Cycling Southern Tuscany: Buonconvento - Pienza

  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
  • Photo of Cycling Southern Tuscany: Buonconvento - Pienza
Photo of Cycling Southern Tuscany: Buonconvento - Pienza
Photo by flickr user rayced


The landscape of southern Tuscany varies from steep valleys and volcanic slopes dotted with hot spring fuelled spa towns to dense forests and lush vineyards, olive groves and fig trees growing along the wide river banks. And the architecture varies from simple hamlets to Renaissance city icon, Pienza.

Seeing it by bike ensures you see as much as possible.

This seven day itinerary is a circuit from Bunconvento and back via Pienza. Many of the regions highlights can be see on day trips out of these two centres, which pleasantly means you don't have to carry your luggage with you every day, which is of definite benefit when it comes to not having to worry about it while you're admiring the great works of Tuscan art and architecture, and wandering though a museum or winery or two.

Day One: Arrive in Buonconvento

Buonconvento This pretty Tuscan commune is south of Florence and south east of Siena in the watercolour scenery of the crete senesi. Its small, but well stocked museum of traditional Tuscan art and the town's architecture and ancient enclosing walls are more than enough to keep you entertained on your first day, but if you're keen to get out on your bike the surrounding countryside is also pretty as a photo.

Day Two: BuonconventoMurlo – La Befa - Buonconvento

MurloMurlo is neighbour to Buonconvento so it has quite a bit to live up to if you're choosing to stay in one of the two. Murlo's best features are quite different to Buonconvento's though: it has the hill of Poggio Civitate – an ancient settlement being investigated for its archaeological value: some of the remains found here suggest that the ancient Tuscans had more in common with the Etruscans than the Italians of the time.

Plan to arrive early to see the excavations on your way through to La Befa, which is a hamlet with only about a dozen houses, all of them charming: old but restored with new stonework and brick. In spring the whole quiet place is grown over in flowers – which sprout even from between the huge stones of a Roman villa which is just out of the centre of the hamlet. If it's a perfect day your ride will be accompanied by very varied birdy voices, and you'll spot some, if not all of the following: badgers, hedgehogs, weasels and maybe even a snake by the side of the trail. The quickest route is along the railway, but there are more scenic routes along the Crevole River if you're not in a hurry – it's approximately 31kms worth of riding.

Day Three: BuonconventoMonte Amiata Montalcino

Mount Amiata Today's riding take you right into the heart of the Brunello wine region – all the cycling is on the pretty back roads lined with olive groves and vineyards. Cycle upwards towards Tuscany's highest point: Monte Amiata, which is actually a dome of lava – and one of several. Nothing volcanic has happened here for the last 300,000 years, though there's still some thermal activity going on in the little spa towns of Bagno Vignoni and Bagni San Filippo. These days as well as growing a lush cornucopia of produce, including olive groves, chestnut trees and grape vines, Monte Amiata's slopes are also skied down. They're also covered by several nature reserves, home to a more varied family of creatures than most people would expect from Tuscany – they have eagles and buzzards here!

The second point on today's route is Montalcino, worth stopping at for the fortress, the Pallazzo Comunale and the delicious red wine: Brunello di Montalcino. There's been a town on this mount since the 9th century – or at the very least a monastic commune – and it has many lovely old buildings, including the 14th Century fortress and cathedral and 13th Century walls, piazza and town hall. Beyond the appeal of the man made structures is the view – over Asso, the Arbia valleys and Ombrone: a view over olive groves, vineyards and orchards, as well as more pretty red stone hamlets.

One of the nice things about this itinerary is that you don't need to carry your luggage with you every day, and today's riding ends up back where you started in Buonconvento if you opt to travel the whole 39kms. If you want a shorter day stay overnight in Montalcino.

