Mamma_Love

Hi all! Now that we've decided to rent a car, I have to do more research and we only have about 12 days until we leave for Italy. These are all day trips from Siena.

Are these itineraries realistic? Is there anything that I should add, or in your opinion, leave out?

Day trip 1: Montepulciano, Pienza, San Quirco d'Orcia (maybe just a short stop), Montalcino

Day Trip 2: Monteriggioni, Poggibonsi, San Gimignano, Volterra, Massa Marittima (Maybe just short stops for the first two)

Day Trip 3: Radda, Greve, Gaiole, Castellina

Day Trip 4: Arezzo, Cortona

Also, actually doing all 4 of these trips may not be possible, I am thinking of cutting one of them - which one would you cut if you had to?

Thanks fir any advice you can provide.

uhoh_busted

Figure you will see two or three towns a day. From noon until 3 or so, places shut down (except for restaurants so that you can have a leisurly lunch.) That means, no churches, no theaters, no shops, nada will be open. So plan to have a nice easy looooooong lunch. Be somewhere picturesque (not hard to find in Tuscany) and enjoy.

bobthenavigator

A good start--you have been paying attention. Your day one will be tough since you should include the 2 abbeys that day. Do Montalcino, the abbeys, and Pienza this day. Try to drive via Asciano going or coming.
Day two is too much--Massa is just too far. Forget Poggibonsi, it is a commercial town, and do the other 3 starting in Volterra.
From Siena, I would make day 4 as Cortona first and then come down along the west shore of the lake to Chiusi and end up at Montepulciano--which you had to drop from day one.
Hope this makes good sense. Have fun !

Marilyn

As always, bobthenavigator is right on the money.

Massa Maritima was a day trip by itself for us, with a stop at San Galgano. It's too far to include with almost anything else.

Monteriggioni can be seen easily and in its entirety in 15 minutes, unless you want to have a meal there (several good restaurants).

If I had to cut a trip, it would be Arezzo and Cortona, simply because they require the most driving from your central location.

Another rather charming town between Monteriggioni and San Gim is Colle di Val d'Elsa (in case you have extra time, hah!).

The best advise I can give you is to leave a little extra time to wander some back roads. You will be rewarded with beautiful landscapes and perhaps an adventure.

Mamma_Love

Thanks for your advice! I really appreciate it.

I've been giving this a lot of thought and here are the towns that I feel I must see, perhaps you can help me tweak it a bit to make it all fit.

Montalcino
Montepulciano
Pienza
San Gimignano
Volterra
Of the towns in Chianti, I really don't have a preference on which at this point, but sufice it to say that wine tasting is priority. (Also a big reason for Montalcino and Montepulciano topping the list.)

I think I will cut Arezzo, Massa Marittima, and possibly Cortona because they are just a bit to far compared to the others (...always need to have a reason to go back).

Our schedule is tight. We will be driving to Siena from Venice, and I figured we could see a few places in Chianti along the way.

The next day, I thought we go to Montalcino, Pienza, and taking your fine advice Bob, see Asciano. If we can fit Montepulciano, great, otherwise I will make that another day.

Next day would be possibly Cortona and Montepulciano.

Last day would be Arezzo and San Gimignano on our way to Florence for the last few days of our trip.

Any further advice? Is this still too much? Are lingering lunches and dinners enough to make this feel more relaxing and less busy?

Also, I must add, that I want time to wander around Siena, but figure that we can do much of that after touring for the day, before and after dinner (maybe some in the early morning too). Will I actually be able to see anything in Siena? My primary goals there are to wander around the neighborhoods, see the Duomo, and have coffee or gelato or sip wine in the Campo.

Thanks for your insights so far, any help you could provide in addition would be truly appreciated.

Marilyn

"Last day would be Arezzo and San Gimignano on our way to Florence for the last few days of our trip."

I assume you mean Volterra and San Gim?

This sounds a lot more enjoyable, Mamma Love. Do Volterra in the morning and have dinner in San Gim so you can get some feeling for the town when the hordes have departed.

Mamma_Love

Opps! Yes, I meant for the last one to be Volterra and San Gimignano.