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Town suggestion for overnight stay in Chianti

Husband & I are taking our first trip to Italy at the end of April, and staying in Tuscany, with Montecatini as our home base. It was booked through another travel company-Sorry RS! Trip comes with a car & suggested day trips. We would like to avoid the back & forth driving from Montecatini to Chianti region and want to combine 2 days with an overnight stay. The towns we want to visit in Chianti are Greve, San Gimignano, Siena, and Val d'Orcia. Would really appreciate suggestions for relatively cheap but decent hotel in, or near, one of these towns.
Additional trip info and more questions: flying in/out of Milan. Day trip to Florence-definitely by train. Day trip to Lucca/Pisa-is it better to go by train or car? Should we drive & possibly leave the car in Lucca for the day? I think I read that there is a bus that goes from Lucca & drops you off right at the Leaning Tower in Pisa, as opposed to walking a mile from the train station.
One more question-is it worth taking A7 to drive past Genoa on way from Milan airport to Montecatini, just to say we were there, or is it more of a hassle? We will be stopping in Parma on our return to Milan, where we are staying overnight before morning flight home.
I thank everyone in advance for any & all suggestions!

Posted by
1585 posts

Karbar - Cortona, Pienza or Arezzo will be a good base in Chianti for overnight stay to explore the nearby towns. A day trip to Lucca/Pisa is more convenient by rail. However, you can also drive and park in Lucca (https://www.discovertuscany.com/lucca/where-to-park-in-lucca.html) and take train to Pisa.

Accommodations in the area:

http://www.anghelhotels.it/relaischiostrodipienza

http://www.viaroma25arezzo.it/

https://www.villapienza.it/

http://www.cortonacharmingaccommodation.com/villabaldelli/

Posted by
4105 posts

Day 1. Drive to Greve in Chianti 1hour.
From Greve to San Gimignano 45 minutes.
Visit late afternoon after the crowds leave.
Dinner in San Gimignano. Then sleep in one of these towns.

Certaldo, Colle Val d'Elsa or Poggibonsi. (This last will be the most central to the places you want to visit)
All will have access to the Firenze-Siena freeway.

Day 2. Travel to the Val d'Orcia first then head to Siena. Then back to Montecatini. 1 hr. 25m.

Please be aware of driving restrictions in Italy.
You will also need an IDP which is a translation of your drivers license, available at AAA

Edit .

Posted by
872 posts

Read this about driving in Italy and restrictions involved [ZTLs]; do not leave anything of value in a car when parked:

http://driventoit.blogspot.com/

Some Gate 1 travelers regret having a car, with town and city centers off limits. Be sure the agency is not Maggiore; get the full insurance. Pisa and Lucca definitely by train [also Pistoia for the market Wed and Sat AM]. You would be overnighting in Malpensa before flying home. We like the Villa Malpensa with its very good restaurant.

Posted by
30 posts

We had a very nice stay in Greve, but I also like Panzano and Radda a lot. I don’t think you can go wrong with those. Yes, drive in Tuscany, but try to avoid the larger cities, driving is very stressful and signage is often too small to read. Definitely agree with above, full insurance is a must. Parking is uniformly a challenge. Try not to circulate looking for parking. There are many, many street restrictions like ztls and one-ways. In Greve you can have opposing one way streets that meet each other. Going around the block can mean going around the entire town! Greve does have a visitor garage, it’s tights and crowded, but very handy. Be prepared to walk. Visit Montefioralle. Enjoy!