Winging it in Tuscany-Are we crazy?

That's prime tourist season. No way I would do that without a reservation. You'll spend most of your days trying to find some place that has availability.

Go for it.

Are you saying that you need to plan driving around?? Or reserve hotels in those towns??

Don't expect Germanic efficiency in Italy. Slow down and enjoy.

we are spending a week at an agriturismo near Siena. There are too
many towns and not enough days, and really we just want to drive
around to different places everyday based on the recommendations of
the owners and guests at the b&b where we are staying.

This is exactly what we did when we stayed at an agroturismo. I had a list of towns I was interested in, based on reading I'd done. Every morning at breakfast I'd haul out the map and list and we'd decide ( with input from our host) what we'd do that day. We were relaxed about it. We didn't see everything, but that's fine. We didn't make any Restaurant reservatioms- just browsed the menus of interesting looking places until we found something we liked - we weren't interested in "fine dining". It was one of the most relaxing weeks of our trip. And every night when we returned to the agroturismo, our host would ask how our day had gone. And we'd smile.

i say lucky u. JUst go witn theflow. San Gimi, siena, assisi, cortona, Volterra, so many options so little time. Just relax and enjoy. I will be in Sicily this summer
Another great italian destination.

I am re- reading your post, as well as the other responders. If your sleeping arrangements aren't in question, then absolutely wing it with your day plans! Some of our best memories and experiences were the unplanned, unexpected and even accidents. I misunderstood and thought you were still looking for lodging also.

Wander. Get lost. Stop in the random towns. Definitely take recommendations from your b&b owners! Enjoy. 😉

You can find accommodations on the same day on any given day in Tuscany, even Florence. Obviously the sooner you book, the more the available choices and the better deals.
The key is to have internet connection (with smart phone, tablet, etc.) so that you can search along the way the day before and go to a website like Trivago, Booking, etc. and quickly see what is available on the day you need.
I have never found problems finding accommodations in Italy even on the same day. But the sooner you can book, the more choices you are available.

My understanding is that you are staying in one place in Tuscany, but not planning your daytrips ahead. This is absolutely fine. We spent three weeks in Greve-in-Chianti with no specific plans, but a general idea of some places to visit. We planned only a day or two in advance depending on what we discovered was available. Go for it!

Your heading is confusing. Myself and I think others assume you meant not having lodging reservations.
Assuming you just mean decide what to do on a given day, that makes perfect sense to me!

Sorry, we do have accommodations, but we have not planned any activities or towns the week we are there. It sounds as if we should be ok, without any plans. Thanks for your help.

I think it sounds fabulous!

If you have accommodations booked, then you're set. Just be cautious about where you are and are not allowed to drive/park that car, OK?

We went the opposite time of year during the low season and did pretty much what you plan. We had a rough outline of what we wanted to see and do, but nothing, other than a trip to Florence, was locked in. I think you'll be fine. Talk to your hosts. If you want to visit Sam Gimignano and Volterra, I suggest an early start to make sure you can get parking.

Make sure you plan a late day for Siena. The town is magical in the evening. Get your hosts to make a recommendation for dining and plan to come home late.

I'd love to be able to spend 32 days in Italy! Have a great time!