Solo Travel in Northern Italy - Not sure what to do, and suggestions appreciated

For me, I would spend the last six nights in Venice.

It would be unusual, I think, to find tours originating in tiny places like San Gimignano. On any given day, there probably wouldn't be enough people wanting to take the same tour. Most people staying there probably have their own wheels.

You might look at Tours by Roberto, a company often recommended on this forum. I believe there are small-group tours originating in both Florence and Siena. I don't know whether there are still spots available on those tours for August. It seems as if an awful lot of people are traveling right now.

There are also commercial tours (perhaps using big buses) that combine San Gimignano and Volterra (definitely worthwhile), I believe.

It's often possible to get to a small town by public bus from a base like Florence or Siena. The problem comes when you want to see multiple small towns on a single day. That is often frustratingly difficult if not impossible.

If you're willing to drive, that would make it easier to see a bunch of small hill towns over the course of just a few days. I know nothing about the drop-off situation, though.

You don't have to give up your dream of seeing some of rural Tuscany, but it's possible you won't be able to do so as efficiently as you hoped unless you rent a car. The freedom a car would give you would likely outweigh the time required to return it to the pick-up point. (I say that as a big fan of public transportation who has never rented a car in Europe.)

Thank you so much. I am thinking that yes, I should hire a car. Would you think Montepulciano would be a good base, or would you recommend somewhere else?

Please don't be anxious. Italy is a wonderful place to travel and everyone likely will be warm and welcoming even to a solo traveler. I am sure you will see that during the first part of your trip the tour. As you will be on your own I think you would enjoy staying somewhere like Siena, where you you can return each evening to the same place, a small hotel or B&B, and in the evening enjoy the passagiata, etc. Maybe in a smaller neighborhood rather than the tourist main drag. But if you want to stay in smaller town Montepulciano is lovely. And don't dismiss how easy it is to get a rental car even if more expensive than relying on public transport. I searched AutoEurope.com a random Thursday to Monday picking up in Chiusi and dropping in Florence and while there is a $65 one way additional fee it does give you all the freedom of your own wheels.

It strikes me that even if you are 100% comfortable driving on the right-hand side of the road, you will not be able to see much of the scenery while driving and will have a challenge driving yourself without another person to be your navigator. We have driven a LOT in Italy and my husband is an excellent driver (and can read and speak Italian) and he is often frustrated that he can't appreciate the view and has not enjoyed the few times I have not been navigating. Also, in August the parking spaces outside of the hill towns will be quite full and so will the popular towns. Someone else driving you around solves many problems.

I think staying in a less touristed part of Siena and going on tours to the towns you want to see is a great idea --- look at Tours by Locals and Airbnb Experiences for someone who can give you a personalized itinerary. This is the apartment we enjoyed staying in the last time we were in Siena: https://www.airbnb.com/rooms/21406684?guests=1&adults=1&s=67&unique_share_id=f8a9c4e2-d00c-48e2-a61f-09f419f76c55 Lovely helpful host, close to the train station but still within the old city walls, nice neighborhood, nice views, and 15 minutes walk to the Campo. Might be too big for you, but there are other apartments around there. Staying in Siena, you can wander in the early morning and the evening without being in the crowds of daytrippers, then do your tours during the day.

Consider, also, visiting other Tuscan towns that are slightly off the most popular tourist track, such as Volterra and Massa Marittima and Tarquinia. Consider, also, simplifying your life by skipping the Cinque Terre --- it's pretty, but will be mobbed in August.

Have you been to Venice? If not, I would sure give Venice 3 or 4 of your extra nights, employing the same strategy of staying far from the heavily touristed areas.

Be sure where you choose to stay has AC.

Your anxiety will subside, I promise!

Consider using a map site or app (google/apple) and placing markers on villages you are considering for a visit. Then see if there is a logical, larger city to hub from. Being transitory while on vacation will wear you down quickly. Figuring out the buses in Italy can be relatively easy and you can view the scenery as well.

Unfortunately, CT has become a mosh pit, especially in high season. I agree with others that have suggested Venice for several days instead.

If you are flying out of Venice, then maybe arrive there several days prior to your flight. Venice, for all the hype, is a very intimate city. The third time you walk into a bar, you will be greeted, as so many tourists make fleeting visits.
From Venice, many other towns are reachable by train. Verona, Padova, Vicenza, Treviso and Bassano del Grappa in the mountains.
Add to that the lagoon islands, especially Burano and Torcello, and you have many options.