This is how we did it...
Planning
- reserving the rental car. The actual reserving of the car was pretty easy. I just went online and compared a few deals on kayak. I chose Budget but most of the rentals seemed pretty comparable. I knew I didn't want the smallest car since I heard you would basically get a smart car that could barely hold any luggage. I also knew I wanted a gps system in english and automatic transmission (which unfortunately costs more). I basically made my reservation and got a confirmation and that was it! (Tip - I did make sure that the rental office was near our hotel in Florence so ideally we could just walk there to pick up the car.)
- international driving permit. Although most people I know didn't bother getting the permit, it is actually a legal requirement. I think most people either don't know about the requirement or they hope they won't get stopped in Italy by a police officer. But if you do get pulled over for speeding or even at a routine checkpoint, they may ask to see your permit and if you don't have one, I've read that it can be quite a hassle. I believe the purpose of the permit is simply to confirm that you have a driver's license in your home country that is in good standing. Since it was only $15 and I'm an attorney and by nature risk-adverse, I insisted that we get one. The process was super easy - I downloaded the application from the AAA website, got 2 passport photos (sign the back of each) and paid $15 at a AAA location and voila! we got our international driving permit in about 10 minutes. (And no, we never got stopped and no one asked to see it, but $15 for peace of mind is worth it in my book.)
- photo tickets. This is more of a warning, but don't speed in Italy - even if you think no one is watching! A friend of mine went to Italy last year and drove through Tuscany. Six months after she got back, she got a photo ticket in the mail for speeding. Obviously she paid it (it was around $300) since she would have had to return to Italy to appeal it. We all know that it is highly unlikely that anyone would fly back to Italy just to appeal a photo traffic ticket, so the lesson here is simply - DON'T SPEED. No one wants a ticket to be a souvenir for a trip.
Our speedy little car!
- choose a convenient location for pick-up/drop-off. Because I intentionally picked a hotel that was within walking distance of the rental location, it was very easy for us to walk over there to pick up the car. We actually left our luggage at the hotel, picked up the car, and then drove back to the hotel to get our luggage. This was easier for us then dragging all of our luggage to the rental location which is what I saw everyone else in the waiting area doing.
- be patient and carefully check your car. Despite my reservation clearly stating I wanted automatic transmission and confirming it with the customer service agent at pick-up, the car they brought out was still a manual transmission vehicle. We sorted it out and they brought out the correct vehicle. Then we did a careful walk-through to check for existing damage. You don't want to get penalized for existing damages.
- go early if you can to get a gps. They only have a set number of gps units and they go fast. I wasn't able to "reserve" one over the internet or phone, so it would just be safer to get there early and grab one. Alternatively, if your smart phone works in Italy and you are able to use map apps, then you should be ok. I found the standard map app on my iphone was better than the google map app all over Italy, except for Siena and Capri.
- give yourself ample time. The whole pick-up process (due to several errors by the agent) was over an hour. Don't assume you'll be able to get your car quickly and leave and rush to your next destination. Give yourself a cushion period so you won't stress out or be late. Actually, don't assume anything happens quickly in Italy.
Driving from Florence to Greve in Chianti
Once we got our speedy little BMW hatchback we felt relieved and happy. Our gps (and the very clear signage) led us out of the tiny streets of Florence and onto the main road to Greve in Chianti. The drive was relatively smooth and easy. Before we knew it, we were surrounded by lush green hillsides and trees. It truly is like being in a movie because it is exactly like what you see in films set in Tuscany. In about 30 minutes we arrived at our hotel. (yay!) Tip - The hotel parking was included in our room rate, but lots of hotels in Italy charge you an extra parking fee. When booking your hotel, make sure to check if parking is included and/or how much the fee will be. In some hotels it was as much as 30 euros a day!
We stayed at Castello Vicchiomaggio, which was about a 7 minute drive from the town square. The town had free parking lots so it was very easy to stop into town for meals and shopping.
Driving from Greve in Chianti to Siena
The ride was very scenic, lush .... but a tad scary. The winding road was made more hectic by the hoards of cyclists who insisted on sharing the narrow path with the cars. I couldn't tell if this was just a normal Sunday tradition or if these cyclists were doing this in solidarity with the Tour de France that was happening at the same time in France. Regardless, it did make the drive more stressful and slower.
It took us about 50 minutes to get to Siena, but then it took us another 25 minutes to find a parking lot. I had read it was difficult to find parking in Siena and that it could be quite expensive. We did have an address for a lot, but our gps system and my phone were directing us in circles. Being on a hill utterly confused both systems. Fortunately my husband found a lot and even though we weren't certain how much it would cost, we were just happy to park. (It turned out to be about 8 euros for the afternoon, so it wasn't terrible.) Tip: Get clear directions from your hotel on where to park in Siena if you plan on driving to Siena.
The drive back was much more restful. But we did leave on the earlier side since we did not want to risk driving back in the dark.
Overall this drive was ok, but if you are nervous there are alternatives. I believe you can take a bus to Siena or join a tour.
Driving from Greve in Chianti to Florence (the Mall - outlet shopping)
The drive from Greve in Chianti to the Mall (shopping outlet) outside of Florence was definitely more stressful than our other drives. There were multiple turn-abouts and toll-booths. Eeeek! Ultimately we made it to our destination (probably an hour's drive from Greve in Chianti) but I was grateful my husband was willing to take me since I would have been too scared to attempt the drive myself.
Tip: From Florence you can take a bus, a tour or hire a driver/taxi to take you to the Mall.
Returning the car
We returned to Florence and found some free parking near the outskirts of town at a local park because we wanted to eat at Trattoria La Casalinga again. Then from there we returned the car. They inspected it quickly and we got our receipt and were on our way in about 10-15 minutes. We picked the option where we didn't have to fill the gas tank which made the return easier, but there were lots of gas stations outside of the city so if you wanted to fuel up before returning the car, it shouldn't be difficult. (Note- the prices are for each liter, not per gallon.)
In total we had the car for 4 days - including insurance, gps, fuel option - and it cost us about $1000 USD. Expensive, yes, but it was a fun experience.
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