Finding Italy

Getting There, Parte Uno

Driving and renting in Italy

I started writing this post with the intent of helping others not make the same mistakes as I’ve made.  By the time I’d finished writing about my first experience driving and renting in 2010, I realized I’d made so many mistakes driving that I would have to do at least one more post on driving and renting plus a post on trains.

Neither renting nor driving in a foreign country is easy, especially Italy and France, where the local drivers show no mercy.  I remember the trip leader on my first bike trip in Italy saying that local drivers consider traffic laws and lights just a suggestion and I’ve found that to be an accurate statement over the years.  Hopefully the mistakes I’ve made will help someone else.

And you may be asking yourself, why bother with renting and driving?  During our 2017 trip we used trains only, going from Florence to Verona, to Padua, to Venice and back to Florence.  Other than the hassle of getting bags up and down platforms we had no issues but we did miss not being able to drive to vineyards or towns in the countryside.

And that’s the main reason for renting and driving.  In areas such as Chianti, southern Tuscany and the Garfagnana north of Lucca, a car is a necessity since there’s no train service between many of the towns and the whole point of being there is to explore the countryside.

My first four trips to Italy and France involved bike trips or volunteer trips (see Flying solo) where all I had to do was meet the group at a designated location.  You wouldn’t guess it to read the mishaps I describe below but I view myself as a good map reader and I thoroughly research the routes as well as contact hotels for directions; yet something always happens.  Plus as I said in my Provence, Provence, wherefore art thou Provence? post, my sister is a great person but map reading is not in her skill set.  More than once after asking my sister to check where we were, I’ve pulled to the side of the road and snatched the map out of her hand to figure it out myself.

My first experience with renting and driving was in 2010.  My sister initially asked me to go with her to Scotland for the world wide McNeil clan reunion, my mother’s clan.  I agreed and then she asked if we could add a week in Italy before or after the reunion.  She had heard me talk incessantly about how much I loved Italy and wanted to see the places I’d been to on my bike trip.  The reunion was the first week in August and knowing that most Europeans take their vacations in August making many places crowded and other places closed, I suggested going to Italy the week before the reunion.

It was already a logistical nightmare and I made it worse by booking each leg piecemeal, trying to find the cheapest fare for each route.  Plus knowing what I know now I would have booked a flight from London to Florence, then driven from Florence to Rome, stopping near Siena and in Montalcino, and flown back from Rome.  But I booked us round trip from Chicago to  London and London  to Rome and left way too much time between flights.  We didn’t get into Rome until nearly 7:00pm.  After getting our bags which took forever, we found that the car rental office was in a parking garage across from the terminal and had to schlep over there, do the paper work and then get on the autostrada headed to our first stop of Montalcino.

It’s a miracle we even got out of Rome and after about an hour on the autostrada, I realized the gauge I thought was for gas was for engine temperature and we were almost out of gas.  Thankfully the autostrade in Italy and autoroutes in France have service areas with gas stations where you can quickly pull off and gas up.  Still it was pitch black when we got off the autostrada at Montepulciano and headed west towards Montalcino.  We were getting close to Montalcino but I was totally confused over the road signs and had to stop at a gas station and fumble my way through asking directions.

I managed to get us to Montalcino but  then the fun began.  I knew from my bike trip that Montalcino, like many Italian towns, is a hill town with a ‘centro’ closed to cars unless you are a local.  I wrote in my journal (and my Montalcino and Southern Tuscany post) ‘Even with maps and good directions from the owner of the B&B where we were staying—Palazzina Cesira—I had to abandon the car  and walk to a gelato shop where I got directions to the B&B.’

The narrow streets outside Palazzina Cesira

Our host Roberto was relieved that we had made it and showed us how to get the car closer to the B&B to unload our bags and then where to park on the edge of town. Hotels and B&B’s in the centro of Montalcino can give their guests parking passes for an area on the outskirts of town.

Montalcino car park

That was just the beginning of the excitement.  On our first day I was trying to follow the route we took to Pienza on my  bike trip.

I lost track of the number of times I went through the roundabout on the southwest edge of Montalcino and ended up on the road to Banfi.  But I finally checked our map and saw what looked like a short cut to the road I wanted to be on (the road to Sant’Antimo and Bagno Vingoni) but it ended in a tiny hill top village and every time I tried to back up our car to turn around, it went forward until we were right against the wall. I got out of the car and asked a local for help and he turned it around it 10 seconds.  In the process I put a nice scrape on the bumper.

This may be a good place to write about my love/hate relationship with roundabouts.  I’ve learned over the years that it’s relatively easy to keep circling a roundabout until you figure which road to take.  I’ve also learned that hesitating in a roundabout can lead to yelling and honking from locals–and that’s on a good day.  Unfortunately there are many roundabouts with so many signs that it’s almost impossible to tell what direction to go.  I thought I had a good picture of a roundabout but couldn’t find it.  the picture below shows a typical Tuscan road and if you look closely, you’ll see some of the crazy Italian signs.

Driving through the Tuscan countryside

I have a book called Wicked Italian which makes up hilarious explanations for the signs.

