Tuscan Driver for 5 days?

If you are renting a car, I assume you know how to drive, so personally I wouldn't throw money away on a private driver on top to the rental. Driving in Tuscany is not difficult if you can deal with curvy roads and hills. Just make sure you research the topic (International driving permit requirements, European road signs, Limited Traffic Zone restrictions).

I don't know what reasonable means to you, but the cost of a private driver (noleggio con conducente, in Italian) at you disposal is approximately 30€-€40 per hour, plus mileage cost (€0.70-€0.80 per km) although often the first 100km (60 miles) are included in the first 4 hour price. So an 8 hour Tuscany tour would be in the neighborhood of 350€ and up (depending on vehicle) inclusive of mileage.

You can do that. It would be expensive but very convenient. There are a couple of issues. With a rental car he would not be listed as a driver so he would have to use his own vehicle. I would figure out someway to dump the rental and save that expense. You will have to define "reasonable" but I doubt if you could get a driver and car for less than $500 a day. If that is acceptable to you, then ask your lodging for recommendations. For six days you might get a discount.

This doesn't sound like a good deal if the money you save is money you will have to spend on a driver. This "deal" works for people who want to take advantage of the "drive" part of the deal (even though the town is accessible by regional train and bus). Someone wrote about such a deal a few months back - it turns out she really wanted to take the train (and it would have been cheaper to do so) but she was shoehorned into having a rental car that she didn't even want to use. So, even if it's cheap, it's still not a deal to pay for things that have no value to you and you wouldn't pay for, given a choice. That's why package deals seem attractive until you get to the nitty-gritty details.

Driving in Italy is not difficult nor confusing. Use a GPS and a paper map, learn how to read international road signs(Rick has them in his guide books) and decide if you want to upgrade to an automatic transmission. Most cars, including rentals, are manual shift. The Autostradas are like the Interstate highways in the US. A driver for six days is going to negate any savings you made on your "Fly and Drive" package.

No matter what anyone tells you, driving in a foreign country takes courage. If you lack enough courage to give you motivation, then you should probably not drive in Italy. Not every person is meant to get behind the wheel of a car. I have relatives in the Midwest who refuse to drive on a freeway in their hometown because they're afraid. I would never suggest they rent a car in Italy.

There are private drivers available for tours in Tuscany. Some are quite well known. I imagine a 5-day hire would cost a fortune, but money well spent if visiting Tuscany is on your bucket list and you really don't want the responsibility of driving the car.

Sharing your rental vehicle with another driver requires a signed legal contract. That would not be an easy thing to accomplish with someone locally. It's better to simply hire someone who does this sort of thing for a living. Some of the well-known drivers are well informed with their history. They can make excellent tour guides.

I don't want to overstate the obvious from the comments above, but if this is a fabulous "Fly and Drive" deal, you really should want to drive on your own.....

It loses its "deal" appeal if you don't want half of the deal !

is it possible to hire a driver for 6 days for a "reasonable" price

What's your idea of reasonable? It would certainly not be inexpensive for 6 days but what you're willing to pay may be well beyond what's considered "affordable" for many other budgets.

We could us our rental car

As already explained, that's not a viable plan. If a chunk of your package includes a rental car that you do not intend to drive yourself you're essentially throwing money away. That's not a "fantastic" deal at all, and especially not if a hired driver can't touch it without contractual/liability complications.

Not every person is meant to get behind the wheel of a car.

I would agree. It works for some people and causes others stress they don't want or need on their holiday. If you can't afford a driver and are uncomfortable driving yourself, there are options for basing in places where public transport is frequent and reasonable, and day-tripping to any number of places is easy. Florence, for instance, is a great base for Lucca, Pisa, Siena and some other locations in the region. You could also splurge and hire a driver for a single day to cover some ground that might be more time-consuming to manage otherwise.

Hiring someone to drive your rental car has too many factors going against it.

1- the driver would have to meet you at the rental office to sign up as an 'authorised additional driver' ( probably a $15 or more per day extra charge not covered in your "deal")

2- once you leave Milan for the countryside your driver will need a place to stay--- if he lives in Milan to have easy access to meet you there for the pick up, he will be 3 hours from Milan, so for him to 'commute' home doesn't work---- he would most likely expect you to pay for lodging and his additional food expense--- if you get a driver to come from Montecatini to meet you in Milan you will have to pay for him to get there and then at the end of the trip to get back home

Unless you have a Bill Gates financial status I doubt the costs would be considered 'reasonable' by very many people

Either get a friend who is comfortable with driving to go with you, or look for some other 'deal' as what you have found does not seem suitable for you

The professional driver will drive his own licensed NCC vehicle, not yours.

Do not contemplate the possibility that the NCC driver will drive your vehicle. That is not permitted by current Italian NCC regulations. I doubt you will find any licensed driver risking his/her NCC license to do that. The only way to do so would be to find someone (like a friend) who is unlicensed, willing to drive it, but you would still need to put his name as additional driver in your rental contract, and there would be no enforceable contract in this transaction. It would be a friends' agreement. Such contract would not be enforceable. There is a reason why Uber is illegal in Italy.

We are just completing a 10 day trip in Italy where we had a rented car for 5 nights. (Not in Florence) My husband was the driver and I was the navigator. I found the trip exhilarating, enjoyed going to places on our own schedule and enjoying the beautiful scenery. He found it a little stressful being in unfamiliar territory but not hard. We stayed off the autostada as much as possible. The best decision we made was to rent an automatic car, not sure the added stress of the hills in the hill towns with a manual drive car would have been a good thing. My husband isn’t sure he would rush to do it again but I feel a great sense of accomplishment for all the places we got to see.

I am unable to give you any recommendations for driver. However I can tell you this: I have done the exact tour you are thinking about. I know the tour company- and they are good. I just got back from the same trip. If you are fearful of driving - then don't. There is a train station in Montecatini and you can go to other towns via that. Also there are buses. If you are traveling alone - I understand your concern about traveling. However if you are traveling with companion - one of you can be the navigator and the other the driver. It's fun. Get a SIM card for your smart phone or device and you will have GPS. It is so reliable you will not even need maps.
Also - Montecatini is a nice town too.

I've used Luca at Hills and Roads as a driver for 2 days on a Tuscany trip I did. You can get an idea of prices and what you consider "reasonable". We priced a couple other driver services out and they gave us the best price. We paid 360 euro a day for the 4 of us. But that wasn't bad when we split it and it was great having a local with us at some towns we stopped at that looked nice driving around.

Roberto knows his stuff. In reply #1, he estimated daily cost at 350 euro.

Robert, ( reply #12) from his personal experience paid 360 euro per day.

The question is what "reasonable" means to you.

Is the trip still a "fantastic price" when you add on the ground transportation cost?

Without knowing what the OP considers reasonable it is very hard to respond further.
I assume the OP has thought about what they are asking and what such a service might cost in their home state?
You are basically paying for someone to be exclusively your personal driver for a week where they cannot make any other money during that time.
Where would this driver sleep, in their car? or would you pay for their lodging or have them return back to their home each evening and come back the next day to pick you up ; if the later you could only venture so far and probably want a driver based in the mid point between Montecatini and Milan/Como for your request to even be possible. Maybe Parma or Bologna based.

The villages in Tuscany are for the most part all south of Montecatini by a fair distance and Milan is north with Lake Como being even north of that. For Lake Como by the way you really don't want to see Como the town but the smaller more northern towns on the lake like Bellagio and Varenna .

To me it sounds insane to others I am sure it is perfectly reasonable.
No professional is going to drive your rental car.