Advice on Tuscan hilltowns itinerary

Old Jul 3rd, 2015, 09:37 AM
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Advice on Tuscan hilltowns itinerary

I will be in Italy for 2 weeks in early October and I am seeking advice on an itinerary for our time spent in Tuscany. Our current itinerary has us in Venice for 3 nights, 5 nights in Rome, 4 nights in Tuscany (hilltowns), 1 night in Florence. Should we take one night from Rome and add it to Tuscany?

Which hilltowns do you recommend spending our time in? As of right now, the main places we want to see are Siena, San Gimignano, and Montepulciano. Where else would you recommend, and how would you draft an itinerary? I'm not sure where we are going to stay yet, but we would like to stay in an agriturismo perhaps. We will be renting a car. I've heard that visiting 2 hilltowns per day is recommended, but geography is not my best subject so I'm having trouble figuring out which hilltowns it makes sense to see together based on their location. Can anyone recommend an itinerary for us including which hilltowns to see and what you recommend doing there? I feel like I've read so many different posts/trip reports that the hilltowns all sound the same at this point so I'm having trouble narrowing down the choices!

Thanks!!
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Old Jul 3rd, 2015, 09:53 AM
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Have you been to Florence before - if not spend an extra day there - the three hill towns you have are some of the best - don't forget Umbrian hill towns like Assisi and Perugia - larger hill towns like Siena but really neat IME.
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Old Jul 3rd, 2015, 10:01 AM
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Should we take one night from Rome and add it to Tuscany?

This would depend entirely on your interests. I myself would probably take one night from Tuscany and add it to Rome. I'm very interested in Roman antiquities, and hilltowns to me are interesting mostly for specific things, such as a museum or a church, that I might want to see there.

Several of my favorite Tuscan hilltowns are Montalcino, Pienza, and Sovana.
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Old Jul 3rd, 2015, 10:34 AM
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And I would take one night from Rome and one from Tuscan hill towns and add it to Florence. It is really hard for others to advise you Each of us has different likes and fond memories, many of us from many trips to Italy. I love Florence and used to love Siena but our last trip to Siena was a disappointment. I happen to prefer the Chianti area, including San Gimignano, to the Pienxa area.

If you plan to choose a base to visit hill towns, first you have to decide what towns to visit and whether to focus on the north or southThe towns you have mentioned are all worthy.
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Old Jul 3rd, 2015, 10:49 AM
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If you're interested in the Renaissance, and specifically in Renaissance art, you would need more time in Florence. If not, half a day would be fine. Just wander the streets, go to Piazza Michelangelo, and stay away from the museums.
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Old Jul 3rd, 2015, 11:19 AM
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Thank you for the replies! I am not an art lover so I think one night in Florence is all we'll need. Does anyone have a suggestion of what order to see the hilltowns in?
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Old Jul 3rd, 2015, 12:37 PM
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It is not about order--it is all about location for your base. I feel 4 days is adequate- I would give Siena a full day, San Gim. and Volterra another day, and Montalcino and Pienza a third day. Look at the location for Fattoria Tregole near Castellina as a good central base for that mix. Use the 4th day to see the Chianti region to include Radda, Gaiole, and Castellina.

First, get a good guide book on Tuscany so you understand the geography.
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Old Jul 3rd, 2015, 03:55 PM
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I would not stay in the Chianti if my top 3 sights in the Tuscan countryside are Montepuliciano, San Gimignano and Siena. I would pick an agriturismo nearer Montalcino/Buonconvento, just because I like the scenery much better.

One of the reasons that all the hilltowns sound the same in Tuscany is that, to a large extent, they were all built around the same principles to serve certain needs. The most famous ones for tourist usually have some unusual feature that draws tourists -- but it worth reading as to what that is to find it if you consider it worth the drive to go there. That said, the great majority of towns in rural Tuscany, including the ones never mentioned by tourists and even ones not on hills, are truly charming and very often have lovely works of art and architecture and fine shops and food.

So I suggest you not be too concerned about fulfilling a mandate to visit 2 hilltowns per day. The very greatest attraction of scenic Tuscany is the scenery. If at all possible, try to spend at least some time in Tuscany NOT going to recommended hill towns, because that way you have a chance of encountering the local Italian life of Tuscany that still exists is some places not crowded with tourists all seeing the same recommended 2 hilltowns per day.

