- Originally published July 2024, updated April 2025
We have fallen head over heels in love! Of course, saying we have fallen in love with Tuscany is not a shocking statement. It seems almost impossible to travel anywhere in Tuscany and not love every moment. But we loved it even more than we expected. There is so much to see and do in Tuscany, but our travels focused mainly on Montepulciano. After visiting a few times since 2022, we figured out a few things along the way we want to share. We are by no means experts, just some real life learnings to help you on your journey through magical Tuscany.
There’s plenty to cover, so we’ll discuss more in upcoming posts. But for now, let’s start with getting there and getting around. You will have a few decisions to make!
Flying to the area
Unless you are visiting from a near by country, where traveling by train is an option, you’re flying in. Montepulciano is about an hour
and a half from Florence’s Amerigo Vespucci airport (FLR) and about two and a half hours from Rome’s Leonardo da Vinci Fiumicino airport (FCO). Although Florence is closer, it will almost certainly guarantee you at least one connection (possibly 2). So if you’re not planning on spending time in Florence, Rome will definitely give you more flight options. Even if you spend time in Florence, Rome may still be the way to go. For us, since we had to make at least one connection already, Rome was the best choice. Since we had plenty of time between landing and check in, it was the perfect reason to stop in Orvieto on the way. This broke up the drive to Montepulciano, we could stop for lunch, and it was a great opportunity to see another wonderful town. We’ll talk about Orvieto more a little later. However, if you’re looking for some great travel shows that give you a glimpse into this beautiful town, make sure to check out Stanley Tucci’s show – Searching for Italy (episode on Umbria) and Chef Nisha Katona’s show – A Taste of Italy and her episode dedicated entirely to Orvieto.
Now you’ve made it to Italy, you have an even more important decision than your flights. How are you getting around once you you’re there? Are you renting a car? Train and taxis? Getting a driver? There are pros and cons to all options and in the end, it is personal decision based on your comfort level. We have rented a car and we have hired drivers. For us, a driver wins, but for you it might be different. Let’s talk through the pros and cons of each –
Renting a car
Why you would rent a car
- You are in control of when and where you go – this is the main reason to do it and might outweigh any cons for doing it.
- Nothing is really within walking distance, even if it’s close. Even if you stay in town, there is plenty you will want to do and see that is outside of the main area of Montepulciano.
- Although it might not be “cheap”, it will most likely be less than a driver.
Why you might not want to deal with it
- They aren’t called “Tuscan Hill Towns” for nothing! If you live in a mountainous area, this might not be a big deal for you. However, we come from Chicago and now live in Florida, so “mountains” really aren’t our thing. Roads are narrow and winding, there will be curves you can’t see around (yes, we had to honk before going around). The edges can have steep drop offs and “guardrails” aren’t a huge thing on smaller roads. Some roads will also be so narrow that even though they are two way, the reality is one car will need to pull to the side to allow the other to pass. You and/or all those driving need to be good with this.
Other things to consider when driving
- Montepulciano (along with almost every town) have areas called “ZTLs” – Zona Traffico Limitato. For Montepulciano, this is everything inside the walls and where most of the restaurants and shopping are. Signs will warn you, but depending on the town, by the time you see it, you may have no other option. Or depending on the town, the sign might not stand out (we’re looking at you Orvieto). You will see cars going through, you will think it’s ok, it’s not. These are controlled by cameras and you won’t know you’ve gone through one until your rental car company let’s you know you have a ticket coming. Yes, we know from experience.
- Parking is limited around Montepulciano, as well as most towns. Just know that might take you a little bit to find some (looking around is when you might accidentally go through that ZTL). Most likely there is also a parking fee, so look for the boxes to pay for your ticket to display on your dash. Just to be sure before you set off for the day.
- If you plan on visiting wineries, that is the day you might want to hire a driver even if you rented a car. Wine tastings in Italy tend to be generous and if you have lunch with it, you will most certainly have quite a bit of wine. You might want visit multiple wineries in one day. So let someone else do the driving for you so you can just enjoy the day and take in the beautiful Tuscan countryside. See above for “mountainous terrain”.
