Tuscany Itinerary Help and Ideas

Florence as you already know is the perfect base for not having a car. Another place that might work is Lucca. Pisa would put you closer to places of interest but Lucca is more attractive of the two.
From Siena you can take a direct train to Montepulciano for the day (1h 15m) and a taxi to the city center. Another good day trip option is a direct bus to San Gimignano (1h) but those are the only convenient places to visit by public transportation from Siena that I’m aware of.

Please reconsider renting a car for Tuscany. I can’t imagine not having one to visit small villages here and there. We have visited Tuscany many times and always had a car.
Give Bologna at least one more night, maybe two more.

Completely agree with Suki.
I realize having a car and driving is always last choice but honestly it is so very needed to really experience and enjoy the Tuscany countryside. Public transportation is just very limited anywhere other than Siena and Lucca and even from those 2 towns you are limited.
Driving in Tuscany is easy and delightful. Pick up car as you leave Florence.
Where will you depart to UK from?

I think with no car I’d base in Lucca but not really plan to day trip much, you are sort of too far west and north there. I am sure there are cooking classes there, you can bike the walls, etc. sort of a quiet place with no major must sees if it’s own.

With a car base in Val d’Orcia —Montepulciano or Pienza or an agriturismo in that area.

Haven’t been to Bologna yet but would give it at least another night. Might be great place for cooking class, supposed to be foodie city.

Thank you all for the replies and definitely some things to think about! We'll have to look more closely at Bologna and see if we want to add a day or two there. Especially since we would love to explore the food scene.

MaryPat-we haven't gotten that far in terms of where else to explore. Open to ideas! :-) Looks like a few names from others to check out. Like I had mentioned previously it would be great to have a base to operate from so we don't have to change hotels every day or so.

Christine H-Undecided on departure to UK. We are meeting family in either Cork or Dublin, so will want to fly into either city. Thinking we leave Bologna, head to the countryside in Tuscany somewhere and finish in Florence and then fly out from there? Open to other options though.

Yeah, we haven't closed the door on a car, I just would prefer not to have to hassle with the whole process of a car and when we go wine tasting someone missing out on it because they're driving. Of course it sounds like there's hassles with not having one too! LOL. Sound like we'll have to have some further conversations on this topic.

Food and wine will be our primary focus in Tuscany, so places that would allow us to focus on that out of Florence and in the countryside. Thanks everyone for some great ideas....keep them coming! :-)

We started in Bologna this past September (2021) and then headed to southwestern Tuscany for a week. We enjoyed it so much, we’re going back to the same place for more this coming fall, and then including Florence, which wasn’t part of the 2021 trip.

For Bologna, at least another night or two would be well worth your while. We discovered phenomenal restaurants, and also took a day-long Parmesano-reggiano/prosciutto/balsamic vinegar tour. The area is also home to Lambrusco wine, and there are far superior versions there, compared to the cheap Riunite from my college days in the 70’s!

In Tuscany, just inland from the Etruscan Coast, there’s a real gem in the Bolgheri/Castagneto Carducci area. This is the heart of “Super Tuscan” wines, and although we didn’t participate in any of the tastings at the many wineries, or tasting tours that can be easily arranged (and allow everybody to taste, without the need for a designated driver), we did lots of sampling at local enoteccas.

Our lodging was particularly special. There are lots of options in the area, but we stayed at https://cookingintuscany.cc/casa-toscana/ . Chicca, an architect who renovated the old farmhouse, created two apartments in the floor above her ground level home. She teaches cooking classes there, in person. She’s also been teaching classes online throughout the Pandemic, which is how I learned of her and her place. She can do wine tours, two. Each apartment has 2 bedrooms, and a washer. Many hill towns in the area are worth exploring. Other than a few Germans, you'll not find the throngs of tourists that go to other parts of Tuscany.

Given your particular interests you might want to check out the "Things to do" pull-down menu on TripAdvisor. There are a number of wine tasting tours, cooking tours, and day trips from both Florence and Siena ... which would be good bases in order to allow you to cover the prettiest parts of both Chianti and the Val D'Orcia without the necessity of renting a car.
Basing in Siena for a few nights would allow you to enjoy the place in the morning and evenings, ie without the day trippers that fill up the town between 9 AM and 4 PM. And if you change your mind about booking a car it's pretty easy to rent one from one of the concessions near the train station. That way you could explore some of the hilltop villages that are really only accessible by car. Montepulciano and Pienza are two excellent suggestions.

Edited to add: for accommodations I suggest starting your search on Booking.com. Their cancellation policies are usually pretty liberal and they have some very nice options that might suit the 3 of you. I'd strongly suggest booking a place with A/C for your July visit.

Thanks Cyn and Robert for the great info! Looked the the place you stayed Cyn and it looks great, but doesn't look available for when we'll be there. All these responses give a great start for me to look at and research more. I did notice a couple of places (including yours Cyn) have pretty liberal cancelation policies, which is nice. One was 2 weeks prior the other 1 month prior. Will make me feel better knowing we can book and not have huge risk this far out.

Thanks again for all your input!

If you use Siena as your base, you have easy access to these towns. They are easily accessible by bus and train. Some towns I've combined with others. (B=bus, T=train)
Siena-Colle di Val d'Elsa ( B 30m)-San Gimignano (B 35m)-Siena (T 1H05m)
Siena-Montereggioni (B 18m)-Castellina in Chianti (B 30m)
Siena-Radda in Chianti (B 55m)
Siena-Buonconvento (T 28m)-Monteroni d'Arbia
(T 12m)-Siena
Siena-Rapolano Terme (T 37m)-Asciano Mont Oliveto (T 10m)-Siena (T 26m)
Siena-Sinalunga (T 53m)
Siena-San Quirico d' Orcia (B 50m)
Siena-Pienza ( B 1H05m)
Siena-Certaldo (T 39m)

Many wine tours are available from both Florence and Siena.

That said having your own transportation can’t be beat.

Jed, glad my info was worth a look, and I’m sorry she’s already booked for when you’re going. I believe the “Cooking Club” that’s developed from her online cooking classes is going to be a big source of lodgers in the future.

One of her cohorts in producing the online classes is an American named Jed. Small world. 😊