| Riding notes | Sights, food, wine, accommodation hints
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Day 1
Florence to Castellina-in-Chianti
via Greve-in-Chianti
55 kms
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From the city, cross the Arno river on the bridge Ponte alla Carraia and ride along via dei Serraglithe until the end of it; pass through the Porta Romana and
get into the roundabout. Take the centre uphill road, the via del Poggio Imperiale. At the end of it there is a big building, turn right and follow the signs for an
undulating ride to Impruneta (275 m). From the Piazza Buondelmonti, with the basilica in front of you, follow the road downhill until you come to a T-intersection with the
S222 (the Chiantigiana).Turn right along the Chiantigiana to Strada-in-Chianti and after that, there is a severe uphill to Le Bolle (247 m).
Continue on the main road until you reach Greve-in-Chianti (26 kms, 236 m). From Greve it is mostly uphill to Panzano (507 m), downhill to the turnoff to
Radda-in-Chianti to the left (don't take this) and then a very long and arduous uphill to Castellina (578 m) via Pietrafitta.
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In Florence, we enjoyed the historic cafes in the Piazza della Repubblica: Gran Caffè Giubbe Rosse & Caffè Paszkowski.
At Greve-in-Chianti, look out for the renown butcher, Antica Macelleria Norcineria Falorni at Piazza Matteotti 69 (sample the salami & superb prosciutto).
Castellina-in-Chianti has a medieval square plan and 15th & 16th Century houses dominated by the crenellated tower & castle keep.
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Day 2
Castellina-in-Chianti to San Gimignano
37 kms
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We took an early morning detour downhill to Fonterutoli which was pleasant. It means though you have to ride back uphill again to Castellina to start
your main
journey to San Gimignano.
From Castellina, this is a glorious rolling downhill ride (relatively free from traffic when we did it) for 21 kms along the S429 to Poggibonsi, a town worth avoiding.
This is generally easy to do as it is well signposted to San Gimignano - thank goodness, as the traffic here was incredible! After the city and a long mostly "flat"
stretch it is a very hard uphill to San Gimignano and at the roundabout at the top you may have to push your bike the last half a km to the old walled city. |
San Gimignano is worth the long climb: it is a real gem. The main throroughfare is very colourful, lined as it is with many shops selling the ceramics typical of
the region. Must-sees are the Town Hall (Palazzo del Popolo) and the Piazza del Duomo with its 52m high tower ("Torre Grossa") the highest tower in the town and from which
there are wonderful views. It houses the civic museum with many works of art such as Filippo Lippi's "Annunciazione" (1482), Marcovaldo's "Crucifix" (1260), the Tabernacle
of Santa Fina (the patron saint of San Gimignano) and Pinturicchio's "Madonna in Gloria" (1512); also of interest are the frescoes in the Sala di Dante (council chamber),
particularly Lippo Memmi's "Maestà" (1317).
We had a lovely chat with the woman at the Enoteca Bruni on via Quercecchio and purchased a bottle of Vernaccia di San Gimignano which is an excellent white wine
(this travelled many kms in one of our paniers until we had a chance to enjoy it later). And we enjoyed a glass or two at DiVinorum in Piazza della Cisterna out on
the terrace with its stunning valley views.
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Day 3
San Gimignano to Volterra via Certaldo
60 kms
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We detoured via Certaldo and although this added kms, it was well worth it as this is a really charming hilltop town and it is a lovely
undulating ride from
San Gimignano. Be warned though, the old town of Certaldo (up on the hill and called "Certaldo Alto") is accessed via a 15% climb unless you take the funicular
(I'm not sure if you can take bikes on this).From Certaldo, we had a hilly ride to Gambassi Terme (20 kms) where we had a very pleasant picnic lunch in the main square
next to a pretty park with views out over the Val d'Elsa. A steep climb out of town and then some gentler climbing before a long descent was just a warm-up for one of the
toughest climbs of our trip to Volterra (531 m) perched high up on the escarpment (this was 32 kms from Gambassi Terme, the last 9 kms of which was uphill).
