Florence/Siena/Countryside - 2 nights in each?

If you have three nights outside Siena and Florence by all means spend them in one place and use it as a base. If you just have three nights total, choose one place to spend all of them and don't day trip.

The Tuscan hooligans are really a short distance south of Florence for the most part. I too suggest finding a centrally located agriturismo or B&B and do day trips from there.
I like outside of Poggibonsi, San Gimignano or Certaldo as a central location. There are hundreds of farm stays in the area.

At most split your stays in 2 towns, that being Florence and Siena. Florence is a blockbuster of sights so maximize your time there. Start early end late then bus it to Siena. Then see and enjoy Siena then bus it easily and to close by villages of Pienza and Montepulciano or San Gimignano. Busy days but easily done, I have done it.

my ideal spot would be a countryside B&B or hotel but then I'm stuck eating in the same restaurant each night since we won't have a car. hence, florence and siena as options. otherwise i would be doing florence and the countryside and skip siena.

Rachel, looking back at your previous posts you've been sort of all over the place with your plan:

Our plan is to fly into Florence for 2 nights, then spend 4 nights in
the Tuscany countryside and then 4 nights on the Amalfi coast before
heading up to Rome to fly home.....We are staying near Montalcino
(Castello di Banfi) for four nights in July and not renting a car.

I think I agree now that we should rent a car and drive ourselves to
and from the cities and then just take cars when we want to tour
wineries or are going places where it’s hard to park a car.

If we don't rent a car when staying in Tuscany, is there somewhere
better to stay so that we have better access to restaurants for
dinner?

I am torn between spending the whole 4 nights in either Montalcino or
Montpucliano or spending one night in Siena on our way down south and
hitting Sam gimignano and volterra. Is it worth spending one night
there? Also we aren't renting a car so we will have car service drive
us the whole day.

Am I crazy to try to spend 2 nights in all 3 spots (Florence, Siena,
countryside) in Tuscany rather than just picking one or two?

We want to wine taste and relax and not worry about driving.

I think you're going to have to narrow down depending on personal priorities and style? Two nights in 3 locations would be too much moving around for us. Lounging in the countryside isn't high on our list of things to do in Italy, and we're very independent travelers who wouldn't want to be tied to hired drivers to get around but prefer not to rent cars. My interest in Renaissance art and architecture demanded serious time in Florence but those are our priorities not yours.

If you want to take a lot of day trips with public transport or hired drivers, I think you're going to want to base in more urban versus rural locations. You also need to consider how you usually travel: are you comfortable changing locations often or prefer to unpack and settle in for awhile? And then there's what you want to do with your time? I'm seeing mentions of "walking around", dinner and some wineries but no interest in historic sites, museums, basilicas, etc. It's FINE if you don't care about seeing those things - again, this is YOUR trip - but if you do, you don't want the one full day, 1/2 day (or less) you allotted for a location to be the one a lot of those things are closed or it pours rain. Longer stays offer some flexibility to work around stuff like that.

Without a car, any desire to move around a lot in Tuscany will most certainly invite travel horror stories. You can't possibly know what "ideal" means until you experience it. One's fantasies during the planning stages of a trip are rarely what you experience in reality. I visited Florence several times before I ventured south to Siena. IMO, Siena takes more work to visit because it's a city that requires a steeper learning curve. There are smart ways to approach a visit to Siena and not so smart.

If you don't speak some Italian, getting around by public transportation can feel daunting. It can be very frustrating trying to find someone who speaks English to explain why the bus or train has not shown or will not come.

Smart planners build in time for the unexpected when visiting Italy. If you try to run around too much and depend on public transportation schedules to get around, you may be shocked to learn how little time you have left to actually experience the place you're visiting.

Smart planners build in time for the unexpected when visiting Italy. If you try to run around too much and depend on public transportation schedules to get around, you may be shocked to learn how little time you have left to actually experience the place you're visiting.

It's hard for me to imagine trying to see the Tuscan countryside without a car. If renting a car is out of the question, then I suggest splitting your time between Florence and Siena and do a small group wine tour from either.

Enjoying " the serenity of a countryside castello with a pool overlooking the landscape" can't be done in a night or two. This dream would take a week to do it justice.

Logistics can really cut into time available each day. Taking the train from London to Paris is only a few hours travel time, but checking out, getting to the station, going through customs, the trip itself, getting a taxi to our B&B and checking in took a full day.

Expect the unexpected. We used an agriturismo as our home base, but on the advice of our hosts, we took the 40 minute bus ride to Florence instead of driving. You have to know which bus to board. We got on the right bus, but since there were only three of us left, the driver decided not to go to the terminal. We had to figure out fast where we were and how to get to where we needed to hook up with our tour. We had 25 minutes. Thanks to some very helpful folks, we caught the right local bus and got to Piazza San Marco with 4 minutes to spare!

Rachel,

Trying to do three two night properties would waste an inordinate amount of time. You might be better served using a property in Florence.

This one is on the edge of town, has beautiful gardens and a big plus,
A free shuttle into town.

http://www.villaagape.it/en/index.php

To see the countryside, use some of the small group tours. More of these are available in Florence than in Siena. There are also some easy day trips you could easily do by train.

Staying in Florence will facilitate easier transport by train to your next location south of Rome.

thank you everyone for your helpful replies!