in the departure city the night before. One extra hotel night is 100 euros. A missed long-haul flight rebooked at the counter is 800 to 2,000.
11. Venice Charges Day-Trippers Now
Since 2024, Venice charges a 5 euro access fee on roughly thirty peak days a year, mostly weekends from late April through mid-July. If you are visiting for the day without a hotel booking inside the lagoon, you register and pay online before you arrive.
The fine for not paying runs up to 300 euros. Overnight hotel guests are exempt, which is one more reason to sleep there. Venice empties out after the day-trippers leave around 6pm, and the city you see between 7pm and 10am is a different city.
12. Google Maps Does Not Work in Venice
When Google says 12 minutes, allow 40. The GPS calculates a straight line and Venice does not have straight lines. Alleys dead-end at canals. Bridges are not where they look. Streets named the same thing exist in three different sestieri.
Follow the painted yellow signs on the buildings. San Marco, Rialto, Ferrovia, Piazzale Roma. They have guided people through this city for longer than GPS has existed and they still work.
13. The Vests Outside the Colosseum
Outside the Colosseum, the Vatican, and Pompeii you will get approached by men and women in official-looking vests selling skip-the-line tours. Some are real operators. Many sell you the same timed-entry ticket the museum sells for triple the price, or worse, a ticket that does not actually exist.
Book the official site, or use Walks of Italy or Context Travel which are licensed operators with real guides. Anyone who walks up to you on the sidewalk is selling you something you do not need.
14. You Are Probably Overpaying for Tickets Right Now
Google “Colosseum tickets” and the first three results are resellers, not the official site. They outrank the real one because they spend more on ads. They charge 50 to 70 euros for an 18 euro ticket. The “skip the line priority access” they sell is the exact same timed-entry slot the official site sells. There is no separate fast lane.
Same story for the Uffizi, the Borghese, the Last Supper, and Pompeii. Always book direct. The official site for the Colosseum is colosseo.it. The Vatican is museivaticani.va. The Uffizi is uffizi.it. If a site is charging more than double face value, close the tab.
15. Skip August
Ferragosto on August 15th is the biggest national holiday in Italy and the surrounding three weeks are when most Italians take their break. Restaurants close. Real restaurants, the family-run trattorias that make the country what it is. Shops close. Whole blocks of Trastevere and Brera go dark.
What stays open in August is the tourist apparatus. The places with pictures of the food on the menu. It is also brutally hot, the coast is packed shoulder to shoulder, and prices peak.
May, June, September, and October are when Italy actually shows up for you. September is the best month I know. The vendemmia is happening across most of the wine regions, the light goes amber by 5pm, and the tourist volume drops the second the schools restart up north.
16. The Part That Matters
The trips people still talk about ten years later are not the ones where they saw the most. They are the ones where something happened in the gaps.
A long lunch at a place with paper tablecloths in Bologna where the owner sat down with you because the kitchen was quiet. The piazza in Lecce at 9pm where the old men argue about Roma versus Lazio and the women play cards with a half-empty bottle of Negroamaro.
The shopkeeper in Orvieto who tells you the church across the street has a Signorelli fresco cycle most tourists never see, because you asked one real question about the town.
Leave gaps. Leave whole days open. Walk without a destination. Say yes to the bottle the producer wants to open for you even though you were going to leave at four.
Italy happens between the monuments. Plan enough to get yourself there. Plan loosely enough that the country can do the rest.
