Driving Itinerary in Tuscany

Jul 21st, 2015, 09:34 AM
Original Poster
Join Date: Jan 2003
Posts: 161
Driving Itinerary in Tuscany

We will be staying at an agriturismo near Vaggio in Tuscany for 7 nights in early October.
Have never been to Tuscany outside of a 5 day trip to Florence.

Would like to ask for help with daily itineraries built around lunch in the following places – San Gimignano, Pienza, Montalcino, Monticchiello, and San Quirico.

In addition to visiting for lunch and exploring, we would also like to include Pienza, Siena, and a tour of Val d’Orcia (thanks to Stu Dudley and others).

Would like to be back by 7:00 as I have trouble driving at night and would also like to have some relaxing time inbetween.

Need help in planning the days from the experts.
Gynna is offline  
Jul 21st, 2015, 09:53 AM
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Are you locked into your agriturismo reservation or are you willing to substitute other hill towns for your excursions? Many of your target towns in the val d'Orcia are about 90 minutes from Vaggio -- and that is if you spend most of your time on the autostrade. Once you get to Tuscany, I think you will that is not really fun to spend 3 hours on the high-speed autostrade each day. So if you really want to explore the val d'Orcia, you should consider relocating to an agriturismo near one of the towns you mention. If you pick one near Montalcino, then it makes it easy to include San Gimignano as a day trip from there.

If it is not possible to undo your reservation in Vaggio, then what you might consider is getting up very early one morning and driving to the val d'Orcia and try to visit all 4 towns you mention in that area in same day, and pick one of the towns for lunch. You will need to be done with your touring by 5.30pm, however, so if you want to spend any time exploring each town, you sill need to get an early start.

That way, you can visit San Gimignano on a separate day, but also explore the pretty areas and charming small towns that are closeer to Vaggio itself. Some towns you might want to consider for lunch and touring are Loro Ciuffena, Radda in Chianti, Montespertoli, Sant Andrea in Percussina (home of Machiavelli) and many castles in the area.
sandralist is offline  
Jul 21st, 2015, 10:03 AM
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Also, in October, there are usually truffle and chestnut festivals near Vaggio:

sandralist is offline  
Jul 21st, 2015, 10:12 AM
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Thank you, Sandralist, for your suggestions. Will look into the small towns you mentioned for a more relaxing day. For a variety of reasons, we will be staying near Vaggio.

Would be willing to spend time on the road each day if we are able to explore more at a slower pace.

Would like to build a daily itinerary around the above mentioned places for lunch to include the other mentioned places.

Need to find out how to visit without back tracking very much.

Forgot to mention that this is part of a larger European adventure so we will not be jet lagged upon arrival.
Gynna is offline  
Jul 21st, 2015, 12:49 PM
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It really sort of depends on how early you hit the road in the morning, and what you consider relaxing.

For instance, if you leave Vaggio at 9am, you could drive to Radda in Chianti in 45 minutes. It's a small town, so stopping by for a mid-morning cup of coffee would give you an opportunity to enjoy the town. If you leave there at 11.15 am, then you could head onward to Montalcino for lunch, which is 90 minutes from Radda. I would be tempted to visit San Quirco d'Orcia after lunch -- but then by 5pm, head back to Vaggio via the autstrade (that's a 90 minute drive.)

On a separate day, drive 30 mins in the morning to visit Loro Ciuffeno for your mid-morning coffee, but then take the autostrade to get to Pienza for lunch (that will be 90 minutes from Loro Ciuffena). After lunch and sightseeing in Pienza, visit Trequanda or Montisi before heading back to Vaggio.

On a different day, try heading to Lucignano for your morning coffee, and from there on to Montepulciano for lunch. Spend the rest of the day in Montepulciano before heading back.

But like I mentioned earlier, that means every day you will be spending at least 90 minutes or more driving the autostrade. If you get any rainy days, it will be even less relaxing. And you will need to get on the road by 9am to make those drives. If you don't head out until 10am, you will need to get on the autostrade right away if you are trying to get to the val d'Orcia for lunch.

That's why I would be temped to take the first nice day you have and go straight the val d'Orcia and see as many of the towns you want to see you can. You can always drive back if you didn't mind the drive and want to see more of the area. But to commit to 3 lunch reservations in the val d'Orcia when you are staying in Vaggio is to commit to a lot of driving. The food and wine is so nice around Vaggio, it could be more relaxing to make just one or two excursions to the val d'Orcia but otherwise enjoy short drives in your neighborhood.
sandralist is offline  
Jul 21st, 2015, 06:29 PM
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I agree that your location is not great for your planned day trips. I have to assume you have good reason not to stay in the Val d' Orcia. But, here are 3 lunches we enjoyed in that region---hope it may help:

The most enjoyable part of the trip for me were the 3 days trips we had planned from our base location in Montepulciano. If you only had 3 days to spend in south Tuscany, and love rural landscapes, small medieval villages, and good Tuscan food, then here are 3 great days for you to consider:

• Montepulciano in the AM, lunch at the wonderful Osteria La Porta in Monticchiello http://www.osterialaporta.it/monticchiello.en.php, and then a tour of La Foce gardens at 15:00 [only on Wednesdays]
Call ahead to book space on her lovely terrace. Be there by 12:30

• Begin in Pienza in the AM, and then drive north via Santa Anna in Camprena[English Patient site] to the charming village of Castelmuzio and here for lunch: http://www.locandadicasalmustia.it/ We discovered Castelmuzio thanks to Isabella Moricciani who was kind enough to show us her spectacular new rental place in the village: http://www.casamoricciani.com/ [ also has 2 smaller apartments].
Not cheap, but this is the nicest place I have seen in rural Tuscany, and well located for exploring much of south Tuscany. End your day with a visit to the Abbey at Oliveto Maggiore after 15:00. Take your camera to capture some spectacular Tuscan landscapes.
bobthenavigator is offline  
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