Tuscany day trip - rent car or small group tour?

Having done both self-driving and small group tour (we went with Roberto of Tours by Roberto) I recommend the small group tour. No worries about ZTLs, speeding, navigation and lots of insights from a local perspective. The camaraderie of other tourists is nice, too, once in awhile when self-touring.

You’re going to have a ball!

We love the freedom of our own car at our own schedule…..not a tour person. We did this same thing you are and based in Montepulciano and drove around the delightful towns in Tuscany…..stopping when we wanted and staying as long as we wanted…..like you driving in an unfamiliar country does not bother us…..but sometimes just getting out of the gated parking lots without knowing the language can be a challenge!

We base in the small Chianti towns between Siena and Florence and find it wonderful to explore Tuscany on our own. We have never had a problem with a ZTL in many years of driving all over Italy.

Laurel and Jane presented good arguments for both options.

We stayed in an agriturismo just outside Greve for a week. We had a rental car and explored the region and had a great time. We never had problems with ZTLs and we strictly observed the speed limit, since there are automated speed checkers.

I think you'd do well with either choice, but here's some things to consider. If you want to try the wines of the region, I'd favor taking a small tour, especially one that does a food and wine tasting for lunch. That way you can sample as much as you want without worrying about driving, especially since more than one glass of wine would put you over the limit and penalties are stiff. A small tour would also be nice if you are gregarious and enjoy being with others. While we prefer to travel and tour alone, we took some Walks of Italy tours that are limited to no more than 12. We had great groups and enjoyed visiting with our fellow travelers, especially since it was just a short time.

Be aware that all of the places you listed that you want to see are pretty far from Florence, so far it would be impractical to do as a day trip. You would be better staying a couple of nights in Montelpulciano on the way to Rome. The other option is to explore closer to Florence. There's lots of great hill towns between Florence and Siena that are half as far away.

Tours by Roberto has day tours for 110euros/person
RS recommended
https://www.toursbyroberto.com/

I was just going to post the same info. If you go to that webpage and click on Contact Us, you'll get a pop-up that shows the prices. I haven't taken any of Roberto's tours, but I have certainly read a lot of positive comments about them.

Click on Calendar and then Calendar of Availability to see which tours are scheduled for which days and how many empty seats there are. There are departures from both Florence and Siena; that's something you'll need to pay attention to. Also, tours do not run every day. Perhaps some additional tours will be added in September if demand strengthens.

I am not big on "tours" but it depends on personal preference. In general, a few days in Tuscany (as opposed to downtown Florence) call for a rental car for the best experience. But, in a way, you are saying that you want specific multiple towns in one day AND that you can get them with a small group tour product. That is a go-ahead for your plan. In a way, you are saying 'One day for Tuscan hill towns.' (Not a judgement, just reading your post ... ) I have nothing against "included lunch", but sometimes it is a time waster - worth inquiring not how artisanal it is, but whether it's geared to "getting back on the road!" We've been on some big-bus tours where omitting the lunch gave us an extra hour or more Free Time.

Without an art history degree, three days sleeping in Florence might be enough for the art and architecture there. Note that many Tuscan towns have important frescoes and so forth. Some towns, like Siena especially, but also small towns like Cortona, have some important paintings in museums. Just FYI. I suppose energy and walking-mileage is a factor for some couples. Advance ticketing recommended for high traffic attractions in Florence and Siena.

For the most part, we are dedicated to independent travel. However, you say you are not comfortable driving in another country. The roads in Tuscany are narrow, winding, and hilly. There are multiple opportunities for getting lost. The driver must keep eyes on the road, not enjoy the scenery. Then, there is the issue of finding parking. In your circumstances I recommend doing the tour.

The roads in Tuscany are narrow, winding, and hilly. There are multiple opportunities for getting lost.

That's the charm! If you think Tuscan roads are narrow, you should try driving single track roads in Scotland! I drove and had no problem seeing the scenery, we just pulled over frequently.

I've been researching a wine tasting day trip from Florence, too. The Tours by Roberto look interesting but I noticed that there is a 30 euro additional charge for food and wine tasting. I emailed our hotel and they recommended Keys of Italy. Their Chianti tour is 119 euros per person. That covers a small van, wine tasting and lunch. It's a shorter tour which appeals to us. We're not sold on spending 8 hours in a van on a tour. Has anyone had any experience with Keys of Italy?

Thank you all for your insights. As some smart person said "two heads are better than one"

Your answers were all helpful, even though it was a matter of personal choice type question. I knew going in I could go either way - tour or car rental. For the record I am completely comfortable driving on hilly, winding roads in a foreign country, with scenery so beautiful that I have a hard time keeping my eyes on the road! Also love to meet new people and would enjoy leaving the driving to someone else. We are not big wine drinkers, especially during the day. The thrust of this exercise is to see the towns, people and scenery. The tours all seem to be geared towards wineries, although with enough digging I'm sure I can find something to my liking. I had checked Tours by Roberto - he has received the Midas touch from RS and is booked up for my time. (pretty well booked period)
I posted back in February for itinerary advice and I thought it was good "don't try to do too much". Hence 4 days in Venice, 5 in Florence & 5 in Rome. Jane & DougMac have now conspired to put thoughts of Montepulciano in my head. The little voice in my head says slow down and enjoy Florence but reading and looking at all the pictures, Tuscany has had an exotic pull on me for years now.
The question now becomes - stay in Florence 5 nights or 3? I am embarrassed to have such problems!
One thing I'm sure of, a good time is guaranteed!! Luckily I do have the means to return, and will, as long the good lord allows and the creek doesn't rise.
Cheers, Dan

Since you are spending time in Rome and Venice, why not zen out in the hills for all five days? I'd find all three of the big three in one trip a bit overwhelming. This is the year people really seem to be getting back to traveling, and all three will likely all be mobbed. I'd save Florence.

Instead of spending five nights in Florence sleep there for three nights then take a direct bus to Siena (1h 15m) and sleep in the old town for two nights. After your first night in Siena take a taxi to a car rental company then drive along the scenic Sienese Crest Road to Montalcino, Pienza and Monepulciano before going back to Siena.