If geography is not your stongest subject, count it as an advantage in Tuscany if it gets you away from checklists and crowds and means you end up exploring where other tourists don't go. Nobody ever go so lost in Tuscany they couldn't find their way back again.
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Old Jul 4th, 2015, 04:11 AM
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Excellent advice from both Bobthenavigator and sandralist.

I have sort of a hard time with the idea of a hill town itinerary.

You pick the places you want to go from a guidebook or Bob's suggestions. You find lodging in the middle of them, and an agriturismo as sandra suggested is an excellent idea, and you drive around looking at these places and the places in between them. It is a hub and spoke system, and fortunately you can't drive very fast because the journey is as good as the destination.
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Old Jul 4th, 2015, 02:32 PM
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I'm not an art lover either but I love Florence - have only visited the Uffizi once - I love the old lavish churches and the ambience of place like Oltarno - the old district on the west side of the Arno. and the Boboli (sp?) gardens and Pitti Palace - the Belvedre Michelangelo overlooks all the neat ride tiled roofs on Florence laid out far below - the veg and food market - an old-world type place - the Ponte Vecchio - I'd take a night out of Rome and put in in Florence perhaps but heck there is no need to 'have to stay' in a town that does not appeal to you.

But Florence is not all art - the Catehdral is the original model for Gothic churches - having a huge dome rather than flat roofs of Romanesque architecture - a seminal thing in church developments - climb up to the dome itself.
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Old Jul 5th, 2015, 09:58 AM
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Thank you for the suggestions! I am only going to Florence because in my previous posts it was suggested that I take the train from Florence to Milan on the day of our departure rather than from Rome to Milan. (We are flying into and out of Milan.) Otherwise, we would probably skip Florence entirely as there are other places that interest us more. I think we will keep the number of nights we had originally planned for Rome and Tuscany. Would an agriturismo near Siena make the most sense? I will also look into ones near Montalcino. Thanks!
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Old Jul 5th, 2015, 01:43 PM
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We traveled from Florence to Milan on our departure day, but we kept an eye on possible train strikes, and we had an emergency budget in case we would have had to find a different way to get to the airport that day. Most people here wouldn't recommend doing what we did.

Lee Ann
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Old Jul 5th, 2015, 02:24 PM
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We loved our stay in this agriturismo near Pienza. Individual apts located within a larger villa. Hosts are outstanding, breakfasts to die for, location phenomenal.

http://www.fontebertusi.it/en/

One day we visited Montalcino and the abbey of Sant'Antimo. Beautiful stained glass. As we entered this beautiful monastery, the monks began chanting and the light was streaming in through the stained glass (the way you see in the movies). It was magical.

I agree with the others above: one full day for Siena and combine San Gim and Volterra another.

We also loved our stay in San Gim. You could do Montalcino/Sant'Antimo as a day trip.

We stayed a full week in this region and were busy every day. Just beautiful!
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Old Jul 5th, 2015, 02:43 PM
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But Florence is not all art - the Catehdral is the original model for Gothic churches - having a huge dome rather than flat roofs of Romanesque architecture - a seminal thing in church developments -

The Duomo of Florence can't be the original model for cathedrals like Wells, which is unquestionably Gothic and about 100 years older. Even in Florence, the Basilica of Santa Maria Novella is older than the Duomo, and is definitely Gothic.

And how many Gothic cathedrals have huge domes?

Italy on the whole was not terribly enthusiastic about the Gothic style.
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Old Jul 5th, 2015, 03:08 PM
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If you are only going to Florence to catch a train to Milan airport, have you considered Bologna instead?

(Actually, what I found most puzzling about the duomo of Florence was to suggest it isn't above all a great work of art.)
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Old Jul 5th, 2015, 04:00 PM
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San Gimignano and Volterra are indeed justly famous, but the Val D'Orcia is our favorite area of Tuscany for quintessential hill towns. Montepulciano-Pienza-San Quirico-Bagno Vignoni-Montecchiello... Etc. . Also highly recommend the Abbey at Sant'Antimo if you visit Montalcino. And lunch and a garden tour of La Foce is a magical experience in nice weather. If interested in ancient history, be sure to thoroughly explore Chiusi nearby. You can see the only Roman catacombs in this part of Italy if you arrange in advance (Catacombs of St. Mustiola)
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