We had to stop many times for breaks as it was very hot; the traffic at times was constant (there were lots of buses that had to grind slowly behind us as the
driver looked for a gap to overtake). We arrived relatively late in the afternoon which didn't leave a lot of time for sight-seeing but fortunately some of the sights
remained open plus we walked around early the next morning before breakfast and again before we departed for Siena.
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As mentioned before, Certaldo was a real find: a very pretty, quiet and small hilltop town dating from the 13th Century.
Volterra: We enjoyed an early morning walk around the outside of the 4th Century BC Etruscan walls. These mark the perimeter of the
"Parco Archeologico Enrico Fiumi", a lovely garden occupying the highest spot in town. The Piazza Martiri della Libertà afforded lovely views over the Cecina Valley and
in the late afternoon sun this was a nice place just to sit (along with the locals) and indulge in some people-watching. The Palazzo dei Priori has a fresco of the
"Crucifixion" by Piero Francesco Fiorentino on the staircase and a small antechamber on the 1st floor gives a bird’s eye view of the Piazza dei Priori below.
The front façade of the Cathedral in Piazza San Giovanni was designed in the 13th Century by Nicola Pisano and the vast interior contains several impressive works,
including Benozzo Gozzoli's fresco of the "Procession of the Magi" (1479) and there is local artist Zaccaria Zacchi's painted terracotta nativity scene, Mino da Fiesole's
marble ciborium (1471), the exquisitely carved 12th Century marble pulpit, and an exquisite 15th Century tabernacle by Mino da Fiesole.
Food: We enjoyed the most wonderful wood-fired pizza in the whole of Italy at Pizzeria da Nanni, via delle Prigioni.
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Day 4
Volterra to Siena
via Monteriggioni
53 kms
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Nice downhill out of Volterra (well, of course, since we'd climbed up the day before ... this was clearly going to be the daily pattern from here on in!!)
but then a very steady climb to Colle di Val d'Elsa (30 kms) along S68. Although a main road, the traffic wasn't a problem. From here to Siena it was quite pleasant
undulating riding although the turnoff to Monteriggioni is tricky to find. And finding your way in and out of Siena is a nightmare without a good city map. |
Colle Val d’Elsa: 10-13th Century town with the lower Colle Bassa comprising many shops selling glass & crystal. I would liked to have spent more time here,
but then again, arriving at lunchtime will find many things closed. I found out later it had a very good art museum: the Museum of Civic and Religious Art.
Monteriggioni: Built in 1203, the intact fortifications make the town the most significant example of a “walled land” in Sienese territory. Apparently, it made
a big impression on Dante who referred to it in one of his cantos. For some reason this place didn't do much for me. Maybe it was a bit touristy but then again, these
things depend a lot on your mood at the time.
Siena: I was underwhelmed, but then again I'm not mad on big towns. Nevertheless, it was lovely when the evening light played out over the city.
Similarly, an early morning walk the next day was quite delightful. Highlights include the famous fan-shaped Piazza del Campo; the Duomo with its splendid façade & art
gallery is one of the most spectacular Gothic churches in Italy (1136-1382) and the inlaid marble floor is superb; finally, the Basilica of San Domenico had a lovely
ambience when we visited it on an early morning walk.
Food: We had a wonderful meal at the Osteria Castelvecchio (via di Castelvecchio 65). And the Drogheria Manganelli, at via di Citta 71 -
which has been a Sienese institution since 1879 - had the most divine ricciarelli (Siena’s soft almond cookies); I wished I'd bought more!
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Day 5
Siena to Montalcino
via the Abbey of Monte Oliveto Maggiore
50-60 kms
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This was a really tough day: one of our toughest. The hills were very steep and we had to push our bikes up a couple of them. The scenery out of Siena was wonderful -
once we found the correct way out! This was a nightmare and a good city map is a must. There were new freeway works on the outskirts leading to Taverne d'Albia and we
must have travelled back and forth about 3 or 4 times trying to find a way to the S438 until we finally took a section of the new freeway, honked by fast-travelling
vehicles as we went. Not very pleasant. But the countryside beyond this was lovely although hilly. We had a lunch-break at Asciano which is a really pretty town and
worth the stop. From here it is uphill along the S451 riding up and down from 200m to 330m with some quite steep gradients (15-16%). This got us to the Abbey of Monte
Oliveto Maggiore about 3 p.m. which was excellent timing as it is closed 12 - 3.
