Straight Answers to Common Italy Questions
When to book flights, where you need a car, how to get to Sicily, and what to look for on Torcello—full recording of last night's Ask Me Anything.
Our monthly Ask Me Anything About Italy has become my favorite to do. People come just to hang out, get ideas, and keep their imaginations warm. And in this more intimate atmosphere, I can let my unvarnished opinions fly without comment section bots giving me a hard time. From last night’s Zoom, I harvested a few questions and answers that might be helpful for your own planning.
Paid subscribers can find the full replay below the paywall.
Also, a reminder that if you’re trying to decide which part of Italy to visit, I’m offering a free session called “The Italy Vibe Check” on Monday, February 16th at 7 pm. It’s Presidents’ Day, so hopefully you’ll have off from work. I’ll send the Zoom link on Monday afternoon, so if you’re subscribed here, free or paid, you’ll get the link.
Start with the Flights
When you see an airfare that works for your budget, book it and stop obsessing over “the perfect time.” Airline prices have more to do with fuel and corporate stock than your ability to outsmart the algorithm. Once your dates are confirmed, your trip is real, and you can manage your reservations with clarity. The caveat is that I’m not a points maven or an optimizer. I don’t like feeling paranoid that I missed out on a better deal by not refreshing the browser when Mercury aligned with Pluto. When I find a price that I can afford, I purchase and move on.
Sicily: Train, Plane, or Boat?
We talked about the classic “how do I get to Sicily?” question:
The train: long, scenic, and a bit of a production. You go all the way down Reggio Calabria, the train car gets rolled onto a ferry, you cross the Strait of Messina, and then keep going in Sicily. Romantic, but it’s your whole day.
The plane: there are lots of daily flights to Palermo or Catania. You’ll spend half the day between the airport and security, and then 25 minutes in the air.
The boat: this is the fun one. Overnight ferry from Naples to Palermo. You board around 9–10 pm, have a proper dinner on board, sleep in a cabin, and wake up in Palermo. Very old‑world, very Gen‑X adventure energy. I like to imagine the next installment of the Before Sunrise series has Jesse and Celine boarding the boat for their 25th anniversary, a conversation turns into a fight in the wine-dark sea, which all gets resolved as they pull into Palermo at 6 am.
Renting the Car (and the Boring but Crucial Paperwork)
In places like Tuscany, Puglia, and Sicily, you really do need a car. A guest asked about using Agropoli as a base for exploring Cilento because it has a train, but it’s really for commuters heading into Salerno or Naples, not for people on vacation. All the major rental car companies are in Italy, and you can reserve a car exactly the same as you would anywhere else in the world.
You do need an International Driving Permit. It’s just a piece of paper, hopefully you never need it, but if you get pulled over and the police want to give you a hard time, they can. (One of these days, I’ll tell you the story of my night with the police in Calabria.) It costs $25, and it’s usually free with an AAA membership.
“We Love the Sea, and We’re History People. Now What?”
If you love the sea and you’re traveling with a history buff (or you are the history buff), there’s no better place than Campania.
Naples, Pompeii, Herculaneum, Oplontis, Baia, Paestum, Ischia, and the Cilento. You get ruins, volcanoes, underwater cities, Greek temples, and excellent food, plus the sea. Campania has an embarrassment of riches that are always overlooked in favor of the Amalfi Coast, which, yes, is beautiful, but also not very interesting compared to everything else you can see or do (and eat) within a 2-hour radius of Naples.
Also, a bunch of new discoveries at Oplontis were just announced in late 2025. Archaeologists do most of their digging in the summer when there are students available, so if you can only travel during the scorching months, the upside is that you may see archaeologists at work.
Puglia: The Real Choice You’re Making
In Puglia, don’t agonize over which pretty town is 3% prettier. You’re choosing: interior or sea.
Around Martina Franca and Locorotondo, everything is broadly similar in a good way—whitewashed streets, soft hills, nice food. It’s very easy driving; Puglia is mostly flat, and even the hills aren’t serious hills. The coastline is made of rocks, so I think it’s fine to stay inland and then spend a day at a beach club that makes it possible to enjoy the water without destroying your feet.
If you want the coast, I generally send people to Monopoli instead of Polignano. Polignano is the famous Instagram beach with crowds and “Volare” on repeat all the live long day.
Torcello: Why It’s Worth the Boat Ride
Torcello, an island in the Venetian lagoon, is worth it, but not as a full‑day production. Think of the afternoon into the evening.
You go for the fabulous, unhinged Last Judgment mosaic. You could spend hours staring at this. In particular, on the bottom, there’s a black‑and‑white section of skulls with snakes coming out of their eye sockets. Am I weirdo for loving this so much? Maybe so.
The rhythm is: lunch in Venice, boat out to Torcello, see the mosaics, walk around a bit, maybe a drink, and then head back as the sky turns unicorn pink.
Paid subscribers, the full replay is below.
