Volterra to Florence
On our first walk in Italy we decided to abandon the encumbrance of a weighty
backpack and use one of the many companies that offer self guided itineraries. We
chose the English company, Sherpa, which has a good reputation and whose
website was full of enticing routes in all parts of Italy. They were to provide us with
maps and walking notes and our baggage would be transported each day from one
comfortable hotel to the next. It was May 2000.
From the diversity of tempting options, we settled on Tuscany. The choice was
influenced by the lure of some of the most splendid art treasures in Italy, the classic
scenery of rolling hills covered in vineyards and a promise of fabulous food washed
down by Chianti Classico. We feared that the landscapes might prove to be a little
clichéd and that Tuscany's popularity as a holiday destination might spoil the
experience. We need not have worried: the countryside is beautiful and uncrowded.
A package of information arrived well before our departure and there was ample time
to pour over it. The maps were from an odd assortment of sources and of different
scales and seemed to be a bit dodgy. But there were very detailed instructions for
each day's walking and advice and warnings about some of the highlights or potential
difficulties we might encounter.
We took note of the fact that some of the tracks would be indistinct, signage was
plentiful but sometimes obscured by vegetation, there could be ferocious dogs and
some creek crossings might be tricky if there had been recent rain. We would need
to buy bus tickets before boarding buses and there were recommendations for
trattorias and cantinas. Most importantly we had a local contact called Ingo who
would come to our rescue in times of need.
The starting point for the walk was Volterra, easily reached by train and bus from
Pisa. Volterra is a sizeable town, predominately mediaeval in appearance but also
retaining many features from its earlier Etruscan and Roman pasts. It stands on a
hill, as do most towns in Tuscany. It is surrounded within mediaeval and Etruscan
walls pierced by a number of ancient gates.
Our hotel was just outside the imposing Porta San Francisco just a short walk to
the Piazza del Priori, the main square in the historic centre. The beautiful and very
formal square is enclosed by austere mediaeval mansions, one of which is
decorated with the emblems of Florentine magistrates. Other sights include a very
fine museum housing a collection of Etruscan archaeology discovered in the area
and a well preserved Roman theatre.
Although there was much to see in Volterra our first day was spent on a short
walking excursion to familiarise us with Italian ways and with the signage, maps
A bus conveniently took us to the small village of Pignano where there is a 12th
century church and an 18th century villa, both secured in private and exclusive
ownership. It was roughly 10km back to Volterra following gravel roads through
undulating country taking in splendid views of the surrounding area. Walking
towards Volterra there was a good view of the craggy landscape of ravines, known
as balze, caused by erosion and rock falls and into which buildings perched on the
edge have slipped.
Our first warning to watch out for dogs came to nothing and we returned safely to
enjoy dinner in a small osteria in the historic centre
Day 1. Volterra - San Giminiano - 14 km
Day 2. San Giminiano - Colle di Val d'Elsa - 13 km
Day 3. Colle di Val d'Elsa - Monteriggioni - 15km
Day 4. Monteriggioni - St Columba (Siena) - 11 km
Day 5. Siena
Day 6. Siena - Radda-in-Chianti -13km
Day 7. Radda-in-Chianti. Circuit from Radda to Vertine and
return to Rada -16km
Day 8. Radda-in-Chianti - Panzano in Chianti - 16km
Volterra to San Giminiano
We met Ingo this morning when he arrived early to pick up our bags
and to take us to a crossroads just beyond Pignano where the walk
began for real. We struck off along a "white" road lined with cypress
trees and found ourselves in a landscape of woods, vineyards and
sprawling farm buildings.
We investigated a ruined mediaeval village called Castelvecchio where there are the remains of
quite extensive hilltop fortifications. Some kind of settlement had been perched on this hilltop
since Etruscan times but now the remains of stone towers and old walls are virtually buried in
the woods. Apparently archaeological works are planned. A nearby village was picturesque on
From here there were way marks, alternatively marked TR18 and TR19 and occasionally
disappearing. We crossed one of the hazardous dry creek beds, traced a circuitous route
through some vineyards and passed several fattorias where wine was for sale. The views across
the hillsides were dotted with the huge cranes necessary for the reconstruction of old farm
buildings for the villa-hungry expats. We found a ruin and lunched in the shade of its trees,
imagining doing a renovation and living in this almost fantasy world.
