We will be visiting Italy for the first time in May and would like to spend 3 nights in the heart of Tuscany. We will be staying in Florence for 4 nights prior and are contemplating renting a car to drive throughout the many hill towns. Of particular interest are Val d'Orcia, Montalcino, Montepulciano, Pienza, Siena, and Chianti.
I have read Stu Dudley's driving guide for Val d' Orcia which sounds wonderful but am wondering if it would be wise to hire a driver/guide for exploring this area. We may also be interested in stopping by a vineyard or 2 for wine tasting so having a driver/guide would be a safe bet. Has anyone hired a private driver/guide for Stu Dudley's Tuscan road trip or would it be possible to hire a driver to follow as directed. Of other interests for the road trip may include olive oil and cheese tasting, shopping (limited), etc. We are considering the Rosewood Castiglion del Bosco for accommdations but are open to suggestions. The Rosewood has a lovely pool which my daughter would enjoy for some downtime. They also advertise Bocce ball which I am interested in learning. We don't need a large villa as it will be myself, my husband, and daughter (age 20). We would also like to visit Orvieto after our time in Tuscany on our way to Rome. Any guidance on how best to schedule this on our itinerary? Should we drive from Tuscany to Orvieto then proceed to Rome where we would drop the car or drop the car in Orvieto and train from there to Rome? Thanks for any advice and suggestions.

I used Luca at hillsandroads.com and it was great. This was not recent, but others here have had a good experience with him. You can tell him what you're interested in and he can suggest an itinerary, or you can tell him the specific places you want to go and he can tell you if it's feasible. I used him for several days, and on the last day, we ended in Orvieto, had time there, and then I took the train to Rome.

I should also add that it would be wonderful to find a church or monastery where we could hear Gregorian chants or sacred songs in Latin. We will be in Cinque Terre on Sunday so will not be in Tuscany on Sunday for mass or services.

You pose several questions....

I wouldn't hire a driver. Doing that for 3 days would cost a fortune, although a good guide could introduce you to towns outside of the typical tourist list.

Visiting wineries can't (usually) be spontaneous as most require reservations, and visiting wineries can also eat up a lot of time which you don't really have. There are enotecas in several towns where you can sample local wines.

If your time frame is 3 nights (2 full days), you'll have to make choices. The Rosewood property is in a good location for exploring the Val d'Orcia. But not Chianti. After you pick up the car in Florence, you could drive through the heart of Chianti (basically, SR222) and see a couple of towns. Overall, the drive to Montalcino on secondary roads (as opposed to the autostrada) would take 3+ hours not counting stops and lunch.

The drive to Siena from the Rosewood would take about an hour, and the drive to Montepulciano would take more than an hour.

You can certainly stop in Orvieto on the way to Rome. If you take the more interesting/scenic roads, the drive will take about 2 hours. Whether you could drop the rental car there depends on the company you use. You'll have to check, but AFAIK the only company with an office convenient to this plan is Hertz. If you do this, keep the car while you sightsee (to hold the luggage), then turn it in and catch the train. I would keep the car until Rome.

For me, your plans involve too much driving over 3 days.

I recommend you learn about Limited Traffic Zones which have been established in all of the towns you list:

https://www.italybeyondtheobvious.co...with-ztl-zones

Jean beat me to just about everything I was going to say, but to synthesize: you don't need a driver; vineyard visits are not like the ones in California where you can drop in, so visiting an enoteca suffices and obviates the need for a designated driver; too much driving in such a short time; learn about ZTLs.

You might be able to hear Gregorian chants at the Abbey Sant'Antimo near Montalcino. However, the last time we stopped there, the chants were a recording, and I believe since that visit the majority of the monks have been reassigned/relocated.

You could visit the Abbazia di Monte Oliveto Maggiore on the way to/from Siena, but you'd have to do some research to plan this day around the hours the monastery is open and the schedule of the chanting. It's a huge property, and there's a lot to see, so you could spend some time there and that would be taking away from your time in Siena.... Choices, choices.

