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Four nights in Tuscany

I’d love some advice about where to stay in Tuscany. We have four nights in early April after having spent four nights in Florence. We will be renting a car, probably in Florence, and returning it there before taking the train to Venice. We’d want to do a wine tour, see historical sites along with scenery, and we like mingling with locals whenever possible. We could do two nights in one town and two in another or all four in the same town. Friends who have been to Italy have recommended Siena, Lucca, Chianti area. Too many choices!
Thanks in advance!

Posted by
6471 posts

Any one of those would be great—what I find helpful is to start researching accommodations and see if that helps one stand out (of course if you are not a kind of person who is very fussed about where you stay, ignore this advice). Next, read what the specific places of interest are with an hour or so radius around each place. You want to have scenic drives but not have a long slog each day.
I strongly suggest all four nights in one place, and it sounds like a loop through Chianti would be just right.

Posted by
1864 posts

I don't think Lucca is the Tuscany you're probably looking for. The area of Lucca, Pisa and surrounds are flat and have good train access but are not the rolling hills of Tuscany from photos and film. If you do go to Tuscany a car will generally be a burden so I would stick to trains.

Siena is definitely worth visiting but I would take a day or two to explore the town itself and then rent a car for a couple of days if you want to explore the area. Siena is a tourist center and a good town to take a wine tour from if you want to do that. Italy has really strict drunk driving laws that just got stricter so I would not drive and do a wine tour yourself unless you have a designated driver.

Around Siena Castellina in Chianti, San Gimignano, Volterra, Greve and Rada in Chianti are all popular wine centric options within a hour or so of driving and there are many other small towns scattered around if you just want to explore.

Generic rental warnings: Get an International Driver's Permit IDP for every driver before you leave the states, read up on ZTLs in general and then specifically before visiting any small, touristed town. Allow time for narrow roads and getting lost or thinking you're lost when you're actually fine. Take a sense of humor and add at least 25% to Google time estimates for all these things.

Enjoy, rural Tuscany is as beautiful as advertised.

=Tod

Posted by
3500 posts

Lucca is best visited as a day trip by direct train from the Florence SM Novella station: https://www.trenitalia.com/en.html that takes 1h 45m. You may need to add a night to Florence and take a night away from the Tuscan hill towns.
You could loop through the Chianti wine region (Chiantigiana) the morning you rent a car in Florence: https://lovefromtuscany.com/scenic-drives-in-tuscany/. I highly recommend sleeping in Siena’s old town. Siena is best in the evening hours after the day trippers leave.
Do drive the Val d’Orcia which features rolling hills, well-maintained brick spacious farm houses with many different landscapes. Montalcino is the place to take a wine tour and Pienza’s old town is worth a stop. Montepulciano is a good place to drink more wine and eat dinner.

Posted by
1808 posts

Lucca is best visited as a day trip by direct train from the Florence SM Novella station

Our experience was that two nights in Lucca were wonderful, and we could have added a third night to work in a musical performance. With a limited number of days, the transit time back and forth is more than a bit of a waste.

Posted by
283 posts

We stayed in Lucca for 2 nights on our way to Cinque Terre, but I agree - I don’t think it’s the Tuscany you’re picturing. A good plan might be to pick up your rental and head toward Siena. If you stay on the western side of the main road (RA3?) you will drive through rolling hills, vineyards, and olive groves. You can easily stop in Certaldo, San Gimignano in the way toward Siena. Stay somewhere in the Siena area. From there you can explore Siena one day, the Chianti region one day, and even a bit south to Montepulciano, Pienza and/or Montalcino region. If you’re headed back to Florence to fly out, RA3 is like an interstate and an easy 1 hour drive back. There’s so much available within day-trip striking range, I’d be tempted to stay all 4 nights in 1 location and not waste the time of moving locations.

Posted by
2144 posts

As much as we enjoyed Lucca (spent 3 nights there) I agree that what you are looking for is Val D'Orcia, the Tuscany with rolling hills, Cypress trees, vineyards, olive groves, hilltop villages, etc. We spent 3 nights in Siena, and I think that would be the perfect place to stay for 4 nights. Siena is beautiful; the cathedral is stunning; the Campo is magnificent! And lots of great restaurants.

Some towns to visit while in Tuscany: Pienza, Montepulciano, San Gimingnano, Volterra, and don't forget the small village of Monteriggioni. This was not on our radar; it was recommended by our hotel, and we loved it! Very special. And not crowded at all when we were there in May.

I can recommend Hotel Palazzo Ravizza, which has a parking lot. Very important if you are renting a car.

A couple restaurant recommendations:
Trattoria Nona Gina
Vivace Restaurant
Quatro Venti

Be sure to book a wine tour/tasting/lunch in advance. We didn't do that, and we were unable to have a wine tour and tasting.