- Technically if you are driving in Italy (or Europe for that matter), you need an International Driving Permit. We got one for $20 through AAA. You might not need it, you will probably have friends tell you they didn’t get one, were never asked, they didn’t need it to rent a car. And you might also get pulled over and get asked for one. Yes the chances are slim, so for this…you do you. We didn’t want $20 to stand in between us and having issues with the Italian Poliza.
- Our recommendation for renting a car – Hertz at the Rome Airport. It was easy to get to, they are in the parking garage at the airport. Everyone was helpful and our car was in great condition. Also, very easy returns at the end of your trip. *Driving a manual transmission isn’t your thing? Make sure you request an automatic when renting in Italy. Unlike the US, all cars are not automatic. You can certainly get one, but it’s not the norm.
Hiring a driver & using a taxi
Why you would want to hire a driver
- You and/or those with you don’t drive at all or even if you do, you are more comfortable with having someone else navigate the curvy, steep roads of Tuscany.
- You’re traveling with a larger group, so you will need a bigger vehicle (van/SUV) and you don’t want to deal with trying to find parking for it when parking is already limited.
- You’re planning day trips (Siena anyone?) and don’t want to deal with navigating to another area.
Why a driver might not be your thing
- It can add up and you want your budget to go to other things.
- You like the adventure of navigating a new place and you feel like that’s how you get to really see an area. You might also want the flexibility to change plans last minute. Want to sleep in and skip the drive to Siena – no problem.
Other things to consider
- If you don’t rent a car, you can still do a combo of hired driver (advanced plans) and a local taxi you can call as needed. Montepulciano has plenty of local taxi drivers who can take you into town and come get you with a quick call or text when you’re ready to head back to your hotel. A taxi will most likely be far less, so it can be a way to save a little bit on your transportation budget.
- If you hire a driver to take you to another town, most likely you are hiring them for the day. So if you go to Siena, you may have your driver say from 9am (pick up time) to 5pm (when you arrive back at your hotel). This will of course impact the cost. However, once you’ve hired them for the day, you can usually make multiple stops – want to see Cortona but also want to stop to see Castiglione del Lago on your way back? You can plan that. Want to stop at 3 different wineries in one day? No problem.
- In most cases your driver is also a great source of information about the area. They can help recommend restaurants or stores to check out. So you’re getting more than just from point A to point B.
- Our recommendation for hiring a driver – Tuscany Luxury Transfers. The owner, Antonio, is fabulous! He will make sure you have everything you need for your vacation. Although he is located in Tuscany, he can schedule pick up at the Rome airport if needed. He is also fabulous for day trips to other hilltop towns. He does have quite a few drivers and different size vehicles, but he books up quickly! So if you know when you want to go, contact him right away to check for availability.
No matter which way you decide to go, ask a few questions before you make plans. Ask your hotel or B&B if they have recommendations. In our case, we found out it would be best to rent a car at the Rome airport, as there weren’t car rental locations in town. Also, that Hertz might have some of the best options for cars and ease of rental. When it was time to hire a driver, they had recommendations for that as well. Drivers they had used before and trusted. Also make sure you understand the parking situation where you are staying. If it’s a B&B, they will most likely have parking. However, if you’re staying at a hotel in the heart of town, parking might be limited.
- Update from our recent stay at Borgo San Vincenzo. There are at least some rental options close to Montepulciano. They offered us assistance with a rental car once we got to the hotel, if we didn’t want to rent one in Rome. This is something you might want to look in to if you want to rent a car, but maybe not every day of your stay.
This might not be the glamorous or fun part of planning a trip to Italy, but it’s an important detail of your trip and one that will impact everything. We think it’s definitely worth the time to think about before hand so when you’re there you’re just focused on la dolce vita. 😊 What has been your experience traveling through Italy? What is your preferred mode of transportation when visiting?