After a while the towers of San Giminiano came into view and, after more meandering through
vineyards, we found our way into a huge car park full of tourist buses. Entering the town by an
old gate we were suddenly in a network of narrow streets seething with tourists. Our hotel was
located in Piazza della Cisterna, just near the Duomo, with splendid views overlooking the
patchwork landscape of the days walking. Around 7.00 pm, as if by magic, the crowds
disappeared, leaving the now deserted town to the lucky few staying there.
San Giminiano, familiarly known as San Gim, is one of the most visited towns in Tuscany,
perhaps in Italy, and justifiably so. Its imposing grey stone towers are seen from miles around.
There are now only 13 of the original 72 towers that were built in the Middle Ages by noble
families. For reasons of pride and prestige they were built as tall as possible within the
confines of the walled town. But there was a height limit, decreed by one of the town's rulers,
so that no tower could be higher than his own.
Walking through the countryside
we see rolling hillsides topped with
towers, fortified castles or fine
renaissance style house. There
are neat rows of vines climbing up
the hillsides, clumps of pencil
pines on a hilltop or in lines along
a winding road. Villages of pastel
coloured houses with terra cotta
roofs sit in the valleys or on the
tops of hills and the surrounding
fields are planted with olive trees,
wheat and sunflowers. And, of
course, the cranes.
The classic Tuscan landscape
Before you arrive in Tuscany you
know the Tuscan landscape. You
have seen see it in romantic films
and you have seen it in the
background of Renaissance
paintings - portraits, pastoral and
civic scenes and religious
paintings. The great paintings of
Piero della Francesca depict a
landscape very like the countryside
of his home town San Sepolcro
and the portraits of Boticelli and
Leonardo often have a backdrop of
gentle hillsides and cyress-like
San Giminiano to Colle di Val d'Elsa
We left the next morning through another
of the old gates and the first hour's
walking was the highlight of the day. The
route followed little white roads to the
north and east of San Gim from where
there were splendid views over the
vineyards towards the towers of the old
town. Much time was consumed admiring
the view and taking photos
The next hour was a confusion of vague
route instructions concerning a shrine that
had disappeared into the undergrowth, a
house with green shutters that had been
repainted, a derelict building that had been
restored and an indistinct track that lead to
a river which, in spite of dire warnings, was
We crossed the river into more confusion
featuring a ditch, a crop, a hidden concrete
well and a track bearing 185 degrees into a
forest. Finally, after passing through two
unexceptional villages we arrived at a grand
gateway leading onto the main street of Colle
di Val d'Elsa.
Somehow a 13km itinerary had taken all day so we were glad to find
Colle Alta very agreeable. Its castle and narrow streets of 16th
century mansions and mediaeval tower houses cling to a hillside
which drops down to the much more recently developed landscape of
Colle Bassa. A little further off is the distinctly industrial environment
of Poggibonsi. All roads seemed to lead to Poggibonsi and we hoped
we could avoid going there.
A restaurant in a charming garden in the old stone wall of the town
produced a wonderful dinner, looking down on a plain of twinkling
lights. Down below the traffic roared along the roads in the valley
Colle di Val d'Elsa - Monteriggioni
With the morning came the realisation that the first part of the day
would be a detour through farmland to the west and south of Colle.
This was necessary to avoid some of the unremarkable urban
environment but there was still an unavoidable couple of kilometres
through the streets of Colle Basse. After negotiating this we found
our way into rolling farmland, passing several pretty and well kept
hamlets on low hilltops. Some rare red and white waymarking led
us into a forest where a confusing network of pathways had us
doubting our sanity until we emerged again into vineyards and
came to the village of Abbadia a Isola. The interesting Romanesque
church here was part of an old abbey that once controlled a
strategic position on the Via Francigena or see also.
