Itinerary for mother/daughter trip through Tuscany - summer of 2025

We stayed a long weekend in Florence and then rented a car and moved to an agritursimo outside of San Gimignano and Certaldo. We had a kitchen so we could cook our own italian foods. Virtually every farm in Tuscany has apartments and rooms for rent as a secondary source of income. And they're all perfectly good places to stay.

We visited a number of hilltowns from there--staying in one place. Our favorites were San Gimignano and Volterra. We also liked Orvieto which is where we dropped off our rental car. Rome via train is just 70 minutes from there.

I would suggest you look into staying in no more than two places while you're there. The distances are not that great, and it's just easier not to pa k up and move. Lucca is a good place to stay for those wanting to see the Cinque Terre and Pisa.

I think that I might fly into or out of Venice and then out of or into Florence so that you could squeeze it in the trip. (Fly into one city and out of the other) Look for multi city airfare.

Montepulciano is in the Val d’Orcia. Montalcino, Peniza and Montepulciano are all fairly close together. I enjoy them all, but Montalcino is my favorite. You can day trip to all of them from the others (30-45 minutes of each other). If you are interested in doing a cooking class in the area, my favorite was at Podere Il Casale.

No rental agencies in Cortona. You can rent one in Arezzo, or in Florence before heading to Arezzo. You should have a car to do 3 to 7, or even 2 if you plan day trips from Arezzo (such as Anghiari, Lucignano, Poppi/Casentino Valley, Loro Ciuffenna.

I would do Florence as last. Basically you could rent a car upon arrival and head to Arezzo (about 1 hour drive). If your flight arrives late then spend the first night in Florence then pick up the car the next morning. Spend the last 3 nights in Florence before your flight home. You can return your car in Lucca and take the train or you could drive the one hour to Florence and return the car at the airport. The Lucca-Florence freeway ends at the airport and returning the car there at the airport car rental center is very easy.

If you follow the above plan (pick up in Florence and return in Florence) you might save on one way drop off fees. I heard that since the pandemic they started charging higher one way drop off fees, before the pandemic they never charged me for that.

Re: the rental drop off fee - I just looked at my statement from last October and it was €18 at the Florence airport. I picked up in Venice.

If you have 20 days- then that means 19 NIGHTS- if you count your trip in NIGHTS you’ll get a better picture of the overall flow.

You could fly IN to Venice- spend 3 nights here with a day trip to Vicenza. Venice is a great place to get over jet lag and it is much easier to fly IN to Venice than OUT of Venice.

Train to Florence and pick up your car this day (at the train station locations- you’ll have more options here for automatic, etc. than in a smaller town)
I wold not pick top car and drive on arrival day- since you are already leery of driving in Italy, no point adding more stress!
And honestly- driving in Tuscany is easy. You will be parking outside the towns so avoiding ZTLs is pretty easy.

Head to Val D’Orcia.

I would pick 2 bases in Tuscany.

One in Val D’Orcia- Pienza (flat) or Montepulciano (steep) for 4-5 nights
We love both and have stayed in both with a car but found Pienza easier to access and park with a car. If you need recommendations for hotels with parking and easy access, let me know.

Or you might want to stay at an agriturismo - with a pool- it will be very hot!

From this location you can day trip to Arezzo, Cortona, Rocca del Leone, Montalclno, Monticchiello, Bagno Vignoni, etc.
(Volterra and SG are too far as a day trip- about 2 hour drive- see these towns from your 2nd Tuscany base.)

Second base- Siena or environs 4-5 nights. Again make sure your hotel has easy access/parking- ask for recommendations here.
Siena is lovely at night when day trippers have left.
From here visit Volterra, SG, Chianti towns, etc.

You could drop car here in Siena once done with day trips then train to Lucca (change in Empoli and probably Pisa)) or just drive to Lucca to drop car. We did this last year- easy.
Lucca- 2 nights or 3 nights if you want to day trip to Pisa.

That still leaves 3-4 nights. Train to Florence and end there. Florence itself should get at least 3 nights.

Fly home from Florence.

Reposting on this thread as we've changed our plans a little after taking into consideration advice here and the fact that we're going June/July of 2025, which turns out to be a holy year. We have narrowed things down to the places we'd most like to see, in the order we think will maximize usage of trains when possible, and have picked 2 bases for the main part of the trip as recommended. We'd appreciate your feedback on this revised plan.

Florence 6/19-22, then train to:

Perugia 6/22-27, use as base to do day trips to Orvieto, Spello. *Pick up car here and drive to:

Castiglione del Lago 6/27-28, then drive Val d'Orcia to agriturismo in Central Tuscany.

Agriturismo 6/28-7/5, use a base for day trips to Sienna, Cortona, Arezzo, maybe more. Drive to:

Volterra 7/5-7/7, then drive to/drop car at:

Lucca 7/7-7/10, then train to:

Florence 7/10-7/13. Note: if we end up flying into Milan, then may add on a day or two and stay first/last night there to make it easier.

How likely are we to run into issues getting an *automatic** at the Perugia Airport rental car location? This is a must, so will determine the order of things a bit if we need to go elsewhere to get the rental.

Please let us know your thoughts, thank you

Any responses would be most appreciated, especially regarding the likelihood of getting an automatic car in Perugia. That may require us to change things a bit, so please let us know your thoughts.

I would just go ahead and contact an agency in Perugia, or call AutoEurope. Always best to get it straight from the horse's mouth!
I have never had a problem getting an automatic and have not always rented at major airport locations. Sometimes I have had to put in a request and gotten it confirmed at a later date.