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Need help planning Tuscany trip

We have been to Italy once before and visited Rome, Venice and Florence, we saw all the main museums, etc. We are meeting a group from our home town which will go from Venice to Milan over 6 days with tours and winetasting. We are planning on arriving 5-6 days early and would like to go to smaller towns in Tuscany. We did a trip like this in France in 2017, we started in Lyon and drove no more than 1-1.5 hours per day, stopped in a village by noon, parked the car, stayed in a central hotel or B & B. I was done driving for the day. We then walked to the various sites, wine tasted and enjoyed ourselves.

Can we do that in Tuscany? We enjoy seeing some sights like Churches but we are more about food and wine and being in a village or smaller town. I hope to visit some wineries, but will limit consumption.

I am considering flying into Rome or Florence then renting a car, eventually drive or train to Venice to meet my group. Again any suggestions are appreciated.

I have heard Orvieto is very nice, Montalcino, Siena. Appreciate any input on a route and towns to visit. We have been to the Amafi Coast, but not Pisa or Lucca.

Posted by
336 posts

It's indeed the perfect place to do that.
-Orvieto is great, fantastic church as a matter of fact.
-Montalcino of course with divine Brunellos. The village is a nice visit, go on top of the fortress for spectacular pictures, they have also wine tasting inside the fortress. And all around is Brunello world. You will fine dozens of wineries.
-The road, SP146 that goes from San Quirico D'orcia to Montepulciano, going thru Pienza might be the most Tuscan of Tuscan roads. You'll stop every 3 minutes for pictures. And again as you approach Montepulciano, you are in Vino Nobile Di Montepulciano world. Dozens of wineries again. Have a drink on Montepulciano's main piazza. It's fabulous. On the corner of that piazza is the oldest family winery, belonging to the Contucci family for 40 generations! Nice people there. You can take the southern road to go back, going around Monticchiello.
-You can do the Chianti road: Greve in Chianti, Volpaia, Raddi, Gaiole, etc. I visited a big commercial winery there, ricasoli. Great castle, super views, but a huge company, so not as personal. But the castle itself is worth the visit.
-Other villages like San Gimignano(go towards the end of day to avoid massive tourists coming by bus from Florence for a day trip). Then the village is very charming.
-Volterra is another nice village not too far, you can do both in one day quite easily.
-Siena is a fantastic town, with an amazing church, piazza, museum. So much history there. Spend the whole day there, there's a lot to do and see.
Tuscan is heaven for me, period. :-)
Have a great trip and do not hesitate if you have other questions

Posted by
4105 posts

You might fly into Rome, and on arrival train to Orvieto. Get over jet lag here then the next day rent your car from Hertz and start your journey.

Here are some wineries we've enjoyed. Located a short distance from Montepulciano. Newer, very hi-tec Small village about 10 minutes from Montepulciano. Winery encompasses the entire village. Grandfather of Brunello wines. Outside Montalcino. Gaiole in Chianti. Include the Castel and grounds tour.

These last two are a few miles apart. Do a tasting and snack at one and tasting and lunch at the other. Both are very good.

Most of these offer lodging and are a short drive to town.

There are so many wineries in this area, check with your lodging for their recommendations.