Where to base, 4-5 nights in Tuscany

Hello! I'm feeling overwhelmed trying to find the right area and accommodation type for our first visit to Tuscany.

We do not want to stay in Florence and are absolutely willing to rent a car (not sure where we would pick one up). We will be coming from Rome by train and heading to Venice afterwards.

Would like to be in a country setting, but close enough to access some restaurants in the evening and convenient to visit/do the following:

Florence - 1 full day

San Gimignano

Siena?

Wine tasting

A cooking glass

Our budget: moderate. Willing to spend more for a something special (ie: winery property, a view, etc)

Thank you so much!!



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After cancelling our 2020 Italy trip, I've just booked a trip for spring 2022. We fly into Venice in late April and will be in the country for 21 nights before leaving from Rome. I've booked accommodations online but everything is cancellable so I'd love to know you suggest any changes to my itinerary. And I have a few questions. Any input would be much appreciated as I've never been to Italy!

Here's what I've booked:

3 nights Venice - Wander, see Doge's palace & St. Mark's Square

3 nights in Sirmione, Lake Garda - explore Roman ruins, drive around lake, maybe boat trip to Isola del Garde

3 Nights in Florence - Museums & sights. Rent car when leaving & drive to Montepulciano via Chianti.

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Does this look like a good number of days / nights in each place?

Also, I have a few other questions... From Venice to Sirmione - Would I be better off to simply take the train from Venice to Desenzano and rent a car there, meaning I could drop it at the end of my Sirmione stay and not pay one-way charge? Or rent a car in Venice and drive to Desenzano? And when we leave Montepulciano to go to Sorrento, am I better off dropping the car in Chiusi and taking train from there to Sorrento, or driving back to Florence & dropping it there, taking the high-speed traing?

Or should I re-order the whole trip, driving from Venice to Sirmione and then to Montepulciano, then take the car back to Florence, spend 3 nights there and then train to Sorrento?

I've noticed that a lot of accommodations are booking up already for next spring so if my itinerary isn't logical, I want to switch it around now while there's lots of options. I know there's plenty of time for booking cars & trains, but does the order make sense? Thanks in advance for any input!!

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