Suggestions for independent travel after Best of Tuscany tour

The Chianti towns between Siena and Florence are wonderful places to base yourselves.
We have spent four vacations in that area. Look at Castellina , Radda, Panzano, Greve, and Gaiole
for possible stays. I highly recommend a rental car for Tuscany and Umbria and can’t imagine how you’d explore the areas without one.
We have never stayed at an agriturismo so can’t help with one of them.

Can you be talked into the car? The driving in Tuscany is rural and really not stressful. If it is an option, it opens up a whole new world.
I've been in Tuscany in May and seen few other tourists, but it was not in towns on the train line.
Near Lucca/Pisa, I had San Miniato on my list for a recent trip (unfortunately cancelled). Barga up in the mountains is nice, but since you are headed to Rome, I would go south. Massa Marittima is lovely. Pitigliano is striking, not off the beaten path but in a beautiful setting and interesting. I think Siena is well connected by bus, but you'd likely have to book tours for getting out of town with ease.
If you really do not want to drive, then check out the NYT article this week on towns in Umbria by train--Orvieto, Perugia, and one other I forget.

I’m considering the Tuscany tour for either May or September. Since I just got home from Berlin, Prague & Vienna tour + independent travel, I need to relax and think it through. Initial thought is if I go in May, spend 5 days or so in Rome and several in Florence pre-tour and a week post tour in Venice, Padua and maybe Trieste. If I decide on September I’d reverse the order: Venice, Padua pre-tour; then (back to) Florence, Rome post-tour. South to north in Spring; north to south in Fall.

Since I won’t drive in Europe anymore, I want easy train routes between stays on my own. Skipping Venice isn’t an option; it’s my favorite city in Europe.

Enjoy your trip!

Look at Castellina , Radda, Panzano, Greve, and Gaiole

Suki, are these accessible by bus or train? I'm not trying to hijack Ruth's thread, but we were thinking of spending a week or so in Florence next year, but given the many reports of crowds, I'm rethinking that. And my question would also be relevant to Ruth, since she'd rather not drive.

I can add a vote for Radda as I spent a delightful day there last mid-September at a wonderful winery. I was on a Staycation in Florence with Adventures with Sarah. No crowds and very pleasant weather at that time of year.

I am also taking Tuscany tour in April. I plan to take a train from Lucca to Milan and take day trips from there. Still researching. There are so many places to see in Italy and this is my 4th Italy tour!

You might look at the island of Elba. I was on the first Tuscany tour in April '22 and I see that Elba will no longer be on the iitinerary for 2024. When we arrived the hotel said we were the first Americans that had ever stayed there. (I find that hard to believe). The crowds were very manageable. Personally, I visited the Cinque Terre after that tour and the crowds were fine, but that may not be the case these days.

We did the Best of Tuscany tour a month ago; yes, Florence was very crowded. The guides we had were very helpful with that, but definitely be prepared to be on the streets with lots of tourists.

Having said that though, it was really nice at sundown; I remember walking back from a restaurant in Florence at about 6pm, and the streets were really nice. If you want to have a truly spectacular Tuscan meal, which will be a couple of blocks from your Florence hotel, check out Cafaggi; your guide will probably walk you past it. We had our best meal there--highly recommended.

When the tour ended in Lucca, we took a train to the Cinque Terre--I don't think I would recommend that. It was super-crowded, and not what we were expecting. The train was easy though, and if you don't end up with a car, the train is simple to navigate and very reasonable.

Most of the places you'll go are off the beaten path; Siena is the only other decent-sized city you'll visit, and it wasn't bad at all; Volterra is a tourist site and was very busy, but still not so bad, and we enjoyed it.

Our tour went to Elba; it was very nice, but rain kept us off the beach. We walked through the small town square after dinner one night--not a big place, not sure whether I'd say it's worth a day, but there weren't a lot of tourists and it was easy to navigate.

You'd almost certainly need a car if you wanted to stay in the Tuscan hills; there's just not much out there, and driving would be a pleasure anyway--the countryside is truly beautiful. I'm not one who would want to drive in the UK, but I'd gladly drive in Tuscany; traffic is light, the roads are pleasant, drivers aren't crazy like they are here in the US.

Our favorite spot, and I'm guessing your tour willl go there, is Gargonza; wow, what a great place to stay--I'll say no more and let you be pleasantly surprised!

If you have a car, you'd probably enjoy any of the many small towns that dot the Tuscan countryside; your tour will bypass Pisa, which is apparently super-crowded--not sure it would be on my list if I were returning. We talked about how much fun it would be to find a small quiet village and spend the day there; they're all over, and could make for a great relaxed day.

If we were to do the tour again, we'd probably spend a few days in Rome, which is always worth a return visit. Having been there before, we'd skip some of the main draws (the Colosseum, the Vatican, and the Pantheon), but there are so many other places that are incredible and well worth a visit. For example, consider going to see the Baths of Caracalla, which we toured and which were almost completely empty, and which were fascinating. We'd also love to see the Appian Way, which we didn't get to see when we were there last year.