I'm so sorry to hear about Sant Antimo Abbey! I was going to suggest it for chants. The actual monks were doing them when I was there. I went both there and Monte Oliveta Maggiore with Luca.

Of course, as noted, you can drive yourself, but since you asked about a driver, you have the information and can decide. I was by myself and didn't want to drive, so it was a good option for me.

Thank you for the suggestions. Our plan is to rent a car in Florence in the AM and drive to The Rosewood. If early check in is not available, we would either drop our bags with the hotel and drive around Tuscany or change into our swimsuits and enjoy a leisurely day around the pool (weather permitting). I was thinking of a car hire/guide for our 2nd full day in Tuscany. Our third day could be spent relaxing and/or exploring ourselves with our rental car at a more leisurely pace. We will have 2 full days in Tuscany and hopefully the better part of our arrival day if we can get out of Florence earl in the AM. I am concerned about our drive thru Orvieto as we will have luggage that will have to stay in the car which I hear is asking for trouble. Another possibility would be to return the car to Florence or somewhere closer to Val d'Orcia/The Rosewood and take a train to Rome and a day trip to Orvieto from Rome via train on another day. I have looked at the maps and have read trip reports but still don't have a grasp of Tuscany to Rome with a day trip to Orvieto.

Personally, I think the car theft warnings are a little overblown in most situations, which is not to say it couldn't/doesn't ever happen. But it's the most common type of theft where I live in the U.S. and has never happened to us in 40+ years of traveling in Europe. I think you do what you would do at home. Put everything in the trunk, don't leave things visible that advertise your visitor status (like guidebooks and maps) and don't park in some remote corner of the lot.

I wouldn't drive the car all the way back to Florence just to turn it in. Siena, Chiusi, Orvieto are options with train service to Rome. Or drive to Rome.

We had a rental car in May that we picked up in Florence (by the airport) and used for Tuscany. It was very easy and we
were able to explore the areas that we wanted. On our last day we drove to Orvieto for exploring and lunch before returning the car to the airport in Rome. This worked for us because we were flying out the next morning.

Monte Oliveto Maggiore has Vespers at 6:30 PM every day, with Gregorian chants. There website has a horrible translation into English (done by Google), so I'll just offer the Italian version:
https://www.monteolivetomaggiore.it/...gia-monastica/

A lot of it is easily understood. The most important words are "feriali", which is weekdays, and Saturdays. "Festivi", is feast days (Sundays and major religious holidays, which Google translates as "lively"). "Messa" (plural messe) is "mass". (Google translates it as "harvest".)

At the Monastery of Valserena (Cistercian nuns) all the liturgical hours are sung and are open to visitors. Probably the most convenient would be Vespers at 5:15 PM and Compline at 7 PM. They don't have an English page.

https://www.monteolivetomaggiore.it/...gia-monastica/

Sometimes Gregorian chants are in Italian rather than Latin, and I don't know about these.

There are other monasteries in Tuscany where the liturgical hours are sung, but in my experience, there are sometimes only two or three elderly tone-deaf monks singing. I'm pretty sure these two have a fair-sized choir, but I can't swear to it.

Regarding wine tastings, yeah you can do it while you're in Florence, at enotecas, as suggested.

If you really want to visit Chianti and wine taste, there are bus tours which leave from Florence, though I don't think you drink enough that you couldn't drive. However, that way you don't have to take any time out of the 3 nights in Val d'Orcia.

Of course there's wine tasting places in Montalcino, Montepulciano, etc. Last July most of them were in the 15-20 Euros range. I drove so I didn't partake.

Lot of the scenic places in Val d'Orcia are away from the well-known towns though.

For instance, you have scenic belvederes in Pienza peering out to rolling pastures to the south of town. But there are some agriturismi in that area which have views of Pienza rising above the rolling pastures which is an even better view. I didn't stay in any of them. Instead, I found a few spots with turnouts to pull your car over and was able to take some panoramic shots, including flying my drone over it.