Overview
We had a most interesting and challenging experience with this walk in probably one of the most scenic and interesting areas of Tuscany—Chianti!
This is what we expected from the tour guide brochure:
- We would discover the fine wines and rustic dishes of Tuscany’s Chianti region as we explored the trails and medieval walled towns between Florence and Siena.
- We would tour Florence at the start, Europe’s most celebrated city of art. We would stroll across the Ponte Vecchio bridge and visit the Uffizi gallery, where the Renaissance masterpieces of Carravagio, Botticelli and Da Vinci hang.
- We would journey south into a perfectly formed landscape of rolling hills cloaked in olive groves and neatly terraced vineyards.
- We would follow forested trails and farmers’ tracks into a succession of historic hilltop towns.
- We would meander through the piazza in Radda in Chianti and the idyllic setting of Gaiole in Chianti.
- We would visit Siena’s Piazza del Campo, the perfect opportunity to round off the walk with a local Chianti.
Did it live up to our expectaions?
- We discovered some great wines and local pastas and lasagnes of the Chianti region as we hiked the trails and medieval walled towns between Greve and Gaiole. We had lasagne overload plus many more and some excellent wines-even though we preferred local beers in the very hot conditions.
- We toured Florence at the start, Europe’s art gallery. We strolled across the Ponte Vecchio bridge, visited a number of galleries, and had a good couple of days in the city. An excellent self-guided tour did the trick.
- We journeyed south from Florence through the beautiful landscape of rolling hills cloaked in olive groves and neatly terraced vineyards.
- The hiking on the trails was a challenge following forested trails and farmers’ tracks into historic hilltop towns. The maps supplied to us were very poorly described, inaccurate, confusing and misleading. Trails were probably neglected during COVID 19. Maps had trails marked in red, without and information regarding the location of landmarks or buildings. This we intend taking up with the tour company. The local tourist information centres in the villages regarded the maps provided to us as being totally inadequate and misleading. As a result we got lost on occasion—not due to our poor map reading skills. The company had an app which we could use—but there was no internet connection in many areas along the trails. Google maps was unavailable.
- We thoroughly enjoyed the piazzas in Greve, Radda and Gaiole.
- We had a brief visit to Sienna and then took the train back to Venice.
Day-by-day
Greve to Montefioralle
We started our walk in Greve in Chianti from the piazza. Leaving the town on foot, climbing to the hilltop hamlet of Montefioralle. The arrow shows the road we came up on—it was steep and a good climb, though it was only a few kilometres away from Greve. The heat was a challenge.
We started at the bottom passing vineyards and the most beautiful medieval town awaited us at the top
Montefioralle was most inviting
We walked through the cavern of streets, looking for Amerigo Vespucci’s house. An Italian lady who could speak no English made herself clear by gesticulatory measures where the house was.
Montefioralle village onwards
We set off through the most delightful countryside following our walk through Montefioralle.
Cresci arrived in Italy from Germany in the 3rd century A.D. and was shortly after that, befriended by Minias. For practising the emerging and as yet unrecognized Christian cult—and refusing to acknowledge the Roman gods—the two were arrested, with Minias put in the Florence arena to face the lions.
According to legend, the lions left the devout Minias unharmed, and thus, to satisfy the Roman audience, Minias was beheaded before the viewing public. Cresci, on the other hand, was placed in prison, where he encountered a guard named Ognone, whose sick child Cresci healed. Ognone converted, freed Cresci, and the two, along with another prisoner named Emptius, escaped to the rural country outside Florence, specifically to a place known as Valcava, in the Mugello.
Wikipedia
Greve Hotel and Wine Festival
When we got back to Greve— we didn’t hold back. The band played on as we enjoyed a lovely pasta and the local wine.
Volpaia
After a taxi ride to Badia a Montemuro, we embarked on a scenic trail to the fortified village of Volpaia, where we had plans to savour the world-famous Volpaia red wine. With a winemaking tradition dating back to the late 12th century, this charming town beckoned us to embrace its rich heritage.