From this point we started to see views of Monteriggioni, an
incredible hilltop town enclosed within a low wall into which are
incorporated 14 sturdy square towers. The frustrations of the day
disappeared as we climbed up a very steep, cobbled roadway to
reach the imposing gate into this delightful mediaeval village.
Monteriggioni is completely contained within its walls which are still
virtually intact. There are very few streets but it is still possible to
lose yourself while wandering around admiring the stonework,
doorways and archways of the old buildings. There are records of this
village from the 12th century and a castle was constructed in the
early 13th century. Dante used it for his image of giants standing
around the rim of the pit of Hell. It is one of the best preserved walled
towns in all of Italy and well worth the accolades.
Our hotel room was a suite of rooms above a bar and overlooked the
main piazza whose focal point was a Romanesque church with the
simple plain facade typical of Italian churches from this period.
Having shown us around, the bar tender disappeared and left us to
our own resources. Dinner was in a smart restaurant nearby where
the other diners were a film crew doing some shots of the town.
Although it is inevitable that there are many visitors at the height of
the season, in May we saw very few others.
Monteriggioni - St Colomba (Siena)
In the morning it became clear that Monteriggioni is a very laid back outside of the busy times.
There was absolutely no sign of breakfast and neither our bar nor any of the shops in the village
were open. After cooling our heels for about half an hour in anticipation of the bar opening we gave
up and set off. Fortunately we had bought some things for lunch the night before.
It was a day of easy walking through the low Siena Hills, across farmland and through surprisingly
dense woods. We walked on white roads and forest tracks and the way marking was "mostly very
good", as our notes assured us. We were advised to keep following Route 102 and red and white
markings that would appear from time to time. Well the theory was good, reality a little different,
but we muddled through.
There was great confusion of marking (and lack of it) deep in the forest but we knew pretty well
where we were due to the presence of the savage barking dogs that were well documented in the
notes. Rundown farmhouses were concealed in the forests surrounded by sheds and kennels
where furious hunting dogs were kept.
Our objective was San Colomba where there was a post office/cafe and the bus stop for Siena.
After a very welcome cold drink we were sitting on a stone wall waiting for the bus when, to our
delight, Ingo arrived and transported us effortlessly to our hotel in the wonderful city of Siena.
Little needs to be said by us about Siena. If you have been there you
will have your memories, if you haven't you will have to read about its
treasures and plan to visit one day.
We spent the best part of two most agreeable days there: sitting in
cafes in the Piazza del Campo sipping a drink and people watching ,
laughing at the excessive scale and decoration of the Duomo,
looking at paintings and churches, exploring the narrow streets of
the historic centre and walking through the parks that overlook the
city. We particularly loved the two great paintings by Ambrogio
Lorenzetti in the Palazzo Publico - The Effects of Good and Bad
Government. They could be depicting the running of any big city of
To top it off our hotel room overlooked half the local football stadium.
Siena in black and white was playing. The players would disappear
from sight for minutes on end before streaming back with great
urgency. We watched with as much enthuasism as the Sienese
crowd as Siena thrashed the visiting team from somewhere.
Siena to Radda-in-Chianti
It could take the best part of a day to walk out of Siena so Ingo drove
us to the small village of San Sano where we were to start walking.
This is the great advantage of the organisation a company like
Sherpa can offer. No need to suss out bus timetables or organise a
taxi. He also undertook to get us tickets for the Uffizi in Florence so
we wouldn't have to waste time in a queue.
In San Sano we admired a
remarkable statue of a frog
indulging in a drop of chianti
and then set off to immerse
ourselves in the region of the
This was to be the best day of
the whole walk.
San Sano is a mediaeval village of villas and holiday accommodation
in the Chianti Hills. This is the heart of the celebrated Chianti
Classico wine and home to many expatriates from England,
America, Australia, Germany and who knows where else.
