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After spending a day revelling in the extraordinary sights of the Tuscan town of Siena, we drove out into the Tuscan hills towards the Chianti wine region. I must admit I didn’t really know much about this region, apart from what I’d seen in a movie called “Under The Tuscan Sun”. I knew the region was famous for growing grapes and olives, but had no idea that it was brimming with medieval Tuscan villages you must see.
We were booked into a hotel in a hilltop medieval village called Castellini in Chianti, and upon arrival we were completely blown away. The Hotel Palazzo Squarcialupi (don’t ask me to pronounce it!), on the main street of Castellina in Chianti, was a vision of 15th century Renainssance architecture overlooking beautiful gardens and vineyards in the valley below.
We discovered that we had been upgraded to a suite, featuring a separate living area and spacious bedroom in a loft above. Our own private little balcony overlooked the Tuscan countryside, worthy of an exclusive resort. We were in heaven!
Not only this, but it also had its own Day Spa – La Tinaia Wellness Centre, located in the basement of the hotel, with sauna, steam room, jacuzzi and changerooms equipped with everything you need. It was the ideal place to relax after a long day of driving and poking around the numerous medieval Tuscan villages we visited.
This charming Tuscan village, dating back to the fifth century B.C., located between Florence and Siena, was fortified by hexagonal walls that still stand today. Castellini in Chianti, whose emblem is the black rooster, main street of Via Ferruccio is dotted with little cafes, restaurants, wine cellars and souvenir shops.
As we strolled down the main street we noticed a few of the significant historical buildings, including our hotel – formerly the Palazzo Ugalini, Palazzo Bianciardi, The Church of the S.S. Salvatore, Piazza del Comune and the Medieval Castle.
For a fascinating look into Castellini’s history you can visit The Archeological Museum of the Chianti Senese that is located in the main piazza.
Each time we walked around the village during our four day stay, we noticed something new. On the main thoroughfare, via Chiantigiana, we came across the statue of the Black Rooster and a shop selling cycling jerseys from the Chianti Classico bike ride. We also came across a Winery, where you could partake in wine tasting and select from a vast array of local wines. We immediately thought, “why not”?
Possibly one of the highlights of our stay was an evening wine tasting and dinner tour to two local vineyards. We jumped aboard our mini bus with our guide and driver and wound our way around the narrow dirt roads of Chianti seeking out two particular wineries.
On arrival we were shown around the vineyards, that had been owned by the same family for centuries and afterwards got to taste their wines.
The family then served us a delicious traditional 4 course meal with wines to match each course. Along with cheese, olives and prosciutto, we were treated to the local dish of pappa al pomodoro, a Tuscan vegetable bread soup.
On our first day of touring Tuscany, after consulting the local Tourist Information Office, we set off into the Chianti countryside with a map and a recommended itinerary for our day’s driving. A short distance away, rambling through the undulating countryside, we came to Radda.
We had a stroll around the town and into the small park where there was a fruit and vegetable stall setup doing a roaring trade. We purchased a couple of sweet peaches to eat for our morning tea.
We came to the municipal building or Palazzo del Podestà, which was extended several times over the past couple of centuries to include jail cells.
Our drive continued to the small pretty hamlet, or castle of Vertine, that is surrounded by vineyards and olive groves. Vertine is located near Gaiole in Chianti.
The very well preserved Vertine with its original medieval appearnace is enclosed within massive walls. Inside the walls sits the quaint Church of San Bartolomeo a Vertine featuring renaissance frescoes on the interior.
What I liked about this 11th century castle is that it is still inhabited with residents that actually live inside the castle. There are no shops or other tourist attractions except one cafè serving coffee and fresh cakes.
We moved onto the small fortified village, referred to as a “castello” in Italian – Castello di Volpaia, which entailed a drive up an unsealed narrow road, not far from Radda in Chianti.
