I’ve been to the Chianti region several times (see The Towns of Chianti post). I hope this wasn’t my last trip to Chianti but if it was, it couldn’t have been more beautiful–crystal clear blue skies, warm sun, fall colors.
Getting There
To get there though, and pretty much to stay anywhere in Chianti, requires a car. And the drive from Montecatini Terme to San Leonino had me massively stressed. Here’s what I wrote:
5:00pm: Whew! Made it to Belevedere around 2:15pm–taking more than 2 hours to get here. The guy at Europcar kept pushing us to go on the autostrada. When I said ‘no’, he actually gave us some good advice– to go from town to town–Monsummano to Fucecchio to San Miniato to Certaldo which we did finally finding our way to Poggibonsi Nord and the Firenze Siena Autostrada (FiSi). I thought I’d taken us the wrong direction after exiting the FiSi but all was well and we got here OK. We never would have found our way otherwise ‘cause we didn’t see a road sign ‘til south of Castelfiorentino.
Where to Stay
Hotel Belvedere di San Leonino
https://www.hotelsanleonino.com/
We stayed at Hotel Belvedere di San Leonino, which has been our favorite hotel in this area since we first stayed there in 2010. While the grounds, location and the rooms were as beautiful as ever, there was not the warmth from the staff that we’ve enjoyed on past visits. I wrote an effusive review several years ago when my daughter, sister and I stayed there. On our last morning one of the staff walked up to us outside and pointed to the west saying, ‘Our gift to you.’ In the distance you could see San Gigmignano and that moment stayed with me for years. These days the staff is much colder and I attribute that to the fact that most of their guests come from a country not known for its warmth.
When we first stayed at Belvedere there were guests (including families) from all over the world, from Australia to Israel. And we loved watching and listening to the interaction. Now no one talks in the restaurant or bar. And the staff is equally uncommunicative. Still after the dark and depressing Hotel Reale in Montecatini Terme, it was a little slice of heaven as you can see in the gallery below. You can read more about Belvedere in my Where to Stay post.
Hotel Belvedere di San Leonino
Where to eat
Hotel Belvedere
We ate at the hotel restaurant two of the three nights we stayed there. After the first night I wrote: We had a pleasant dinner here–the usual pre-dinner prosecco, wine, pasta, grilled vegies and a huge dessert. No wonder I can’t lose weight. The wind seems to have died down but it’s still chilly. So guessing no outside dining tonight or tomorrow. 🙁 Last night after dinner I had another wine and Sue had an espresso in the bar. We had a few laughs which we needed after a stressful few days.
On our last night’s dinner at Belvedere we decided just to have salad and an antipasto tray, then we blew it by ordering a dessert. We’d intended to share one dessert but the waiter brought us each our own dessert. We would have corrected the error, but the staff was fairly cold and unfriendly. I think they intentionally made the error and we didn’t have the nerve to tell them. In the past the wait staff has been very pleasant and welcoming, even giving us free after dinner drinks but not this year. In fact this year the staff acted super annoyed when Sue and I got the giggles over a menu item that was translated as ‘soup with cereal.’
The food both evenings was good if not exceptional. The biggest disappointment was not being able to dine al fresco. I have several pictures of the outside dining in my Places to Eat post and it is beyond beautiful.
Osteria Fonterutoli
We ate here twice in 2014, once with my niece and her friends and once with my daughter. I remember the food as being exceptionally good but it may have been the company, talking and laughing our way through the food and wine. My sister and I had the eggplant timbale appetizer which is excellent, then she had a pasta and I had roast pork. With wine and water and a shared dessert dinner was almost 60 euros which is fairly steep for a small restaurant in the countryside.
Bar Dante
Our first morning in Chianti, we drove to Radda where we decided to stop for a cappuccino and brioche since we’d declined to pay for the über expensive breakfast at Belvedere. After circling the town, we decided on Bar Dante and here’s what I wrote: ‘We stopped in Radda and had phenomenal brioche and cappuccino….’ Phenomenal doesn’t even cover it. The brioche were freshly baked and melt in your mouth good. And the cappuccino was as delicious as any I’ve had in Italy including our favorite spot in Firenze, Caffé la Finisterrae. Plus like most smaller cafes the cappuccino and brioche were only 1.20 euro each. We enjoyed it so much we went back the next morning.
Bar Dante
I’m pretty sure this is the same café where we stopped in 2014; we being my sister, niece and two of her friends. We had enormous pizzas which helped with the hangovers we were still nursing after too much vino the night before.
