What I’d Do Differently: Italy Edition

Updated April 2026 | 9 min read

What I’d Do Differently: Italy Edition

I’ve been to Italy more times than I can justify on a budget — Rome, Naples, Capri, the Amalfi Coast, Positano, Ravello, Sorrento, Florence, Venice, Milan, Trieste, and a detour to Monza for the Formula 1 Grand Prix. I’ve made the classic mistakes, paid for them, and course-corrected. This post is what I wish someone had told me before the first trip, and what I remind myself before every one after.

This is part of the “What I’d Do Differently” series — one destination, one honest post about the lessons that cost time, money, or both.

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1. Book the Colosseum before anything else

Not before you book your hotels. Before you book your flights. The Colosseum timed-entry tickets sell out weeks in advance, and in peak season they’re gone the moment they go live. I booked flights, accommodation, and half my itinerary before I thought to check availability — and then spent two hours on a Tuesday morning frantically refreshing for cancellations.

Book at coopculture.it, which is the official ticketing platform. Not Viator, not GetYourGuide, not whatever ad shows up when you search “Colosseum tickets.” Those third-party platforms are fine in theory but they mark up the price and sometimes hold inventory that doesn’t actually exist until you try to exchange it at the gate.

The arena floor add-on — which puts you down on the actual floor where the gladiators stood — is worth every euro and sells out even faster than standard access. If it’s available when you’re booking, take it without deliberating.

2. Skip Positano for sleeping, not for seeing

Positano is genuinely beautiful. The stacked pastel buildings, the narrow staircases, the light in the late afternoon — it earns every photograph. I’m not telling you not to go. I’m telling you not to sleep there.

A mid-range hotel in Positano runs €250 to €400 per night in summer. A mid-range hotel in Sorrento costs €80 to €120. The ferry from Sorrento to Positano takes about 35 minutes. Go for four or five hours, walk down to the beach, eat lunch, take your photos, leave before dinner. The sunset from Sorrento’s old town is not €200 worse than the sunset from a Positano terrace you’re paying for. I promise.

Sorrento is a real town with real grocery stores, a functioning piazza, and restaurants where the menu isn’t laminated in English. It’s a much better base for the whole coast.

3. The Circumvesuviana is not the high-speed train

The Circumvesuviana is the regional train that runs from Naples Porta Nolana to Sorrento, stopping at Pompeii along the way. It is not the Frecciarossa. It is not the Italo. It is an old regional train that stops constantly, is almost always crowded, and occasionally has no air conditioning in the middle of August.

Budget 40 minutes to Pompeii, about 70 minutes to Sorrento from Naples. These times assume normal delays, which are common. Don’t try to time a tight connection off this train.

A few practical things: don’t stand near the doors, which is where pickpockets work. Keep your phone and wallet in front pockets, not a bag that’s behind you in a crowd. The train is perfectly fine — I’ve taken it a dozen times — it just requires the kind of alertness you’d apply to any busy commuter rail in a major city.

The ticket is a few euros. It’s one of the best-value rides in the country. Just know what you’re getting into.

4. Learn the four Roman pastas

Rome has four canonical pasta dishes: cacio e pepe, carbonara, amatriciana, and gricia. Every restaurant in the city serves at least one of them, and knowing what the correct version looks like is the difference between eating the real thing and paying €18 for a tourist-trap approximation.

Carbonara does not contain cream. It never has. It’s egg yolk, guanciale, Pecorino Romano, and black pepper — the creaminess comes from emulsification, not dairy. If you see cream listed in the description, walk out. Cacio e pepe is Pecorino, pasta water, and black pepper. That’s it. Gricia is the ancestor of both — guanciale and Pecorino, no egg. Amatriciana adds tomato.

For cacio e pepe specifically, Felice al Testaccio is not negotiable. It’s in Testaccio, which is a real neighborhood that Romans actually live in, and the pasta is made tableside in a wheel of aged cheese. Book ahead. Go for lunch if dinner is full.

5. Don’t rent a car on the Amalfi Coast

The SS163 — the Amalfi Drive — is a two-lane cliff road where the lanes are approximately the width of one European compact car. Buses take up both lanes on hairpin turns. Scooters pass in gaps that don’t exist. Parking in Amalfi or Ravello or anywhere on the coast is either nonexistent or costs more than your hotel per day.

The SITA bus runs the entire coast for €2.50 per leg. The ferry connects Sorrento, Positano, Amalfi, and Salerno and costs €8 to €15 depending on the route. Both are reliable in the sense that they run on a published schedule and the drivers know the road better than any tourist ever will.

If you are an experienced driver who has navigated mountain roads in Sicily or the Swiss Alps and finds that kind of driving relaxing, this disclaimer is not for you. For everyone else: the bus. The ferry. You will enjoy the coast more when you’re looking at the scenery instead of calculating whether the bus coming around the corner is going to clip your mirror.

6. Ravello is the best town on the Amalfi Coast

Nobody goes to Ravello because it’s not on the water. It sits up on the ridge, about 350 meters above sea level, overlooking everything. The tour groups don’t bother because there’s no beach. The day-trippers cluster in Positano and Amalfi. Ravello is quiet.

Villa Cimbrone’s Terrace of Infinity is one of the most extraordinary views I’ve found anywhere in Italy — a stone terrace at the edge of a cliff, lined with marble busts, looking straight out over the Tyrrhenian Sea. Gore Vidal lived in Ravello for decades. Wagner wrote part of Parsifal here. The town itself is small enough to walk completely in an hour, and the two villa gardens (Cimbrone and Rufolo) are each worth the SITA bus ride up from Amalfi.

Three hours in Ravello beats a full day fighting the crowds in Positano. I’d go back before I’d go back to most of the coast.

