Help with Tuscany Itinerary
 

DH and I are finalizing our itinerary for 5 days in Tuscany next month. We would love some input into our plans. Any suggestions or recommendations would be greatly appreciated.

Day 1: Pick up rental car in Rome and stop at Orvieto on our way to Montalcino where we will spend the night. If time, we will also visit the San Antimo Abbey.
Day 2: Visit the following hill towns: Pienza, Montepulciano, San Quirico d’Orcia and Buonconvento. (spend night in Montalcino)
Day 3: Tour Siena and then drive to San Gimignano via Monteriggiono to spend the night.
Day 4: We are leaving this day open, some options will be to visit Volterra or return to some of the places we have already visited. Spend the night in San Gimignano.
Day 5: Return to Rome.

Vigorous schedule. You might consider spending an easy day in Sam Gim. Great place to walk around. Have lunch at the Dorando.
Alternatively you can drive to Chanti and enjoy the small cities like Greve or Radda and sample the vino.

Sant'Antimo is not an "if time" sight - it's unmissable if you have any interest in medieval architecture (and you have, given your other destinations). If you don't get to it on day 1, you could substitute it for Buonconvento on day 2 - S. Antimo is the far more important sight!
Day 3, however, cannot work. Siena alone needs more than one day, so there's no way of seeing Siena and Monteriggioni and S. Gimignano on just one day, plus driving. These are in fact two full days.

I think Day 1 is too ambitious, but that depends on where you are flying into Rome from.

You could save Orvieto until Day 5 on your return to Rome day. There will be so much beautiful scenery for you to admire on your way to Montalcino, why not savor it and not have to rush. Keep in mind that it will get dark earlier next month and you want to find your accommodation before dark.

Day 1 - too ambitious
Day 2 - backtracking which doesn't make sense (look at a map)
Day 3 - too ambitious

Too many hotel changes, too little time spent visiting the places/towns on your list.

I suggest just one base for the entire stay.

Snowflake,

The general guideline for hilltowns in Tuscany is: 2 per day. Possibly three IF they are very near each other and very, very small, and IF you can get a very early start! Throw in an abbey if it's in the vicinity.

Reasons for rule: shops shut down for the long lunchtime; lunch is hard to find after 1:30 pm. so you need to do lunch when everyone else is - make res for popular restaurants like Latte di Luna in Pienza. Need to allow time for photo ops along the way or interesting discoveries along the way. No rushing allowed in the Tuscan countryside....

Siena is too large IMHO (and wonderful) to be considered a morning stop, especially with plans to visit two more places before stopping for the night. The lunch break is something to be factored in, really. Too ambitious.

Also too ambitious is Day 1, especially if arriving jet-lagged from the US. Depending on when your flight arrives, customs, more time than you think picking up a car, jet-lag again.

I would also agree with the suggestion pick one base, maybe two, and do daytrips (fewer than planned) from there. Tuscany is not a drive through.

What they all said. Drive to Montepulciano, stay at Locanda di San Francesco. Drive to Siena, and all the other hill towns for day trips. We have done this and LOVED it.

Thanks to everyone for their input. First, this is the last leg of our 3 week trip. We will spend 3 nights in Rome before heading to Montalcino. We took your advice and have booked 4 nights in Montalcino ( we booked in to La Crociona after reading wonderful reviews) and will do our day trips from there.
Dayle, thanks for the advice about 2 hill towns a day. I also read your trip report and have bookmarked it so I can make a few more notes before we leave.
We will also switch our stop in Orvieto to the end of our trip and stop there on our way back to Rome. We won't be in a big hurry that day, just need to arrive in time to drop off the rental car and check in for our last night before heading home.

I hope Montalcino works out for you, but it is remote for some of the day trips you are planning.

Having stayed in Montalcino, I think Pienza or San Quirico d'Orcia are better base towns for southern Tuscany. They are more central and easier to get in and out of.

You could drop your rental car in Orvieto and take the train into Rome. No need then to drive in Rome or make the detour to the airport to drop the car.

We spent our final night in the Parco de Medici hotel near FCO and drive over there in the morning for the plane. Works fine and is relaxing.