It was a nice ride downhill (at last!) - still on the S451 - to Buonconvento which seems to be a really nice town worth a longer visit but we knew we faced a severe
uphill to Montalcino (567 m) and, as it was already about 5 p.m., we kept going. It was hard-going but very pleasant in the late afternoon sun. We were pleased to arrive,
albeit very late in the afternoon.
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Asciano: As said before, this is a pretty town.
The Abbey of Monte Oliveto Maggiore: An absolute must-see. The frescoes depicting the life of St Benedict (started by Luca Signorelli in 1497 and completed in 1508 by
Sodoma) are wonderful, as is the Chapel of the Sacrament. Watch the closing hours: 12-3.
Buonconvento: Again, a delightful town enclosed within 14th Century walls (one of the few DOWNhill towns!).
Montalcino is famous for its excellent wine, the Brunello (considered to be the finest red wine in Italy). There is a very pleasant enoteca at the
fortress where there are breathtaking views of the entire Orcia Valley. And we enjoyed a simple but delicious meal at Fiaschetteria Italiana, Piazza del Popolo 6.
It would have been nice to stay longer in Montalcino. We stayed at a lovely B&B but the bloody church clock chimed all night - not just on the hour, but every quarter hour!!!
We had a lovely breakfast at the hotel - wonderful view! - and I think this would be a better place to stay (further away from the church!) but it was already booked out
when I enquired some months earlier. |
Day 6
Montalcino to Montepulciano
56 kms
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It was a lovely downhill ride to Mont'Antimo (14 kms) and then some ups and downs to Monte Amiata followed by a long but not steep uphill to Castiglione d’Orcia (540 m)
along the S323. Downhill then to Bagno Vignoni (15 kms from Sant'Antimo) which is off the main road a couple of kms uphill to the left just after the bridge over the
river at the bottom.Ride 5 kms along the quite busy S2 to San Quirico d’Orcia and take the turnoff to the right onto the S146 (before the overpass) for a long ride uphill
to Pienza (9 kms, 481 m) and then a further 14 kms to Montepulciano (607 m). |
Sant'Antimo: There is a beautiful 12th Century Romanesque church here where monks sing Gregorian chants lasting 12 minutes. Very special!
Castiglione d’Orcia: The centre of town with its stone-paved streets is meant to be picturesque. We stopped on the outskirts of town to walk up to
La Rocca which is quite interesting but should have stopped in the old town for lunch and a look a round. One of those regrets - we just cycled on downhill ...
Bagno Vignoni is a tiny medieval spa village with thermal pools. We were a bit stuffed and should have made the effort to look around a bit more and have a swim.
Pienza: The Church of San Francesco is one of the most ancient Franciscan buildings in Italy, dating back to the 13th Century. From the loggia of the
Palazzo Piccolomini are spectacular panoramic views over the Val d’Orcia below. Pienza had a market in progress when we arrived and was very busy with tourists.
Probably worth a longer stay but we were under pressure of time and had to push on to Montepulciano.
Montepulciano: We arrived late - about 6 p.m. - which didn't leave us a lot of time to look around but fortunately, with the long daylight hours at this time of
the year and then by making an effort early next morning, we did manage to take in some of the sights. We had the most superb accommodation with wonderful views overlooking
the Val di Chiana and out to Lake Trasimeno and I can highly recommend Hotel Il Marcozocco. The local wine Vino Nobile is wonderful.
Montepulciano would make a
good "rest day" on which a circuit back to Pienza via Montecchiello would have been great. The next morning we rode out via the lovely travertine church of
Madonna di San Biagio perched on a platform below the city walls.
