Tuscany in May

We rented a Villa in the Chianti region for May. Planning to take day trips and explore. Visited Tuscany in 2017, with a tour group, did Pisa and Florence and the beautiful town of Orvieto ( in Umbria). What towns in Tuscany, would you highly recommend?

Will you have a car?

Bagno Vignoni's my favorite spot in the Val D'Orcia

Hi Christine - I'll be doing it all by car and staying away from Siena/Florence - two cities that I've already stayed within.

There is a terrific hotel right below the walls of San Gimignano [10 minute walk], comfortable with a very good breakfast and parking on site. The Relais Santa Chiara. See it on booking.com. Dinners in town or up the street at Graziano

Have a nice trip. May a great month.

Jeff-

We’ve been to Tuscany once- Florence, Siena, Montepulciano w/day trips, Assisi

I am putting together our 2nd trip now for this Sept and will do this:
Florence 3, Orvieto 2, Pienza 3, Volterra 3, Lucca 3

I found this hotel in Volterra, seems to be about the only place that worked with a car. Just at the wall, parking, good for day trips.
Hotel San Lino
http://www.hotelsanlino.net/en/

Spending some time in Greve as a home base appeals to me.

We used Castello id Verrazzano as our home base and loved it. It was convenient, quiet and inexpensive. Their tour and food and wine tasting is well worth the afternoon it takes. The grounds are gorgeous and we made a day of just wandering around and doing the tour.

From Greve, you can hop on the Chiantigiana and ramble through the charming towns of the region. San Gimignano and Volterra are a lovely one hour drive away. Lucca is ~1.5 hours, an easy day trip, if you can tear yourself away from Verrazzano's amazing breakfast.

Greve seems like a good place for a base - though getting in and out of Chianti is always a bit of headache as the roads are so bendy. you could think of staying somewhere just west of Chianti (I'm thinking Colle val d'Elsa, Casole, Poggibonsi) so you can head into the Chianti but will have an easier drive when going toward San Gimignano and Lucca.

Poggibonsi is a strange place - it was a train hub during the war so was heavily bombed, but the centre is still beautiful and the old fortress on the hill is very interesting.

If you're staying in Lucca, the drive into the mountains is worth doing - they rise up to around 6000 feet and have some great villages and restaurants. Pietrasanta is worth seeing too - it's the city of marble sculptors as all the mountains there are made of white marble - the same marble that Michelangelo carved his David from.

Also, consider Pistoia - it's often ignored but quite charming. Have a great trip!