The Towns of Chianti

Florence and Fiesole as well as Siena and San Gimignano are the topics of separate posts (see Florence and Fiesole, and Siena to St. Gimignano)  This article will be about the smaller towns of Chianti that I’ve come to love.

On my first bike trip to Italy (with Backroads) we started at the outskirts of Florence and rode on (or near) the Chianti Highway to Greve, staying over night there.  The next day we biked to a country inn about half way to Siena.   We stayed there a night or two, then rode on to Siena, where we stayed on the edge of town and did  loops to Castellina, Radda, and Gaiole plus spent a day exploring Siena.

We finished our trip with a stay in San Gimignano and a side trip to Volterra.

In the past 6 years I’ve returned to Greve, Castellina, Radda and Gaiole three times and San Gimignano twice.

When my sister asked me to take her to the places I visited on my bike trip, I included these four towns.  During that trip I wrote in my journal, “Today we had a leisurely breakfast then headed out to Castellina, Radda and Gaiole in Chianti.  Sue seemed to enjoy Castellina and Radda and the spectacular scenery which is much more mountainous and forested than southern Tuscany. But it started to rain in Gaiole and we had to sit in the car and eat our fruit.  We drove from there to Badia a Coltibuono, buying a few things in the shop and wandering through the 12th century Abbey.”

And that’s become our usual tour. (2018 update:  And in late September 2018 we visited all our favorite places in Chianti.  You can read about it in one of my recent posts, Sempre Chianti.)


As I mentioned above, my introduction to Greve was an overnight stay there on my first bike trip in Italy.  About all I remember is that we stayed in a rather funky hotel above the loggia on the main piazza.

Arriving in Greve

In 2010 my sister and I stopped in Greve on our way to Florence after staying in the Chianti countryside, arriving on a market day which was kind of crazy but fun and interesting.


Still it’s a lovely town and in October 2014 my sister and I, my niece and my niece’s two friends stopped here for lunch on the way from Florence to Hotel Belvedere.

We walked around town, taking lots of photos, then had a fun lunch in the town square laughing over a text one of our group sent to her husband with a picture of the bronze nude saying ‘thinking of you.’ His response was a bit off color but very funny.

In 2016 our walking group stopped in  Greve briefly after  lunch in a nearby vineyard (see Vineyards, wineries and enotecas post).  We just had time to take a couple of fun pictures. 



In terms of the beauty of the surrounding countryside and the beauty of the towns themselves, it’s difficult to choose between Castellina and Radda. After my first bike trip I probably would have chosen Radda, in part because I love the view from the walls on the edge of town.


But after the last two  trips to the Chianti area, I’m leaning towards Castellina. The main pedestrian street through the centro storico, is not only lined with lovely shops and nice restaurants but with charming and interesting sculptures.


When my sister and I were in the Chianti area in October 2014, we took her daughter and friends to Castellina (and all the other towns in this blog) the first week and my daughter the next.  During the first week, one of my niece’s friends bought a beautiful painting of the Tuscan countryside in one of the Castellina galleries.       I think she was very happy not only with the art but with the shipping and overall professionalism.  (As an aside in my opinion the owner (manager?) was incredibly patronizing.  I have an LLM in international law from Georgetown and when I made a comment about customs, he rudely cut me off.)  My niece fell in love with the ceramics in one of the shops but we could never seem to get there when it was open.

When my sister and I brought my daughter here, we spent most of our time sitting outside at one of the cafes on what was one of the last beautiful fall days.

Then we walked around the edge of town and took some pictures of the views and the town itself.

In 2016 my sister, niece and I had planned an afternoon of strolling and shopping in Castellina after lunch in a vineyard nearby.  Unfortunately it started raining just as we finished lunch and was pouring when we got to Castellina.  We still parked and went into the centro, running in and out of stores picking up wine, fruit, cheese and bread which we took back to the hotel for a dinner on our terrace.  Dinner was great but we were very bummed not to be able to do our usual strolling, shopping and sipping.


As I mentioned above,  when I came to this area on my first bike trip, Radda made a bigger impression on me than the other towns.  Like most of our trip it had been a rainy day and most of us chose to ride in the van until we reached Gaiole (see discussion below).

After our lunch in Gaiole we all manned up and rode our bikes to Radda stopping first at Ceramiche Rampini (see Museums, monuments and interesting sights  post.)

I thought it was  delightful despite the clouds and rain.  We took lots of photos around town and especially from the overlook on the edge of town which provides gorgeous vistas of the Chianti countryside.

Me outside Radda
bike van in Radda

So I made sure to bring my sister here in 2010 and  she loved the views as well as the charm of the town itself.

In 2014  my sister and I, my niece and her friends came here after we had been to Badia a Coltibuono (see Vineyards, wineries and enotecas  post).  As I mentioned in my  Where to stay  post, we had had way too much to drink the night before and  needed the walk around the grounds of Badia to  get rid of our hangovers.

When we came back through Radda, food was beginning to sound good again so we stopped at a little pizzeria fronting the road through the town.  The owner told us, or so we thought, that one pizza would feed two so we ordered two for the five of us.  As you can see below, one would have fed us all  but they were delicious.

We followed our lunch with a walk around town and a visit to the overlook on the edge of town taking pictures of the beautiful scenery.

My sister, niece and I made a brief visit in September 2016.  We had reservations for lunch at a vineyard west of Castellina and decided to visit Radda first.  At that point it was a beautiful day and we enjoyed checking out the shops and the usual photo ops.











My introduction to Gaiole was on that first bike trip when we also rode to Radda and Castellina.  Most of us rode in the van to Gaiole, since it was another rainy day.  Even riding in the van, we were all damp and chilled when we got to our destination for lunch.  Our guide said it was a restored castle owned by a Scottish couple.  It was both a restaurant and hotel and perhaps because of the weather, the lunch was memorable.  We had tortellini soup and tiramisu, my first experience with both and they were delicious.  We were all holding out our bowls asking for more like a scene out of Oliver Twist.  One of the first things I did when I got home, was to figure out how to make the soup.  (Tiramisu was another story.  It wasn’t until I took a cooking class in the fall of 2016 that I learned how to make a great version of this dessert.)

I’ve looked all over the web for that ‘castle’ but nothing seems to fit with my memory.  If any reader knows this place, please leave a comment.

I brought my sister here in 2010 during our brief Tour d’ Chianti but weirdly enough it was raining so we just walked quickly through town then ate our lunch in the car.

During our 2014 trip, we stopped here and walked through town.  My niece’s friends thought it was lovely and took quite a few pictures.

 It’s difficult to choose my favorite area of Tuscany but I love driving through the wooded hills of Chianti and stopping at small towns and vineyards.  (See Vineyards and Enotecas.)  On our trip in September 2016 we had planned to try a new vineyard (Azienda Agricola) just west of Greve in the town of  Montefioralle which is supposed to be one of the most beautiful hill towns in Tuscany.  But it was raining and we were worried about getting back to Firenze on time–at least I was, so we canceled.

As I’ve said in my other blogs on favorite cities and towns, every time I come to Italy, I always want to see a few of my favorites and then something new.  This coming fall of 2017 I’ll be heading to Firenze, then northeast Italy so I won’t get to see much of Tuscany.  But there’s always another trip.  You can read more in my  Sempre Chianti  post.












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