The route found its way through well tended vineyards and olive
groves, occasionally alongside stone walls and past many restored
villas. The hamlets of Ama, Cassanova, Galenda and San Giusta
were picturesque in a very Tuscan way. Way marking was pretty
good. We mostly walked along white roads but there were
occasional scrambles along indistinct tracks through scrub and
yellow broom bushes.
An unavoidable stint along the busy road brought us to the eastern
entrance gate of the old hilltop town of Radda-in-Chianti. We walked
along the narrow main street of the mediaeval town, delighting in the
beautiful old palaces that lined the streets. Through the western
gate of the town we came to the house where we were to spend the
next two nights.
Our accommodation was a
lovely room that opened
onto a terrace with a view
over vineyards and clusters
of farm houses surrounded
by cypress trees to the
Our hostess sig.ra Baldini
was most welcoming and
breakfasts, the highlight of
which was freshly made
We found the Bar Dante just
inside the town gate where
we dallied before dinner.
There was a choice of
restaurants where we ate
Radda is enclosed within its solid defensive walls and retains its
mediaeval appearance. In the 15th century it became headquarters
of the Chianti League, a military alliance established by Florence to
counter the territorial expansion policies of Siena. Its attractive
features include narrow streets, beautiful old palaces a central
piazza and a Romanesque church. Other churches in the
surrounding villages date from the same period and some have
beautifully restored frescoes.
This was a day that could be made as easy or hard/short or long as
we wished. We chose the easier/shorter option which was still a
good days walking through more of the lovely Chianti landscape.
Yesterday's steps had to be retraced for a bit then we headed east,
walking along a ridge towards Vertine, another walled village which
has remained almost intact since its medieval beginnings. It is
approached through an arched gate alongside a tall square tower
and there is found a cluster of little streets and closely assembled
stone buildings. We found an agreeable bar for lunch, listening to
conversations in German.
That evening Radda was celebrating a religious festival: our Italian
wasn't good enough in those days to grasp its significance. An
excited parade of beautifully dressed little children wound through
the streets, the church bells rang and rang and every house had a
procession of candles leading to their front door. We were enchanted
to find that sig.ra Baldini had set a line of candles to our doorway at
the side of her house. We were under divine protection.
Radda-in-Chianti to Panzano-in-Chianti
On this last day we left sig.ra Baldini's house and followed a
pathway through the landscape we had been looking at from our
terrace. We followed lines of cypress trees along white roads until
reaching the picturesque village of Volpaia where a well placed
cafe provided an opportunity for mid morning coffee.
Now there were olive trees alongside the path, apparently at 700
m, this is the upper limit for olive cultivation. Olives gave way to a
tangled woodland of oak, chestnut and heather and we continued,
first descending through the forest and then climbing onto a ridge
and to the summit of Monte Querciabella. It was a rather bleak,
scrubby environment up there, the ridge dotted with satellite
dishes and TV towers but the view was splendid. It was a good
place for a picnic lunch before beginning the descent on white
roads towards Panzano.
Panzano is attractive town on a hilltop and our hotel, called Villa
Sangiovese, had the right ring about it. Located on the attractive
small square of the village it was once a 15th century winery.
Nearby Greve-in-Chianti is another pleasing small town, often
considered to be the entry point into the Chianti wine growing
region. Its main piazza is an interesting triangular shape fronted by
attractive mediaeval buildings. The Saturday morning held in the
piazza is very popular.
Radda is only about 30 km from the city Florence. A short bus trip
dropped us conveniently at the station and it was then a short walk
to our hotel in the centre of the city. We marvel when people talk of
tackling the traffic in a city like Florence. Why would you do it?
Two wonderful days in Florence satisfied all the senses - fabulous
art and architecture, lovely parks to explore on foot and superb
food. This was a splendid finale to our walk which had been a
wonderful introduction to walking in Italy. Much more would follow.
Piazza dei Priori,
Wall plaques, Volterra
A villa in Tuscany?
Arriving at Colle di Val
Streetscape in Colle
Ancient church in Colle
Gateway out of
Village of Volpaia