We went down a vehicle track past a vineyard where we savoured a bunch of grapes. This track ran next to a water and gas pipeline, which we followed. The path was overgrown with blackberry branches and thorns. As we extricated ourselves from the thorns, we were attacked by myriads of horseflies, which ceased their attacks while we were walking at a decent pace.
We entered boggy terrain with little creeks crossing everywhere. We kept our eyes peeled for yellow pipeline marker poles.
We crossed the Fosso Balatro Creek—broad and shallow. The path became muddy with many puddles and clinging mud. We had to find a place to sit to take off our socks and shoes. Aging bodies did not take lightly to sitting on jagged rocks.
We had to take off our shoes and socks here and wade over the mud and sharp rocks in the dam over the track. The tracks served as mountain bike trails, too! We were busy taking off the socks and shoes when we heard them! They drove past us—waving and exchanging greetings.
We climbed a very steep hill, Monte Porcinati after we had passed another elderly couple also following the trail. They gestured to us that we should go up the mountainside. Up and up we went—sheer mountaineering! A deer ran out of the undergrowth and over the top. I shouted to Dedrie, but she was trundling up the hill behind me, looking for the turn-off. I blurted out breathlessly that I had just seen a ‘ginormous’ deer. There was no turn-off to be seen. The turn-off had become invisible due to the dense undergrowth.
We eventually reached an intersecting track at the top. We searched for markers for the gas and water pipelines. Those markers had disappeared. The intersecting track beckoned left or right. We had to guess. Dedrie had seen the mountain bike trail markers. This would prove to be a ‘lifesaver’ She was adamant, ‘We should just walk along the mountain bike trail, and that should get us to our destination.’
Then, the same mountain bikers appeared on their Sunday afternoon ride. We were glad that we had been nice to them when they showered us with mud and water earlier while we were drying our socks and shoes.
In a mixture of one Italian word and many frantic English words, I gesticulated, ‘Piacere—we are on the wrong track! The bikers communed together, nodding their heads and pointing in various directions. ‘You go’, they pointed down the track we were on. Then they made some gestures that we interpreted as ‘Veer left, then right, then left, then right and so on and so on for a long way—then you will get there’.
We watched them disappear into the thick bush. Silence settled on the track. It was getting later and later that Sunday afternoon. Thoughts of spending the night haunted us both!
We tried the phone and Google Maps. There was no reception! But, we persevered along the bike tracks, knowing that they must take us to some larger track or road. We kept on the bike track, up and down, left and right. For about a km there were no landmarks—the bike tracks had taken us down into the valley. We craned our necks and listened intently to see if there was any sign of habitation—a medieval castle or the hum of a motor car.
We came to a broader track. And then, we heard it—a car came up the track. We ran, but they were too quick for us—gone before we got to them. But, we did not give up hope as we knew the car must have come off some larger road and the bike tracks we were walking along were well-frequented. Also, we still hoped that we would soon cross the track we were supposed to be on.
After seeing the car drive past, we walked for another half and hour or so, with hope rising when we saw a village on the hilltop.
Then, Dedrie shouted, ‘Someone’s coming’. A tall khaki-clad figure emerged from the bush. It was a Dutch hiker and his partner. Geez, were we glad to see them! They were in bad shape. The first thing the Dutch guy said to me was, ‘This has been too hot a day. I can hardly carry on further.’
They were heading down the track from which we had just emerged. ‘Do you know where this leads to?’ I asked. ‘Yes, I think we know where we’re going—we’ve also got an App that tells us where to go’. ‘Poor bastards’, I thought. ‘Hope you can get reception and hope you’re gonna be OK’. Then I said, ‘Do you know where this track leads to!’ They replied together, ‘You guys are fine—this track leads to a main road, about a couple of km away. From there, you can walk straight into Radda.’
And so we did. We hoped that the directions would be better the following day.
