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Tuscany in October

My husband and I will be spending 2 weeks in Italy this coming October, our second trip to Italy in two years. We will be flying in and out of Rome (from Boston). From Rome, we'll be traveling immediately to Florence, and plan to spend 4 nights in Florence and then 4 nights in Siena. While we're in Siena, we think we'll rent a car to tour some hill towns -- probably Volterra and possibly San Gimignano for day trips, but we're open to suggestions. We'll spend our final 4 nights in Rome...because, well, it's Rome and we loved Rome when we were there last year. But that leaves us 2 nights between Siena and Rome to try somewhere else. We're thinking of possibly staying in Montepulciano for the two nights, driving there from Siena. We'd love some recommendations on this. We're not big on scheduling every minute, and like to walk around, explore and get to know an area...and, of course, sample the local cuisine. We're thinking of dropping the rental car in Orvieto before we head to Rome, so we'd also like some thoughts about renting the car in Siena and dropping it on Orvieto. Thanks!

Posted by
1566 posts

With a car, visit Siena as a day trip from Montepulciano and stay there for 6 nights instead. For my tastes, Sieana itself is too big as a base with a car but we are all different fortunately. From Montepulciano, lots of pretty villages within easy reach in Tuscany and Umbria, and if you have the car on route to Rome you can catch Civita and Orvieto on the way.

Admittedly, San Gimigano and Volterra are a fair hike from Montepulciano but if you leave early enough you can catch both on the same day, and it makes for pleasant driving on the back roads. I've read that there are also day tours from Florence to San Gim and Volterra.

Posted by
135 posts

We did not rent a car for seeing Tuscany. We did a private tour with Hills and Roads and it was the best decision. We told our guide Angela what our interests were and let her do the rest. Six hours is minimum and you can decide as you go how long and where. We followed all her suggestions and each one was a winner. We ended up wth an 11 hour tour not by her coaxing but ours. It was worth every euro. She gave us the history of the places we visited and answered all of our questions. You can't get this by driving from place to place.
Besides she was delightful.

Posted by
135 posts

We did not rent a car for seeing Tuscany. We did a private tour with Hills and Roads and it was the best decision. We told our guide Angela what our interests were and let her do the rest. Six hours is minimum and you can decide as you go how long and where. We followed all her suggestions and each one was a winner. We ended up wth an 11 hour tour not by her coaxing but ours. It was worth every euro. She gave us the history of the places we visited and answered all of our questions. You can't get this by driving from place to place.
Besides she was delightful.

Posted by
8097 posts

We have over the last 35 years twice spent a week in a Tuscan hill town and five years ago we spent two weeks in Montepulciano. Every trip was wonderful. I think the best choice is to rent a place in a hill town with parking and use it as a base. In the day you can do day trips to the area (Montepulciano was fabulous for that given its location) and then in the evenings you have a town with restaurants and bars and lovely walks. You don't want to drink and drive at all in Italy.

Most rentals are by the week Sat-Sat in Tuscany but you an sometimes when it isn't high season get shorter stays or odd weeks. I love having a car and being able to visit towns, parks, gardens, monasteries etc .

Siena is a nice place to spend a couple of nights but it is so large that getting in and out of town to visit other towns in Tuscany is more of a chore. There are lovely hotels with parking within the walls though and it is wonderful in the evening.

Posted by
1091 posts

I think that I would also move the 4 nights from Siena to Montepulciano. Then you could take the rental car to Orvieto to drop and spend two nights there before Rome. I do love Siena, but I love the Tuscan countryside more. It fits our pace better.

Posted by
906 posts

I think you have to go to Umbria for a couple of nights. Here is what I want you to do, or at least consider.

Stay in Orvieto. Day trip to Assisi, Montefalco, and Todi. If you want more try Deruta for ceramics, Perugia for a University, abd Spoleto for a castle.

Whatever you do enjoy it.