Volpaia retains a great deal of its original architecture and has been attractively restored. Although more tourist-driven, we found this village to be charming.
There are three excellent restaurants in this village with amazing panoramic views over the surrounding vineyards and forests, so it was the ideal place to stop for a bite of lunch and a glass of pinot grigio.
The winery that produces the wine Chianti Classico operates within the walls and you are able purchase the wine at the cellar door.
We wound our way up to another fortified village, just a few kilometres from Greve in Chianti, called Montefioralle. It’s probably one of the most ancient in Chianti and is still today enclosed within its original walls. Apparently during the Middle Ages it was one of the largest military and administrative centres of the area.
The ancient passageways, formerly the entrances to the castle, and the fact that is is virtually free of traffic, makes it an ideal village to explore by foot.
Vineyards stretch away in every direction round about the village that makes it perfectly picturesque.
The principal historic monument in Montefioralle is the Church of San Stefano, which is at roughly the highest point in the village.
We also noticed that there was a small cottage offering Italian cooking classes, just outside the village walls, which was very tempting if time had permitted.
On the following day we headed off in the other direction, on the western side of Chianti, towards the village of Barberino Val d’Elsa. The town has a long spindle-like shape, where the main road runs down the centre connecting the two main gates of the old town: Sienese and Florentine Gates.
Entering the Sienese Gate we encountered century’s old buildings with beautiful wooden doors and clean stone walls. Halfway down the street, is the Palazzo Pretorio and then further along the rear of the San Bartholomew church, and the Pilgram’s Hospital.
Walking around to the main thoroughfare, we came to the front of San Bartholomew Church and admired the terrace in front of this neo-gothic style church. We found it to be a beautiful spot to admire the soft hills and the patchwork of olive groves, vineyards and small forest alcoves, surrounding the town.
We were on a mission this day to visit the medieval town we had heard so much about. San Gimignano, a small walled village perched high on a hill about halfway between Florence and Siena, did not disappoint.
Although the most touristy and busiest of the Tuscan medieval villages, we were fascinated by its medieval architecture and towers that rise above all the other buildings.
The hill has been inhabited since the Etruscan and Hellenistic period, probably due to is dominant position that allowed a careful watch of the rich Elsa Valley below. The striking fourteen towers of San Gimignano of various heights, which have withstood wars and time continue to define the city making its unique skyline its international symbol.
A stroll through the core of San Gimignano, in the shadows of its surviving towers, is simply delightful. At the centre of the town is Piazza della Cisterna, named for the cistern that is served by the old well standing in the middle of this square. However, we found this square to be inundated with day trippers and quickly moved to the outskirts of the village and traced around the ancient town walls.
Nearby on Piazza del Duomo stands the town’s Romanesque cathedral. Also called the Collegiata di San Gimignano, the interior is the big drawcard. Inside the cathedral is extensively frescoed, dating back to the 1300s. The colours you see are the original ones painted and their vividness and brightness is awe-inspiring.
I must confess that the shops along the narrow streets, just after you enter through the main gate into the walled town are stupendous. My husband and I both purchased handmade leather bags, belts and shoes from a local shop. There was also beautiful linen items, such as tea towels, bread baskets, tablecloths, placemats and napkins.
After we walked and shopped, we were hungry and ready for some sustenance. Strangely enough we found this amazing cafe/bakery with Italian sweet treats that you would need to see to believe!
Apart from grape growing, the area is well-known for producing some of the best saffron in Italy; you’ll find the spice for sale in shops and as a flavouring in meals at some of the finer restaurants.
After we spent a good part of the day hanging around San Gimignano, we consulted the map the young lass at the Travel Information Centre marked for us, and set off for the castle of Monteriggioni, near Poggibonsi. As with all of the Tuscan castles we had visited thus far, this one was perched high on a hilltop overlooking vineyards and olive groves in the province of Siena.