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Day 7
Montepulciano to Piancastagnaio
50 kms
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Well if Day 5 was a tough day, this was THE toughest. We had planned to ride from Montepulciano to Sovana, a total of 78 kms, but there was NO WAY! The hills on this
day were relentless and by about 5 p.m. we pulled up at Quaranta just out of Piancastagnaio.I have tried to work out an alternative route but it seems to me, whichever
way you go, you are faced with huge climbs. We should have originally planned to take 2 days to reach Sovana. We should have made Piancastagnaio the Day 7 stop (it is
quite a pretty little town), and the next day ride down to Acquapadente for 25 kms (at 11 kms joining the S2 which wasn't at all busy when we rode it), turn off to the
right to Onano for Sorano (20.5 kms); it is then a further 10 kms to Sovana.
For directions to Piancastagnaio, we left Montepulciano and rode through the busy but charming town of Chianciano Terme (10 kms), La Foce (555 m), down then up to
Contignano (a pretty town, 481 m), 10 kms of undulating gravel road to Le Conie (598 m) and onto Abbadia San Salvatore (31 kms, 822 m - we actually climbed higher than
this before descending into the Abbadia, a nice ride: maybe because we were descending??). A further 4.3 kms brought us into Piancastagnaio (772 m) via ups and downs.
Had the plan been to stop here, it would have taken a lot of pressure off the day and it would not have been so arduous. |
Abbadia San Salvatore is one of the oldest monasteries in Tuscany (dated 743).
Piancastagnaio is an ancient town with a mighty fortress, Aldobrandesca. There are wonderful views over the surrounding countryside. |
Day 8
Piancastagnaio to Orvieto
60.5 kms
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This was a really nice day's riding. We had stayed overnight at Quaranta 3.5 kms outside of Piancastagnaio. From here it was downhill until we joined the S2 at 11 kms
for an undulating ride into Acquapadente (25 kms from Piancastagnaio) and a further 8 kms to San Lorenzo Nuovo from where there were lovely views to Lake Bolsena.
There was little traffic. We elected not to ride along the lake as planned as it was hot and not very scenic in the harsh light. Instead we took the S74 to Castel Giorgio,
then the S71 to Orvieto (24 kms): hilly but eminently rideable and the views over to the city of Orvieto sitting majestically on its tufa hill are brilliant. |
Orvieto has 2 Renaissance masterpieces: the glorious Cathedral of Santa Maria (1285) - considered to be one of the finest churches in Europe! It has the
famous fresco cycle by Signorelli of "The Last Judgement". And the 2nd must-see is the Pozzo di San Patrizio (St. Patrick’s Well): 60 m deep, 13 m wide and built by
Pope Clement VII. It comprises a double-helix staircase up which water was carried by teams of mules and more than 70 windows provide light & ventilation.
Food & Wine: We had avoided gelati until now so we could savour it at Gelateria Giuseppe Pasqualetti, Piazza Duomo 14: some regard this as among
the BEST gelateria in Italy. Pasticerria Montanucci at the top of Corso Cavour had yummy pastries and panini as well as excellent coffee. And the wine,
Orvieto Classic is recommended.
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Day 9
Orvieto to Todi
38 kms
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Mostly nice riding apart from the awful traffic in "lower" Orvieto (Orvieto Scala) and a steep climb at the end into Todi. Apart from that, it was pleasant riding
via Lake Corbara. We elected to take the main road as we didn't want to run into any problems with hills and we'd figured by now the main roads had less intense gradients,
if more traffic. As traffic had generally not been a problem it was seen as the lesser of the 2 evils. In fact the S448 was reasonably problem-free once we'd negotiated
our way out of Orvieto Scala; and this route looked less of a problem than the alternative S79bis which had one town at an altitude of 637 m. But it was certainly a
steep climb from the Rivere Tevere to Todi. |
Todi: There are many wonderful sights here: the town hall (Palazzo del Popolo) is reputed to be one of Italy’s oldest buildings; the Piazza del Popolo is described
as one of the most perfect medieval piazzas; the lovely Duomo has a magnificent rose window; and the enormous hilltop Church of San Fortunato is meant not to be missed as
it is a rare example in Italy of a Gothic hall church with frescoes by Masolino da Panicale & the tomb of San Jacopone, Todi’s beloved patron saint - however, it was
closed when we were there. We hiked the very pleasant Serpentine Walk to the church of Santa Maria della Consolazione on the outskirts of town - it is one of the
masterpieces of the Umbrian Renaissance.