Vineyards
I’ve written about these vineyards in my Vineyards, wineries and enotecas post, but wanted to write about them here also, in part because I think they’re all lovely and want as many readers to see them as possible.
Castello di Fonterutoli
https://www.mazzei.it/it/Tenute/Castello-di-Fonterutoli/La-tenuta/
My sister, niece, her friends and I did a tour of Fonterutoli in 2014 that we thought was great. Both my sister and my niece shipped home cases of wine. To do the full tour you need to make a reservation at their website https://www.mazzei.it/en/The-estates/Castello-di-Fonterutoli/The-estate/ . The tour plus a tasting costs 25 euros payable when you arrive.
I asked my sister if she’d like to do the tour again and she eagerly agreed. All I wrote in my journal after this year’s visit was that the tour and tasting were great, lasting almost two hours. I liked it even more than the first time, in part because our guide was so enthusiastic and provided detailed information on the winery which has been in the Mazzei family since the 15th century. We started outside the modern facility where the harvest was in full swing and grapes were being sorted. Then we went to the fermentation area where our guide explained the gravity system Fonterutoli uses for moving wine through the tanks, saving energy. In the lowest level where the barrels are stored and the wine begins the aging process, she described each type of barrel and how and why it’s used.
On our first tour our guide told us that the new facility was specifically designed to take advantage of the effect of the surrounding limestone and the water flowing through it to keep the cellar at the correct temperature for aging. However our guide this time said that this system was basically serendipitous; that initially the owners were unsure what do with all the water flowing past the walls, eventually designing a system for gathering the water and taking it to a pool outside the facility. It’s fascinating to look through the glass wall on one end of the cellar area and see the lime stone and flowing water.
Fonterutoli Vineyards
We finished with generous pours of four wines in their lovely tasting rooms. We didn’t order wine to ship though, since the price has gone up substantially from our last visit.
Castello di Brolio
ricasoli.com
I first read about the Castello in a guide book then looked it up on line. The garden tour with a tasting looked like a good way to try something new during our Chianti visit, having been to several other vineyards in the area. I was somewhat surprised to find that you have to hike close to a mile, first on a gravel road then on steep steps to get to the ticket office where you can buy a 5 euro ticket which includes the castle grounds plus a tasting. The grounds and the views from the ‘terrace’ of the castle are stunning, though, and worth the hike. There were also interesting sculptures by a Polish artist representing children lost in war.
Castello di Brolio
After walking back to the parking area we drove to where we thought the enoteca was located. Not finding it we went back to the parking area and walked to the osteria where a staff person was extremely rude acting like we should have known that the enoteca is on the main road through town. After finding the enoteca, which is small but very pretty, we were curtly informed that we could have one (small) taste of one wine out of 6 possibilities. Our wines were nice but no one asked if we were interested in buying, a mistake on the staff’s part given all the wine we’ve bought at tastings.
Il Molino di Grace and Santa Margherita
http://www.ilmolinodigrace.it/
https://www.santamargherita.com/en/
We didn’t visit these two wineries/vineyards while in Chianti but rather on a tour from Firenze during our last week in Italy. I booked through Viator finding out later that it’s just a ‘re-booker’ through TripAdvisor. I wrote an extremely negative review—-huge group in a large bus, late start, most of the time spent in the bus, wasted time in Greve, rushed tastings especially at Il Molino where we had to do our tiny tastings standing up. Plus our appetizers were bowls of cubed cheese and salami that everyone dipped their hands into.
That said Il Molino di Grace (The Windmill of Grace) has some of the most beautiful grounds I’ve ever seen. If I get back to Chianti, it will be at the top of my ‘to do’ list.
Il Molino di Grace
Santa Margherita is a much bigger winery and as we pulled up, it looked rather industrial. But they gave us a generous glass of prosecco first, then two tastings of red wines, that were slightly more generous than Il Molino. Plus we were able to take our second pour into their tasting room or terrace, both of which are lovely, and sit for a while.
Our ‘guide’, surprisingly from the U.S, touted their whites from the Veneto. So my sister bought a half bottle of pinot grigio which turned out to be the oddest pinot grigio I’ve ever had. I would go back, though, just to enjoy the terrace.
Santa Margherita
If you’re interested in reading about more vineyards, go to my Vineyards and Enotecas post.
