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Need help with our 4 days in Chianti

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I am really struggling to design a plan for our 4 days in Tuscany (3 full and 1 partial). It will be our first time to the region (husband, self and daughter 14). We are interested in views, photography, food, wine and shops with local crafts but not interested iin spending time in museums. We will have already seen Florence and will see Pisa after we drop the car off. We will drive from Florence to Siena, spend one night, then mid day then next day head to Villa Vignamaggio just outside of Greve for 4 nights.

I know we want to see Volterra and San Gimignano one day. QUESTIONS: is there anything place else we could/should work into that day for a brief stop to stretch our legs that might have charm quaintness or great views,craft shops or food/gelato?
I thought we would go to Volterra first see it and have lunch, then on to San G in later afternoon see it and maybe have a apperitivo before heading back to Vignmaggio? Any shop or restaurant suggestions? Daughter would like to go to torture museum and if I read correctly both towns have one if so which is better?
QUESTION: my daughter's birthday will be during the Tuscany part of the trip so anything you can think of that might be special to see/do in Chianti esepcially not too far from Greve area?
QUESTION:Could we see Greve, Radda and Gaiole in 2 mornings? Should we plan to see them? Given our interest any suggestions?
QUESTION: would Montepulciano and Pienza be a doable day trip from Greve or just too long?
QUESTION: Any recommendations for dinner spots or craftmen's shops in the Greve/Radda etc... area? We don't want to eat every dinner at Vignmaggio.
I would welcome any other thoughts.
Sorry for all the info, just trying to provide as much as you may need to provide the best help.
Thanks in advance.

Posted by
336 posts

I can amswer for one or 2 questions.
-Montepulciano is 1:45 minutes from Greve. So if you leave at 9, you’ll be there by 11. It’s small, you walk some streets, spend time on piazza grande, maybe even eat a panini and have a fabulous spritz while looking at the marvelous medieval buildings. Just beside the chruch, you can buy wine and visit the Contucci winery. When looking at the church it’s on the left.
Let’s say you leave at 2pm, take one of the most beautiful road in all europe, the sp146 and you’ll be in Pienza 20 minutes after. So you are there by 2:30. This village is smaller than montepulciano, you can spend a few hours, buy some pecorino cheese take picture of the sceneris in the back of the village.
So you can leave at 4:30-5.
From there, you say you like photography, some real tuscan classics are on that road going from pienza to san quirico d’orcia: cappella di vitaleta is photographed by everyone. Just google that name. Also maybe the most famous picture is the one taken of Podere belvedere(google it as well). The best spot to shot it is about 1.5-2 miles before san quirico. You’ll be at the end of the day when the light is at it’s best.
-close to volterra/san gimignano(try to finish the day there as there is a lot of tourists before 4pm) you can go the minuscule village of Monterigionni. It’s small but very charming, will take you an hour maximum.
-i have not visited the chianti region enough to help you out.
- as far as craftman products, Volterra is known for alabaster products.

Posted by
1150 posts

The country roads of Tuscany can be very twisty, curvy and take much longer than you would account for on a straight two lane highway. Gaiole is a destination of such roads. I’m not sure it would warrant the car ride for what you will find there. Radda is also really small.

While you could certainly do everything on your list, it kind of defeats the whole purpose of being in the Tuscan countryside. You will see a lot, spend a ton of time in the car.....but the purpose of Tuscany is to find “il dolce far niente” (the sweetness of doing nothing). The property where you are staying is absolutely gorgeous! I would encourage you to spend some more time there, relaxing by the pool and enjoying Greve. They have an incredible town center with tons of shops and fantastic restaurants. One of the oldest butcher shops in Italy is there too.

Posted by
2591 posts

hey taywin
as april mentions spend time at your place and the area around. the 'famous butcher" Dario Cecchini and his shop is located in panzano in chianti, creative butcher and showman, plays rock and roll, along with a restaurant across the street. read up on him at panzano.com or dariocecchini.com
Near Lucca is the town of collodi, birthplace to pinocchio. there is a park, beautiful garzoni gardens at the villa and butterfly house, a cooking glass "chefpaolo-cookingtours.com" with half day lessons. also some are in tuscany or having a private chef at your place, ask the owner of your place. enjoy and have fun on your holiday, la dolce vita. happy travels
aloha

Posted by
1 posts

Hi. Im from Finland but Ive been zig zagging Tuscany ten times and been several times in Chianti area. Sure you can visit Montepulciano and Pienza and Moltacino in one day. But start early and come back for dinner.

Oneday roadtrip with unforgettable scenery along the Crete route, beautiful hilltop villages and through magnificient countryside starting from Arbia (east side of the Siena, starting from higway Siena- Bettole SS73, exit Taverne di Arbia.) Now you drive through area called Crete, winding road number SP 438 to - Asciano. Really beautiful open countryside, rolling hills as far as you can see. From Asciano to Monte Oliveto Maggiore ( famous Abbey) road SP451 and from there to Montalcino ( home of Brunello Montalcino wines. Lots of wineries in the area, where to visit and have lunch or even take a cellartour for example Tenuta Barbi)

Montalcino to famous Abbey Sant Antimo road SP 55. and from there to Monte Amiata (old volcano continue along the same road SP 55, drive through Monte Amiata to Castiglione di Orcia SP 323 and go on to Bagno Vignoni. From there take a road SP 53 and turn to a road SP 18 towards Pienza so you drive through Val di Orcia valley to Pienza. From Pienza road SP 146 to Montepulciano.
From Montepulciano to Torrita di Siena ( first SP 17 then turn left to SP135 huge downhill road and very nice scenery) . From Torrita drive to Bettole. If you like shopping there is a Outlet Village just by Foiano. If not take a Highway back to Siena. Bettole to Siena takes about 50- 60 minutes.

This initerary takes a whole day. Start early and have lunch either in Montalcino or go to some winery for lunch. There are plenty of them near Montalcino. For example Fattoria Barbi http://www.fattoriadeibarbi.it/en/the-taverna-dei-barbi/ Or you can drive from from Montalcino to famous Taverna Banfi . https://castellobanfiilborgo.com/en/dining/la-taverna.php This is a magnificient place alltogether. https://castellobanfi.com/en/

If you want to go and see cellars in Montepulciano, the only one I`ve seen is Avignonesi. I highly recommend this one as well. https://avignonesi.it/en/hospitality. Number one in Montepulciano. Super nice old cellars and tour.

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