Beyond Volpaia, the trail unfolded along picturesque ‘white roads’ embraced by cypress trees, guiding us to the hilltop church of Santa Maria Novella, a testament to enduring Romanesque beauty.
Surrounded by vineyards and olive groves, the Pieve di Santa Maria Novella is one of the oldest Romanesque parish churches in the territory of Chianti.
A few kilometers from Radda in Chianti, on the road leading to the delightful village of Volpaia, it is also known as Pieve di Chianti and, although it was remodeled several times during the 19th century, it still retains the original perimetral base dating back to the Middle Ages.
The bell tower itself, on the left side of the parish church, is a 19th-century remodel, but retains its Romanesque-era base.
Inside the parish church is a gilded copper Processional Cross – dating from the 12th century – and two terracottas from the workshop of Santi Buglioni: the Madonna and Child with Saints Peter, Lawrence, Stephen and Paul, and the hexagonal baptismal font.
A really interesting detail are the three columns supporting the arches of the three naves: the capitals – a unique case in Chianti – are decorated with lions, eagles, angels, floral motifs and gospel symbols. Similar decorations dating back to the same period, in fact, are found only in Valdarno and Casentino.
Tuscany official tourism website ©2024
After Pieve di Santa Maria NovellaWe continued along a very scenic, rather busy road through lush vineyards, up a very steep mountain into the enchanting hilltop town of Radda in Chianti, one of the region’s most revered wine towns, ready to reinvigorate our numbed senses.
We did manage to take some pictures.
The Road to Gaioli
The next day, we left Radda on the way to Gaiole.
We walked to Gaiole through wooded valleys, vineyards and olive groves. We rambled through the picture-postcard Tuscan landscapes. Our track ran alongside a beautiful stonewall and delightful vineyards.
We were super vigilant—following the guide meticulously and methodically. This time, we had to bypass a creek, which dammed the track. We took a path to circumnavigate the dam—landing in a ‘grassy field’ as described in the guide.
Then our directions were to follow a ‘narrow path’ that widened into a gravel road. Cheerfully we walked on and on until we reached a stone wall—as per the guide. We were told to turn left when the track ended at a driveway. Only snag was that the gate was heavy and locked. We could not get past it. The guide did not indicate how to get around it! We decided to follow a stone wall.
We continued along the stone wall—we were supposed to find a ‘semi-hidden vehicle track through an archway between a garage and a house!’ We searched high and low for this landmark. We then realised we were walking in ‘unchartered territory’. We knew that we were not lost as we heard a motor vehicle drive past on a road above us.
But before reaching that road, we had to walk through six inches of clingy mud that extracted a blob of clay as we extracted our shoes.
Our spirits buoyed, we reached a good gravel road that led to a tiny hamlet. We set off there to ask for directions. We went into the hamlet, landing up in the backyard of someone who was working on a laptop outside. We knocked on the door, and out came a stocky, smiling Sardinian who could speak reasonable English. We asked him for directions to Gaiola. He had to ask another Italian man close by for directions. They talked for a long time, gesticulating and pulling faces as they spoke. Dedrie and I tried to fathom what they were talking about. Eventually, the Sardinian spoke—pointing back in the direction we had come.
‘See that road’, he said, ‘Follow that to the asphalt and then walk to Adine and all the way to Gaiola. We sat on a stone wall in the shade, had our fruit brunch and finished a bottle of water before we continued down to Adine.
We reached Adine. We walked along the asphalt under very big trees that provided very much-needed shade. There were farmers and workers busy in the vineyards. The rolling hills in the distance reminded us of the lovely Victorian countryside—the dense bush alongside the road could have been somewhere in Central Africa.
There, in Adine, we sat next to a fountain—an important landmark! We rested on an old stone wall that encircled the old church of San Bastiano. We then started our journey down into the valley, descending for at least a km on the rockiest and most hazardous path we had ever traversed.