We discovered that this particular castle represents one of the most important walled castles in the territory. Monteriggioni is incredibly well-preserved with an intact structure as if time had stood still. Its strategic position on a hilltop spectacularly dominates the surrounding landscape.
The castle was built by the Sienese between 1213 and 1219 for defensive purposes to be on the lookout for any armies approaching Siena. It impressively boasts 14 towers along which the guards used to walk and patrol the walls. There are also two gates, one called the Franca or Romea Gate and the other known as the Florentine Gate.
A few steps inside the gate and you’re already in the heart of the village in the main Piazza di Roma onto which the Church of Santa Maria Assunta faces.
The rest of the square is lined with shops, cafes and restaurants. Monteriggioni really has a strong medieval feel about it, as evidenced in mannequins dressed up as knights and shops that sell medieval artefacts.
Every July within the fortified walls of the town a special event is celebrated: the Medieval Festival of Monteriggioni, one of the best medieval festivals in the region.
Our four days in Tuscany flew by very quickly and we were understandably reluctant to leave this beautiful region, as we felt there was so much more to discover here. Each Tuscan village we visited was unique and had its own vibe. We could have easily lost ourselves here for a few more days under the Tuscan sun in a wine drunk haze!
Linking up with Travel Photo Thursday
Kathy was a 50 something year old when she started up this blog 6 years ago, but has since turned over another decade and is now in her early 60s. She is married with two adult children and lives on the Tweed Coast of New South Wales, Australia. Kathy enjoys living life to the fullest and loves to keep fit and active by maintaining a healthy diet and exercising regularly. Some of her interests include reading, photography, travelling, cooking and blogging! Kathy works part-time as a freelance writer but her real passion is travelling and photographing brilliant destinations both within Australia and overseas and writing about it.
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JoSeptember 20, 2017
Gosh what a wonderful time you had – your photos are fabulous and you’ve made me want to book a trip to Tuscany right away. Not possible of course, but I’ll be coming back to your post for ideas when we do :)
KathySeptember 21, 2017
We absolutely adored our time in Tuscany exploring the charming countryside and medieval villages. I could easily see myself returning here to see more of what it has to offer. :)
Lyndall @ SeizeThe Day ProjectSeptember 20, 2017
As you know Kathy, I do love a Tuscan village! Your post is chock full of them. There’s a few I’ve yet to explore, so will be popping them on the wishlist for our next Italy adventure. Love all your pics – takes me back there…. sigh! :)
KathySeptember 21, 2017
I’m pretty sure that I could be convinced to return to Tuscany. It was such an enchanting part of Italy. The countryside was breathtaking. :)
jodie filogomoSeptember 21, 2017
The stonework is amazing in these old towns!!
You have the most amazing photos, and what an incredible experience!!
KathySeptember 21, 2017
Yes these Tuscan villages are absolutely amazing. Each one a little different from the other. Thank you it was a marvellous experience. :)
EstherSeptember 29, 2017
Oh my, how gorgeous!! Husband and I have just returned from Bologna (which was amazing!) and I can’t wait to get back to Italy.
KathySeptember 30, 2017
There were so many gorgeous medieval villages in Tuscany that time did not permit seeing them all. I could have easily spent another week here. I’ve heard very good things about Bologna too. Italy is incredible and I would love to go back too. :)
RuthOctober 1, 2017
In Tuscany, I have only been to Florence and Pisa. However, I know the uniqueness of the region is on the country side. You visited a lot of different towns (I haven’t heard about half of this). I need to follow your itinerary one day. #TPThursday
KathyOctober 1, 2017
Tuscany was one of the many highlights of our trip to Italy. Our 4 days here barely touched the surface of the wonderful medieval villages that abound in the region. You could probably spend weeks here!
BeeOctober 2, 2017
wow, i had no idea there was such cool medieval architecture to discover in Tuscany. I admit, I also associated it only with wine farms, but never bothered to do more research. It looks like an amazing trip, and I love your photos.
