In Oct. we are going to spend 3 days in the Chianti region. Which city is best for our home base--Radda or Castellina? We like to stay in a town which has ample restaurants and shops.

If you want "ample restaurants and shops" you might want to go elsewhere. Both Radda and Castellina are very small. Radda has just a few streets, including the main one out of town, and only a handful of restaurants.

What is "ample" to you? We have staying in Castellina twice this year as a base for Chianti and it was a very good location. It is between Florence and Siena, so we daytripped there. However, some would say to spend more time in either of these cities. We visited Radda and liked the town, but it seemed smaller than Castellina and out of the way, though very pretty. Castellina has at least 5 restaurants and a main street with shops. There are also a couple of take out places for pizza in town as well and the BEST gelato I've had! I think I had it twice a day! Within a very short drive are several vineyards that we liked as well and Greve, which is probably the best place to taste a number of wines is within about a 20 minute drive.
Radda had several restaurants and probably the same amount of shops. It is a lovely town, but off the path a little. Castellina is seriously right on the 222.
Greve might have more shops and restaurants than either place, but I felt Castellina was more charming. Just my opinion though.
We stayed in Castellina for 5 days in June of last year and 3 days in April of this year and I would go back again and again.

I think Radda and Castellina are comparable in terms of restaurants, shops, etc, although Castellina is slightly larger. Radda is also within about a 20 min. drive of Greve, and about 40 minutes from Siena. We did several daytrips from Radda to wineries in the area, as well as to San G.

Have you thought about staying near Greve? Vignamaggio might be worth looking at, although you have to be willing to drive back at night from restaurants, etc. Don't think they have nightly restaurant service available.

They are both more like villages with Castellina being the larger of the two. I think Castellina is more central if you were planning to do any day trips.

Vignamaggio is on the way to Greve off of the S222. They do indeed have dinner for guests some nights - you need to sign up for it in the morning or the day before. THere are several restaurants up the road from Vignamaggio on the way toward Lamole. They are good choices if you stay at Vignamaggio- a little out of the way otherwise.

Sky1,
We stayed in a villa that was on the grounds of the Fonterutoli vineyard last year. We were very close to Castellina. Radda is not too far away, nor is Greve. It was a great central location for Florence and Sienna. Although the other small towns were interesting, Castellina seemed larger and more charming. Over our two week stay, we ate at Fonterutoli’s wonderful small restaurant three times. The rest of the time, we "cooked in" with all the local produce and wonderful wines, so I can't comment on Castellina restaurants. Yes, the gelato was the best!! We made a gelato run almost every night….

You are only spending 3 days(2/3 nights). I would select Castellina as it is more central than Radda. You will certainly explore the area and that will make Radda, Greve, Gaiole and many more locations available for dining and exploration. Don't overlook the "white roads" in the area--they can vastly reduce transit time. BTW-you really can't go wrong, there is bound to be a lovely and enjoyable place to dine and each has its advantages as a home base. Cin Cin! Paul

Hi--both of these are lovely little towns. Neither has *ample* restaurants and shops. Have you looked at Greve? It may be more like what you are looking for, w/a town squuare that has quite a lively ambiance. We stayed in Panzano which is even smaller than either of the towns you mention, but is only a 15 or 20 min drive to Greve.

They all make good bases. Greve ,as social worker stated, is big enough to meet your criteria.

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