Food & Wine: The traditional grain soup “farro” at Pane e Vino, via Ciuffelli 33 was great. And we enjoyed the gelati and some drinks at the
very pleasant Bar Painegiani, Corso Cavour 40 while we watched the world go by.
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Day 10
Todi to Assisi
58 kms
Day 11 - Rest Day at Assisi
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This was good riding, although the steep climb down and out of Todi was very testing to start. However, after Duesanti I found my cycling legs again and we had a
delightful ride through pretty vineyards to Montefalco (30 kms) via Bastardo (19 kms) along undulating roads.
Bevagna was next - a downhill ride of 6 kms; then 10 kms across flat fields to Spello; and finally a lovely late afternoon ride to Assisi: 12 kms,
the last few kms being uphill. |
Well, this was a BIG day with lots to see:
Montefalco, aka the “Balcony of Umbria” because of its superb views, is famous also for its DOCG Montefalco Sagrantino. A highlight is the Museo
Civico/Communale attached to the former church of San Francesco (closed 1-2 p.m.) which has a fine fresco cycle by Benozzo Gozzoli on the "Life of St Francis".
Bevagna: This is a beautiful 1st Century village with one of the most authentic Romanesque town squares in Italy, Piazza Silvestri (around which stand some
of Umbria’s finest churches). Off Piazza Garibaldi is the 13th Century Church of San Francesco which contains stone said to have been mounted by St Francis
when he preached to the birds nearby.
Spello is an enchanting and very beautiful little town. You can enter the walled town via Porta Consolare which is a well-preserved Roman gateway.
Alternatively, there is Porta Venere, a Roman gateway flanked by 2 imposing 12-sided towers dating from the Middle Ages. A must-see is Cappella Baglioni inside the church
of Santa Maria Maggiore, home to Pinturicchio’s most glorious fresco sequence of Jesus’ birth; also the floor of the chapel is made from majolica tiles from Deruta.
Assisi: Assisi is a great place. We had wonderful 2 nights accommodation at St Anthony’s Guesthouse, via Galeazzo Alessi 10 and can highly recommend it:
"as cheap as chips", small but clean and with a view over the whole of Assisi. We got in late but with just enough time to sit on the balcony with a bottle of red and
and watch the sunset! It was glorious.
The highlights are the famous Giotto frescoes of the "Life of St Francis" in the Basilica of St Francis and the crypt below where the remains of Italy's patron saint are
kept. Other highlights are the Basilica di Santa Chiara and the Duomo of San Rufino with its fresco of the "Crucifixion" by Doni and façade festooned with grotesque figures
and fantastic animals. From Piazza San Rufino we walked up to the Rocca Maggiore for great views of the Valle del Tescio, the Valle Umbra and Assisi itself.
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Day 12
Assisi to Gubbio
44 kms
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We left Assisi on the reasonably pleasant S147 to Ospedalicchio and then through to Piccione (10.5 kms). From here it was certainly tough riding along the S298
to Belvedere (7 kms of very steep climbing) and then a reasonably pleasant downhill to Gubbio (18 kms), although the road was busy (especially the last part into Gubbio). |
Gubbio: When you first arrive, you come into Piazza Quaranta Martiri, dedicated to 40 locals executed by the Germans in 1944; from here there are good views
upwards of the town. Nearby is Gubbio’s finest church, San Francesco and not far away is a Roman amphitheatre. Gubbio has a rich history of producing some of Italy's
finest pottery. In the Piazza Grande is the superb Palazzo dei Consoli which houses brilliant art works as well as an exhibition dedicated to the history of the famous
Eugubine Tablets (7 bronze slabs 300-100 BC). The Funivia Colle Eletto up the steep slopes of Mt Inginoto to the Basilica di Sant’Ubaldo affords great views
(there is also a path).