Sights to See
The Towns
Our itinerary for the two full days we had in Chianti was set somewhat by the fact that I wanted to try out a couple of different options for getting to the E73 which goes to Perugia. As I was looking through a travel book, DK Eyewitness Backroads of Italy, which has 24 scenic driving routes throughout Italy, I noticed a drive that I thought might work. The route went from Siena along SS674 which becomes the E73, exiting at the 484 then north through Castelnuovo, past Castello di Brolio and Gaiole, and through Radda and Castellina on the 429. So we did the reverse, timing ourselves from Gaiole to the E73. The next day we drove part of the route from Castellina to Montevarchi, where you can pick up the A1 and take it to the exit for Perugia.
As we were returning to the hotel our first day along the SS222 we had to stop between Castellina and the turn to San Leonino while tractors placed hay bales along the road. When we got back to the hotel, we found a notice outside the office that this stretch of the 222 would be closed Saturday for a Formula One race.
While we were relieved that the race wasn’t on Friday when we were leaving for Perugia, we were sort of disappointed that we didn’t get to see the race. My sister took some pictures of the race preparation and I looked up information on the race which you can see at: http://www.coppachianticlassico.com/
I’ve written about all these towns except Castelnuovo in my Towns of Chianti post, so I’ll just add some galleries and a few comments.
Radda
My favorite thing to do in Radda is to stroll along the path that follows the overlook on the edge of town. The views are spectacular. I also love the little shops, especially those selling ceramics.
Radda in Chianti
Gaiole
Gaiole is generally much quieter than the other towns in the area and we just enjoy walking the main street and taking photos.
Gaiole
Castellina
Castellina typically has more tourists than Radda and Gaiole and this year was no exception. As is the case with most towns throughout Italy, parking is outside the centro. Occasionally I’ve parked in one of the lots on the outskirts but once in a while I’ve found parking on the streets near the centro. You need to be careful, though. One year I came back to my car and found it blocked in my small Italian cars and it took forever to get it out.
The shops and restaurants on main street through the centro were very busy but as always very pleasant. Here’s my entry: We parked outside Castellina, strolling to the centro, taking pictures and again Sue got some gorgeous ones. We stopped at a pizzeria and shared a pizza and I had the worst glass of white wine ever. We took more photos in the piazza then checked out an enoteca that advertised free shipping for a case of wine. Their white was excellent and their Chianti decent so Sue bought a case.
Castellina
Castelnuovo
I’d never heard of Castelnuovo and was surprised as we drove past it on the 484 to see what looked like lovely gardens along the road. So we stopped on our way back from the E73, parked on the edge of the centro and walked to the main piazza. We couldn’t find a way into the gardens so walked through the piazza taking pictures. We thought it was an exceptionally pretty but also exceptionally deserted town.
Castelnuovo
Places to Go
Badia Coltibuono
As I’ve written in my Vineyards, wineries and enotecas post, I saw Badia for the first time on a Backroads bike trip and took my sister, niece and daughter there in 2010 and 2014. While Bada has excellent wine, I’ve never purchased any on site. Typically we go for the beautiful grounds and views.
We didn’t stop in 2016 and so I was excited to see it again. We decided to stop on our second day after checking out the route to Montevarchi. Here’s my journal entry: I hadn’t seen the sign for Badia on the way out but realized as we drove back that it’s right at the T intersection for Montevarchi/Gaiole. We parked at the shop and walked to the monastery/albergo. It couldn’t have been more beautiful–intense blue skies, mile after mile of mountains and cypresses. I sat outside and soaked it up while Sue went in the church. And have to say her pictures are gorgeous (unlike mine.)
Badia a Coltibuono
Ceramiche Rampini
As I’ve written in my Museums, Monuments and Interesting Things to See Post, I visited Ceramiche Rampini the first time with a Backroads Bike tour and have been back twice since then. Here’s my journal entry from our 2018 visit: Then we drove to Ceramiche Rampini [from Badia] where there was a Backroads van and at least 20 bikers. I blurted out to one of them that I’d first seen Ceramiche on a Backroads trip 25 years ago. And she looked at me like I had two heads. It was almost all middle aged couples and I felt sorry for what looked to be the lone woman.
Still it’s a lovely location and we enjoy strolling the grounds.
Ceramiche Rampini
We finished our last afternoon in Chianti walking through the vineyards near the hotel and then having a white wine on the patio of Belvedere. While we were disappointed that we didn’t get to have dinner al fresco that night, the afternoon on the patio and walking through the vineyards couldn’t have been more perfect. As you can see in the gallery below, the weather was as spectacular during our stay in Chianti as it was not so great in Montecatini Terme, plus the beautiful weather continued through our first two days in Perugia.
Scenes of Chianti
Sempre Chianti!

OK, you ate and drank your way across
Italy. But you missed the Formula 1
race, which would have been great to
read about. Go back and do that next
time.