7. Venice needs exactly two days

Day one: arrive, put the map away, get lost. The getting-lost part is not optional and not a cliche — Venice is the only city I know where navigating by landmark and instinct is genuinely more efficient than GPS, which routes you onto bridges that are under repair and through alleys that dead-end at canals. Eat cicchetti at a bàcaro, which are the Venetian equivalent of tapas bars and usually cost €1.50 to €2 per piece. Take the vaporetto Line 1 the length of the Grand Canal. Go to Murano in the afternoon.

Day two: Doge’s Palace first thing, before the cruise ship crowds arrive. San Marco Basilica at 8am when it opens, before the lines form. Rialto market in the morning — it’s a working fish and produce market, not a souvenir stall. Done.

More than two days and you start feeling the seams of the place — the tourism machine, the day-tripper density, the fact that most of the restaurants near San Marco are targeting people who will never return and price accordingly. Two days lets you love it. Three days starts to complicate that.

8. The Vatican Museums are optional

This will be unpopular. The Sistine Chapel is extraordinary. If seeing the Sistine Chapel is on your list, go — book the first entry slot available and accept that you will be in a crowd. The ceiling is worth it.

But if you’re going because it feels obligatory, consider that Rome’s churches contain comparable concentrations of Renaissance and Baroque art with almost no crowds and free entry. San Clemente has a fourth-century basilica built over a second-century Mithraeum built over a first-century Roman house — three layers of history, €10 to descend, and usually twenty other people inside. Santa Maria Maggiore has fifth-century mosaics that survive from before the fall of the Western Roman Empire. The Pantheon is 2,000 years old and geometrically perfect and you can stand in the center of it without being ushered along by a rope line.

Rome is not short on extraordinary things. The Vatican Museums require three hours minimum, significant advance booking, and the kind of crowd density that makes it hard to actually see the art. Know what you’re trading.

9. Shoulder season changes everything

Late September or May. Those are the windows. The difference between August in Rome and September in Rome is the difference between a fever dream and a functional city. August is 38 degrees, sold-out restaurants, €50 extra per night on every hotel, and crowds that make the Colosseum feel like a subway car at rush hour.

Late September is warm enough for the coast, cool enough for Rome and Florence to be comfortable on foot, and the crowds at major sites thin noticeably after the first week. I’ve paid €90 per night in late September at a hotel that was €160 in August and €190 in July. The Amalfi Coast specifically becomes manageable — the SITA buses aren’t standing room only, the ferries have seats, Positano is still beautiful but the restaurant wait times drop from 90 minutes to 20.

May has the same logic but risks more rain on the coast. Both work. August is survivable but you are paying a premium in every possible way to have a harder experience.

10. Italian train tickets must be validated

This one catches people every single trip. Regional train tickets in Italy are not valid when you buy them — they are valid for a specific window after you stamp them in the yellow validation machine at the platform entrance. The machine prints the date and time on the ticket. That’s when your ticket becomes active.

Inspectors check, and the fine for an unvalidated ticket is €50 regardless of whether you bought the ticket and simply forgot to stamp it. “I didn’t know” does not move them. I’ve watched it happen to other travelers more than once.

This applies to regional trains — Circumvesuviana, regional Trenitalia services, intercity buses that use paper tickets. It does not apply to high-speed trains (Frecciarossa, Italo) which have assigned seats tied to your booking. If you’re not sure which type of train you’re on, validate anyway. The machine is at the platform entrance, usually bright yellow, and takes two seconds.

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Planning your Italy trip?

More detail on specific destinations and logistics is in these posts:

• Rome: what to see, where to eat, and how to avoid the worst of the crowds
• The Amalfi Coast: a practical guide to getting there and getting around
• Italian trains explained: high-speed vs. regional, booking platforms, and validation
• What I’d Do Differently: the full series index

Travel Tools We Actually Use

Rome means 15,000-20,000 steps a day on cobblestones. The Amalfi Coast means ferry schedules that change with the weather. Italy rewards preparation.

• eSIM Data: Airalo eSIM for Italy — You need data for Trenitalia schedules, ferry updates on the Amalfi Coast, and Google Maps in cities where streets have no signs.
• Car Rental: Compare car rental prices for Italy — Essential for Tuscany and the South of France leg. Do NOT rent for the Amalfi Coast — the road is single-lane with buses and parking is nonexistent. Use SITA buses and ferries instead.
• Travel Insurance: — Amalfi Coast ferry cancellations in bad weather can strand you. Insurance that covers trip disruption is worth it.
• Money: — Best euro exchange rate. Many small trattorias are cash-preferred.
• Train App: Download Trenitalia or the Trainline app — book in advance for the best prices, and remember that regional train tickets must be validated before boarding.

Book Tours and Activities

• Skip-the-Line Colosseum Tour
• Amalfi Coast Boat Tour from Naples
• Pompeii Guided Tour

Gear That Saved Us in Europe

• Osprey Farpoint 40 Travel Backpack – Fits in overhead bins on budget European airlines.
• Anker Nano Power Bank – Long museum and walking days drain your phone.
• Airalo eSIM – One eSIM for all of Europe.
• Universal Travel Adapter – EU, UK, and Swiss plugs are all different.
• Packing Cubes – Keeps your bag organized across multiple cities.
• Rain Jacket (Marmot Precip) – Weather changes fast in shoulder season.

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Plan Your Trip to Italy

Ready to book? Search flights to Italy to compare prices across airlines. And compare hotel rates in Italy to find the best deals for your dates.

Affiliate disclosure: This post contains affiliate links. I earn a small commission if you book through them, at no extra cost to you. Links: SafetyWing travel insurance (10% off), Skyscanner for flights, Airalo eSIM for data, GetYourGuide for tours, Booking.com for hotels, Viator for tours.