Our next round of chaos occurred on the leg from Siena to Hotel Belvedere di San Leonino just northwest of Siena.  Roberto gave us excellent directions to get to Buonconvento and then on into Siena.  We detoured from Buonconvento to Abbazia Monte Oliveto (see Cathedrals and Abbeys) before going to Siena, but that’s an easy detour.  Roberto’s directions took us to the parking area SE of the campo and we had no problem finding it.

near Porta Romana

But after wandering the city for several hours and returning to the parking area, we circled  the west side of the centro for what seemed like hours before stumbling on to the SS222 from which we could take the road to Hotel Belvedere. ( see my Where to stay post)

I don’t recall any major issues as I showed my sister the towns of Chianti that I love–  other than her screaming every time a local passed us on a blind curve.  We drove to Radda, Castellina, Gaiole as well as Ceramiche Rampini and Badia Coltibuono without any problems.  After our stay at Hotel Belvedere we took the Chianti Highway (SS222) that winds through beautiful vineyards between Siena and Florence.  We stopped in Greve on a market day and walked around exploring all the food. 

We had a hotel reservation on via  Giucciardini in the Oltrarno section of Florence.  I’m not sure how we made it to Porta Romana probably on via Senese from the autostrada.  But it then became Cirque de Soleil as we drove up and down the streets parallel to via Romana which turns into via Giucciardini.  When we finally spotted the hotel (and hotel signs are frequently quite small) we basically abandoned the car on the street in front of the hotel and lugged our suitcases in.  I thought the desk clerk was going to stroke out when we told him the car was on the street, repeating ‘In front of the hotel?’ in a higher and higher voice.  He finally calmed down and told us where to take the car, a parking area near Porta Romana.

Along via de Guicciardini in front of Hotel Scaletta
Via de Guicciardini

On our last day in Italy  we drove all the way from Firenze to Rome, using the A1 autostrada  Roma.  I dropped my sister and our bags off at the terminal then found my way into the parking structure and the rental office.  We lucked out in that the computers weren’t working and so they didn’t inspect the car or charge us for the boo boo on the bumper.


In 2014 my sister asked if I wanted to go to Italy again.  The first week morphed into a trip with my sister, niece and two of my niece’s friends, starting in Florence, then driving to Chianti and Hotel Belvedere then Montalcino.  After driving my niece and friends back to Florence, we then changed cars, picked up my daughter and drove back to Montalcino.

My first word of advice on renting in Florence.  If at all possible, do not rent at the airport and do not rent from Hertz. The rental car office is very difficult to find when you’re dropping off a car mainly because the roundabout near the airport is one of the worst in terms of being able to get in the right lane for the street to the rental lot.  If you miss the turn, you’ll be on the main street heading for the centro.  More importantly  the airport offices and Hertz in particular charge astronomical fees which can multiply the cost of your rental several times over (more on that in my More European Driving Adventures post.)

I came into Florence a few days before the rest of the gang and on the day they arrived I took the airport shuttle (5 euros) from Santa Maria Novella train station.  After meeting everyone we took the rental car shuttle to the lot and did the paperwork for our car.  I thought it would be easier to take the autostrada from the airport to the exit for the centro rather than driving across the city.  NOPE  First I got us going the wrong way, then we couldn’t figure out how to pay the tolls.  When I finally got us on the street along the Arno, I kept putting the car into 1st gear rather than 3rd and killing the engine.  I finally made it to the hotel amidst a flotilla of honking Italian drivers. We were definitely ready for a drink by then.

Enjoying the terrace at Hotel Silla

The staff at Hotel Silla ( Where to stay ) gave us good directions for heading to Chianti, first driving along the Lungarno and then into the ‘burbs’ surrounding Firenze.  That led us to the road through Impruneta and onto the Chianti Highway (SS222).  Here is the map of Chianti and the 222 that I’ve used for exploring this area.  It is an absolutely gorgeous drive through Greve and Castellina to the tiny village of San Leonino 

The only problem we had our first full day in Chianti was that everyone was hungover and we had to take a long break at Badia a Coltibuono walking from the shop to the abbey to let the fresh pine laden air do its magic.

Badia a Coltibuono

Our second day at Belvedere, the hotel had arranged for a tour of Siena and as I wrote in my Siena to St. Gimignano post it was challenging getting in and out of Siena and finding parking as you can see in these pictures near Porta Camollia and San Domenica.

Still it was worth the roundabout nightmare for the tour which is one of the best I’ve ever taken.

The staff at Belvedere who are generally very helpful gave us less than great directions to Montalcino and once again I had to stop at a gas station south of Siena and then was able to get us to Buonconvento where we stopped for real Italian coffee.

A real bar in Buonconvento

In another deja vu moment I missed the turn to the B&B in Montalcino and had to park on the outskirts, walk to Palazzina, get directions, drop off our bags then take my niece and her friends to the hotel where I stayed on my second bike trip.  (I recently read my 2014 Journal and realized I was pretty upset most of the time because I thought everyone was criticizing my driving and I was super relieved to get my niece and her friends back to Florence.)