After resting at a small power station, we crossed an asphalt road over cattle grids into the vineyards of San Piero.
. A gentle but straightforward ramble took us into Gaiole.
We spent a good day in Gaiole after entering via the San Piero vineyards.
The Road to Lecchi
On our final walk day, we walked past the Church of San Sigismondo. We decided to take the main road to Sienna and then take the turnoff to Lecchi—rather than following the inaccurate and misleading map and guide.
We descended into the rich Tuscan countryside via the asphalt road, past the Castello di San Donato in Perano, a cluster of well-preserved 10th-century houses. On the left and right, we could see the woodland trails and densely wooded creeks and rivers. We kept a look-out for cars from behind—fortunately drivers were used to hikers along the side of the road and the road was not that busy!
The castle was built during the 10th century near the pre-existing chapel of San Donato, on a hilly area where pre-existing settlements from the Etruscan and Roman eras were located .
The architectural complex became a strategic military structure with defensive functions in the border area between the Florentine territory to which it belonged and that of Siena, and was then transformed into a fortified farm during the second half of the sixteenth century following the definitive fall of the Republic of Siena and its definitive annexation to the Grand Duchy of Tuscany .
Purchased by the Strozzi family during the second half of the sixteenth century following the decommissioning of the military structure, the complex was transformed into an agricultural farm and remained in the possession of the Florentine family until 1967 , the year in which it passed into the ownership of an agricultural company.
WIKIPEDIA
The information centre had given us an easier way to get to Lecchi. We would walk all the way along the asphalt until we saw Rozze Di Lecchi.
The information staff told us that many of the trails had been neglected since COVID-19. This explained why we had to fight our way through blackberry thorns wherever we went. I asked about the horseflies. She smiled knowingly.
But we found the turn-off. The road that led to Moci and then Lecchi was great!
Once we had our coffee, we headed to Lecchi, glad that we would be picked up there and transported to Sienna.
Sienna
We were picked up in Lecchi and taken to our hotel in Sienna. We spent a delightful afternoon visiting the Medici Fortress, close to our hotel and then had an excellent lasagne, beer, and the most delicious ice cream.
The fortress has an interesting history—there must be a reason for building walls that thick!
Construction of the fortress followed the Battle of Marciano which in 1554 marked the final defeat of Siena by its long-standing rival, Florence. It was located on the site of a previous fort, known as the Cittadella/Citadel, which had been built in 1548 on the orders of the Emperor Charles V after the city came under the control of Spain, subjected to the authority of the Spanish ambassador, Diego Hurtado de Mendoza.
On 26 July 1552 the Sienese rose up against the Spanish, expelling them from the city and destroying the Citadel/Cittadella.[2]
Slightly less than three years later, on 21 April 1555, after more than a year under siege by Spanish and Tuscan troops, the city surrendered. The Republic of Siena, supported by its French allies, continued to defy the Spanish from Montalcino, but the city of Siena itself was now back under Spanish control. Four years later, in April 1559, the Peace of Cateau-Cambrésis was signed between France and Spain. This left the Republic of Siena without allies and led to total surrender. The city fell under the control of Spain’s regional ally, the Florentine Duke Cosimo.
In order to prevent any attempt by the Sienese to recover their independence, Cosimo ordered the construction of the present fortress on the site of the earlier Spanish Citadel. The project was entrusted to Cosimo’s celebrated Urbino born architect, Baldassarre Lanci who had started his career as a military engineer. Construction commenced in 1561 and was completed just two years later in 1563.
The fortress was demilitarized only at the end of the eighteenth century, at which point it became part of the city’s public life. In 1937, following a major restoration, the fortress was transformed into its present condition as a public park. It houses an Enoteca (a commercial center focused on the local wine industry) and frequently hosts art exhibitions. It is also used for festivals and concerts and is home to the Siena Jazz foundation.
WIKIPEDIA
A monstrosity of a fortress—they were scared of the Florentines!