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Day 13
Gubbio to Umbertide
27 kms
Train to Passignano sul Trasimeno
Then cycle Passignano sul Trasimeno to Castel Rigone (11 kms)
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There was a better exit from Gubbio which we missed and we ended up on a freeway for a short time. We then had a hair-raising ride through Semonte with the cement
trucks (sic) but once the traffic cleared it was quite pleasant along the S219 to Umbertide. We then "cheated" (or maybe we were just getting smarter?) and took the
train through Perugia to Passignano sul Trasimeno which was a good decision as it 1) rained enroute and 2) we had looked at the map and seen the most awful ascents.
Instead, we arrived in Passignano sul Trasimeno as the sun came out and had a pleasant ride along the lake foreshore before riding the 11 kms to our agriturisimo
accommodation at Trecine near Castel Rigone: a few kms along the lake foreshore and then a very steep uphill.
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Umbertide: Its main feature is the square and circular towers of La Rocca. The countryside is scattered with fortifications due to the region’s strategic
military importance. Coming from Gubbio, look out for Castello di Civitella Ranieri (15th Century) one of the most complete and best preserved examples of military
architecture in the area; nearby but higher up is the splendid Castello di Serra Partucci.
Passignano sul Trasimeno is a town of Etruscan origin built on a chalk promontory. We enjoyed a really nice pizza and wine at a cafe looking out over the lake
while a rainstorm washed over. |
Day 14
Castel Rigone to Cortona
31 kms
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A buzzy downhill ride from Castel Rigone avoiding the huge cracks in the road: splendid views over the lake! It was pleasant riding along the lake foreshore on
S75bis and then we turned off near Tuoro for the uphill climb through Riccio to Cortona. |
Cortona: This was certainly the land of “Under the Tuscan Sun”. It is a really pretty place with lots to do. There is a 1 km walk along via Cruce, a long lane
with gardens either side leading to the 19th Century church of Santa Margherita and then onto the Medici Fortress with its stunning views. We returned via a warren of
steep cobbled lanes to Piazza Garibaldi where there are sensational views across the Val di Chiana to Lago di Trasimeno. Adjacent is a lovely public park. We had a
wonderful dinner at Pane e Vino, Piazza Signorelli 27 - which is very popular.
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Day 15
Cortona to Castelli di Gargonza
41.5 kms
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This was very nice riding firstly downhill out of Cortona; then once we got through busy Camucia we rode through the pretty Val di Chiana and its vineyards and
fields of sunflowers. It was 19 kms to Foiano della Chiana where we enjoyed watching the townsfolk emerge from church and we perused the nearby market that was in full
swing. We had a lovely quiet ride to Pozzo della Chiana (6 kms) for a picnic lunch by the road and then nice riding to Monte San Savino (8.5 kms) [Andrew saw a live
snake on the road here which he found very exciting]. From here it was a steady ride for 8 kms up to the enchanting Castelli di Gargonza.
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The Castelli di Gargonza is a 14th Century hamlet set in a magical pine and cypress forest. It would have been divine to have had a 2nd night here:
pure indulgence.
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Day 16
Castelli di Gargonza to Monte San Savino
8 kms
Train to Castelnuova di Garfagnana via Arezzo & Lucca
Day 17 - Rest Day at Castelnuova di Garfagnana
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We left early (sadly) for the downhill descent to Monte San Savino to catch the train to Arezzo. Arezzo is a lovely city and it would have been great to have spent
a night here. We had a quick look around and then took the train to Lucca. From Lucca, after spending the afternoon there, we took the train to Castelnuova di Garfagnana
where we stayed 2 nights. |
Arezzo is where Roberto Begnini's "Life Is Beautiful" was filmed. A must-see is Chiesa di San Domenico for the haunting "Crucifixion", one of Cimabue’s
earliest works (1265) above the main altar.
Lucca was the birthplace of Puccini. Along with the locals we circumnavigated the outer wall by bike shaded by the many plane and chestnut trees.
The Duomo (in Piazza San Martino) has a magnificent "Last Supper" by Tintoretto.
Castelnuova di Garfagnana: This is a picturesque town and the ride along the River Serchio to Ponte della Maddalena just north of Borgo a Mozzano was
a real joy.
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CYCLING IN ITALY