Day Four: Buonconvento - Monte Oliveto Maggiore - Sant’Anna in Camprena monastery - Pienza

Monte Oliveto MaggioreIt's uphill again to the Monte Oliveto Maggiore Benedictine Monastery, one of the largest in Tuscany, but it's the colour of it: sunset coloured bricks against the sandy coloured soil, that makes it so memorable as far as visitors are concerned. You have to cross a drawbridge and under a terracotta archway adorned with a sculpture of a Madonna with Child and Two Angels to get inside. The monastery's Great Cloister has vaults underneath it which house an impressive collection of frescoes depicting the life of St. Benedict, and within the main church are frescoes of Jesus Carrying the Cross, Jesus at the Column and St. Benedict Giving Rule to the Founders of Monte Oliveto, all by Sodoma – these are all very famous works.

Second stop on the day is another monastery, the Renaissance built Sant’Anna in Camprena Monastery, which was used as a location for the film 'The English Patient', and is loved for its frescoes. Pilgrims used to used rest here on their way to Rome and you can still arrange to stay here if you're needing a bit of the kind of TLC the beauty and traditional monastic cures afford.

Pienza If the monastic lifestyle is not for you ride another 16kms on to Pienza. In 1459, Pope Pius II took it upon himself, as powerful leaders do, to refashion his birthplace of Pienza into the perfect Renaissance town. His architectural visions were actually realized and the town is now a World Heritage site. The Duomo, with its slightly Germanic influence, the Palazzo Piccolomini, Palazzo Communale, and Palazzo Borgia are a few of the town’s gems, and the gardens at Piccolomini provide excellent picnic spots.

Day Five: Pienza - Bagno Vignoni Circuit

Bagno VignoniThough these cycling days aren't particularly strenuous, it's always nice to sink into hot water after a few days riding, and in the case of this itinerary it's a legitimate part of your journey: part of any visit to Bagno Vignoni. The Romans settled here to be near the thermal springs, and people have visited ever since for the same reason. The village's main baths are where you'd expect the piazza to be – which must be almost totally unique, and beautiful considering the charming architecture surrounding the pool. It's about 24kms return with options for some more adventurous riding in the morning before you languish in hot mud and water for the afternoon.

Day Six: PienzaMonticchiello - Montepulciano Circuit

Monticchiello Between Pienza and Monticechiello is a much photographed road that zigzags up and down a bright green hill between tall, narrow cypress trees. You don't have to ride via this road, but it's a much immortalised image of Tuscany and very photogenic – the kind of photo you might consider blowing up and putting on your wall back home. Monticchiello is in the valley, a medieval village retaining much of its ancient architecture: the old defensive walls, the castle and its tower, and many buildings within the village as well.

Beyond Monticchiello is Montepulciano of the red wine. Many Tuscan towns are beautiful, medieval treasures with narrow streets leading up to impressive fortress castles on hill tops. Many of them are also surrounded by lush, wine producing areas – but not all of them as as famously well endowed, either with beauty or wine quality as Montepulciano.

MontepulcianoOn the architecture and scenery side the main attractions are the main square – made in the great tradition of lovely Tuscan main squares, most specifically in the tradition of the Palazzo Vecchio in Florence - the Cathedral of Santa Maria Assunta and its art, the 16th century church of Santa Maria della Grazie and the Sanctuary of the Madonna di San Biagio.

On the wine side don't confuse the Vino Nobile Montepulciano with wines made just using the Montepulciano grape, which share the name though necessity – round here they don't take fondly to folks who don't appreciate the difference.

The round trip out of Pienza is about 33kms.

Day Seven: Pienza - San Quirico d’Orcia - Buonconvento

San Quirico d’OrciaThe final days ride takes you back to now familiar Buonconvento via San Quirico d’Orcia. Once on the Via Francigena, one of the main roads through Europe in the Middle Ages, San Quirico d’Orcia still has the same medieval street plan it did when it became part of Siena midway though the 13th Century. As well as stopping to admire the architecture and take note of the local churches, as you must do in every Tuscan town, the highlights of this one are the Horti Leonini gardens, the Misericordia and the Collegiata dei Santi Quirico e Giulitta.

After lunch it's an easy cycle back to home base, the whole days cycle is around 34kms.

For help planning your cycling trip through southern Tuscany contact one of WR's Cycling Travel Specialists.

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