After a day and a half in Montalcino we drove back to Florence and dropped off my niece and her friends at their hotel. Then we headed back out to the airport to drop off one car and pick up my daughter and rent another car.  It was a Sunday and when we stopped at a gas station to fill up before returning the car, we realized that the stations were closed and we had no idea how to use the pay at the pump option.  My sister was near hysteria when a little guy rode up on his bike and showed us how to pay, then he offered to guide us to the car rental office.  He asked for 5 euros but it was worth every penny.  We never would have found it otherwise.

Roberto, our host at Palazzina Cesira in Montalcino, had given us excellent directions from Montalcino to the Firenze-Siena highway and we had no problem getting back to Montalcino after picking up my daughter.  This time I got us going the right direction on the autostrada and it’s just a few kilometers to the Fi-Si exit. (As an aside, all autostrade are toll roads and in some cases you can pay with a credit card and other times you need cash.  I try to avoid the toll roads but if there’s no other choice, I make sure I have cash.  As discussed below, those costs can be significant.)

After another day and a half in Montalcino with side trips to Pienza, Sant’Antimo and Banfi,


we drove to San Gimignano.  We used Roberto’s good directions to the Fi-Si highway, then exited at Poggibonsi Nord and followed the signs to San Gimignano.  I had booked us into Hotel Antico Posso

Courtyard of Hotel Antico Posso

in the centro and was super nervous about getting us there.  I had printed off the map and directions from their web site but what really helped me was a video on their web site.

As we were nearing San Gimignano, I asked my daughter to check the directions I’d printed off and she looked at me like I had two heads.  But I quickly started seeing the signs and streets that I’d seen in the video.  I later wrote in my journal, ‘Despite L giving me grief for it, I am so glad I watched that video 52 times ‘cause I got us right here, no problem.’  After unloading the car, I had to drive it back to the parking area outside the walls.  Unlike Montalcino, the hotels don’t give out parking permits and it cost us 30 euros for 2 1/2 days.

The narrow streets of San Gimignano

From San Gimignano we drove back to Hotel Belvedere with just a minor glitch in Poggibonsi  Nord where I had to stop to get directions for the road to Castellina.  After a day and a half at Belvedere we had to drive to Ladispoli, a small town on the coast just north of Rome so my daughter could catch her flight the next morning.  From the Fi-Si highway we picked up S235 which took us around Grossetto and to the A12/E80 past Civitavecchia into Ladispoli.  My sister reminded me recently how we circled the city for an hour looking for our hotel (rivaling my recent experience in Perugia.)

We finally found Hotel Alle Tamirici.  The location was lovely; the hotel not so much.

Hotel Alle Tamerici

We spent a couple of hours walking along the beach then having a beer watching the sun set.

But after dinner in the hotel’s restaurant we were kept awake most of the night by a loud party that eventually led me to stomp into the dining room in my PJ’s demanding that they quiet down.  Plus when we got up we realized the time had changed from DST and we weren’t sure we would make it to the airport in time.  But other than a couple of loops around the airport before finding the right terminal we had no problems.

I returned to Ladispoli to pick up my sister, finding her totally freaked that we wouldn’t get the car back to Florence in time.  But again, we had no problems.

That leads me to my WORST decision of the trip.  I thought it would be easier and more cost effective to rent a car one way from Florence to Milan.  Boy was I wrong!  DO NOT DO THIS.

As part of my plan I booked us in to Hotel Villa Betania– Where to stay -which is in a lovely area about a mile from the centro.  In retrospect I’m not sure why I chose it but it was a fortuitous choice and we’ve returned in 2015 and 2018.  So when we got back to Florence that Sunday, we first dropped off our luggage at the hotel then returned our car, took the shuttle back to the centro and spent the afternoon at the Accademia (Museums, monuments and interesting sights), then walked to Villa Betania and enjoyed their garden.

The garden at Villa Betania

I think we left the next morning, cabbing it to the car rental office at the airport and picking up our car.  Then the fun began.  The autostrada between Florence and Bologna is two lanes each way, going through one mountain tunnel after another, with nose to nose trucks in the slow lane.  So you have the choice of getting stuck behind miles of trucks or driving 900 mph in the fast lane.  On the rare occasion I tried going around the trucks at less than warp speed, the Italian drivers let me know in no uncertain terms that this was not the correct way to drive.

When we got off the autostrada near Milan, I think we had to pay at least 40 euros in tolls.  I thought we were home free but we still had miles to go before finding the road to the airport and our hotel.  While our hotel had sent me detailed instructions on which roads to take, I clearly remember a trucker honking and giving me the Italian salute when I tried to exit.

By then it was dark, and it took me a couple of loops to find the hotel.  We quickly checked in, then drove to the airport which we circled a couple of times before finding the rental car drop off point.  The woman checking us in suggested we go get gas at a station near the airport but we were done and took the penalty.  After being picked up by the hotel shuttle, we spent the evening drinking in the bar.

So my next ‘driving and renting’ post will include 2015, 2016 and 2018.  I made an especially big mistake in 2015 and will include information on it, as well as the fun time trying to find the car rental office in Perugia.





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