KathyOctober 2, 2017
Yes there is more to Tuscany than just it being a wine region. It has some very pretty countryside and many historic medieval villages. We had an incredible four days here.
Faith CoatesOctober 2, 2017
My dream bucket list trip and your photos and information do not disappoint. We first learned of this araa of Tuscany years ago when our young neighbours honeymooned there and their photos were just amazing. Reading your descriptions and looking at those beautiful locations just pull me to visit. I cannot wait to take my time and explore the area in full. I want to spend a month or more just wandering the region and trying all the wines oh and the food….
KathyOctober 3, 2017
You could spend months here exploring the Tuscan countryside, visiting the wineries and tasting the delicious food. We barely touched the surface of what this region has to offer. It’s a beautiful region of Italy.
RosieOctober 3, 2017
Wow your pictures are beautiful! It all looks so picture perfect, I didn’t realise there was so much medieval architecture in Tuscany. The wine and food tour sounds great too! We love joining food tours during our trips.
KathyOctober 3, 2017
The pictures barely do it justice. The entire region is so pretty and it is full of medieval villages with interesting histories. There are wineries and olive groves everywhere you look on the horizon. Beautiful region.
AdaOctober 3, 2017
What an amazing view! I have never been in Tuscany before but its my dream! Your photos just wanna make me wanna book a flight,pack my suitcase and visit all those stunning villages ! It looks so beautiful there! Amazing green landscape, small climatic streets and amazing wine! What a dream!
KathyOctober 3, 2017
Yes it is a very scenic region. We loved our time rolling around the Tuscan hillside visiting villages and wineries. It was so relaxing.
RachelleOctober 4, 2017
Tuscany is really something out of a dream. The history of the region, the beautiful landscape, and the stunning architecture make it a treat for the eyes and brain, figuratively speaking. Wouldn’t it just be a dream to take cooking classes all around the region? Ahh.
KathyOctober 4, 2017
Oh yes I would love to do the cooking classes, then eat the delicious food – washed down with some of the local wines! Tuscany was so much more beautiful than I ever imagined.
VictoriaOctober 4, 2017
Wow! What amazing photos. Thanks for including so many of them. Hopefully I can go to Italy soon with my husband.
KathyOctober 4, 2017
Thank you Victoria. Photography is one of my hobbies, so I like to take plenty of great images to accompany my travel blogs. Italy was like a dream come true for me and I would highly recommend it as a travel destination.
KellynOctober 8, 2017
Tuscany has been on my bucket list for as long as I can remember. Since H.S. actually. What is it with these little villages and the beautiful streets with shops and cafes. They make me want to never return home.
KathyOctober 8, 2017
Tuscany is a beautiful region in Italy that has retained it’s charm and doesn’t have the crowds that other parts of the country has. I could easily lose myself here for months.
Sandy N VyjayOctober 9, 2017
The small towns of the Tuscan region are real gems. They look as if they have emerged from the pages of a fairy tales book.We have not been able to explore the interiors of the Tuscan region much, except probably Fiesole which is actually very near Florence. Hope to explore and discover these beautiful gems next time around.
KathyOctober 10, 2017
These beautiful gems are very worthy of spending a few days road tripping through Tuscany. I hope you get to see them on your next trip to Italy.
ChieraOctober 11, 2017
One of my favourite things about Europe is that there is history EVERYWHERE. I have never been to Tuscany, and really don’t know much about it, but it looks absolutely stunning. That view from your room is to die for!
KathyOctober 11, 2017
We did stay in the nicest hotel with those magical views looking out over the grapevines and rolling hills. Tuscany is a must see for history buffs – there’s medieval villages everywhere.
David JonesOctober 16, 2017
Topic is interesting too.
I really Liked it.
Thanks for sharing this one with us.
KathyOctober 17, 2017
Thank you. Tuscany is a superb region in Italy. I could return here again and again.