Milan to Tuscany

Hi, Giangilberto from Milan, first of all, since Florence is in Tuscany, I recommend spending all three nights at an agriturismo (farmhouse), for instance, in the Chianti area, which is less than an hour away from Florence.
Since you’ve decided to rent a car, you can easily travel back and forth to visit Florence for the day, in my opinion, there is no need to stay in the city itself.
Here are some tips to help you avoid fines related to Florence’s ZTL (Limited Traffic Zone). It is divided into five sectors, and fines can arrive months later via your car rental agency.
There are two options regarding the daily permit, which you can purchase yourself: 5 euros for transit only, or 15 euros if you also want to park, you must print it out and display it on your dashboard.
However, an even better solution is the "T2 Guidoni" park-and-ride facility, you leave your car outside the city center and take the tram in for 1.50 euros. If you are staying at an agriturismo outside the city, this is the option I would choose, you don't enter the ZTL, you don't have to buy permits, and you avoid any risk.

I have a question: what time of year are you planning your trip?

I ask because from April through the first Sunday of October, there is a night-time ZTL in effect on Thursdays, Fridays, and Saturdays from 11:00 PM to 3:00 AM. This covers all five sectors, two of them, F and G, exist only at night and are not restricted during the day at all.
So, if you plan to go out for dinner, you need to keep this in mind as well.
Finally, I can recommend a lovely agriturismo where my wife and I stayed the last time we visited the area, Fonte de' Medici Country House & Restaurant.
It is located about 45 minutes from Florence, we had a wonderful time there, and the setting is enchanting.

https://fontedemedici.it/en.html

Giangilberto, I'm learning a lot from your additions on the Forum, just copied the agriturismo recommendation to my Florence notes, so thank you!

Thank you very much Sandancisco, it’s a pleasure to have someone like you, who has been contributing to the forum for years, thank me publicly. It encourages me to keep making my own contributions.

Where is the conference? In Milan? If you are flying to Milan and then have to be there 3 days later, you might want to consider someplace closer, if you haven’t been before.

Lake Maggiore is near the Malpensa airport. Lake Como is also near Milan, just to mention two popular destinations. There will be agriturismi in northern Italy too.

Driving from the Milan area to Tuscany is a chore to me. Long and boring drive on the A1 freeway. Im not even sure if I’d rent a car. You can’t use it in Florence, you can’t use it in Milan. If you are determined to go to Tuscany at an agriturismo, I would use the high speed train, then maybe rent in Florence or Arezzo or Chiusi, go to the agriturismo, then return the car in Florence, and take the train back to Milan for the conference.

Hello joan.dekoven, and welcome to the forum,

You don't say whether you will be staying in Milan the first night or plan on rolling off the plane and heading to Tuscany, which is what it sounds like you're planning on. I'm not sure I would get off an international flight and then think renting a car and driving from Milan to Florence was a good idea.

If you're flying internationally you're probably going to come into Malpensa MXP which is outside the city. The train from Milan to Florence will be faster and way less stress than driving the same distance. I think staying the first night in Florence, seeing the city the next day and then renting a car to see some countryside from there makes sense. You could return the car in Florence and then fast train back to Milan in time for your conference. If you are planning on staying in Milan the day you land then do that and book a fast train in advance early then next day to head out.

There are many, many agriturismos out there and I'm sure everyone has their favorite. If I was going to this I would look for one near Buonconvento which is a tiny town south of Siena. It offers easy driving access to Pienza and the other famous southern Tuscan towns as well as train and bus service to Siena so you can visit for dinner with wine and not worry about driving back.

As others have said there is beautiful lakes areas much closer to Milan if you wand to maximize your vacation time but if rural Tuscany calls to you then I think something like this is a workable plan. It is as beautiful as advertised.

Usual rental car notes:
- All drivers need an IDP before leaving the states
- Read up on ZTLs before you leave the states and locally before you visit any popular town (also speed cameras are common now)
- Add at least 25% to Google drive times for rural driving, GPS is a must, be mentally prepared for getting lost

Have a great trip,
=Tod

Don't assume that because you buy the 15 euro access and parking permit, you will easily find parking in the Florence centre; it will likely be a difficult hunt. BTW, I have observed that the Florence municipality is marking a lot of places (basically, the only places you could find) as residents only.

There are lots of Americans, maybe not familiar with Europe or Italy, who think they can drive in Italy with the same ease they can do in American cities.
That is not the case. Cities have traffic restrictions that make it impossible to drive in large portions of the cities. Streets are often narrow and congested, so one has to be skilled enough to be able to maneuver a car in very narrow spaces. Parking is difficult to non existent. Even driving on the freeway is more stressful. You can only pass cars on the left, the left lane is for passing only, and if you linger on it longer than necessary, the fast drivers behind you will be inches from your rear bumper pressuring you to move over, sometimes they blast the horn to make sure you do quickly. Also, while in the left passing lane, maybe driving at 80 mph, you will be just inches from the median guardrail. There is not an inch of space between the left stripe of the left lane and the guardrail. If you get distracted one second you might scrape it. Distracted driving is not an option in Italy. You must stay focused. And modern cars will remind you. Last month I rented a brand new MG HS Hybrid SUV. Every time I yawned, a message with the image of a coffee cup came up on the display suggesting I take a coffee break. Every time I got distracted and got too close to the left side or to the median, another message came up on the display saying: "please don't get distracted and focus on driving!".

https://reason.com/2026/09/13/your-car-is-watching-you/

Thank you everyone. Our conference is in Como so we will end up there. Looks like taking a train is a better option than renting a car.
Any other suggestions on an aguraturisimo? The one mentioned above is not available.
We are going on Oct 12, 2026. Kind of a last minute trip.

If you’ve never been, you can try Cernobbio. It’s on the lake and very close to Como. It’s one of the most famous towns. Menaggio is another option to consider. Just across the lake from Varenna and Bellagio, all easily reachable by ferry. From Memaggio you can also take a day trip to Lugano (there is a bus).
Menaggio, Bellagio, are all reachable from Como by ferry or bus. You could also rent a car in Como. There are rental agencies in town, however you don’t really need one.
An agriturismo is a farmhouse that is being converted to a vacation villa. They are newly always in the middle of the countryside and that type of stay almost certainly requires a car, since they are not well served by public transportation.
I have never stayed at an agriturismo in northern Italy but you can find plenty in several websites. Just Google “siti web agriturismi” and a bunch of agriturismi search websites will come up.

How many nights do you actually have?
Sounds like just 3 and that is really only 2 days

Arrive Milan -travel to Tuscany- this will take at least half a day-jet lagged as well
Spend next day and night in Tuscany
Third day/night-will you need to start heading back up to Como?
What time do you need to be there for the conference?

As mentioned above you need a car for Tuscany
Driving from MXP to Tuscany after what I assume is an overnight flight is not a good idea

Why not just spend your very short bit of time at Lake Como or Lake Maggiore rather than spending so much time to travel to/from further away?

If you want to see Florence then just train there and stay til you need to leave for Como. You might be able to book a guided bus tour to a few Tuscan hilltowns

Availability in Tuscany and the lakes will be very limited-those places book up early