Cycling in Tuscany

  • Photo of Cycling in Tuscany
  • Photo of Cycling in Tuscany
  • Photo of Cycling in Tuscany
  • Photo of Cycling in Tuscany
  • Photo of Cycling in Tuscany
  • Photo of Cycling in Tuscany
  • Photo of Cycling in Tuscany
  • Photo of Cycling in Tuscany
Photo of Cycling in Tuscany
Photo by flickr user lo.tangelini

Eating and drinking well and appreciating great art and architecture is what a lot of people come to Tuscany for.  But taking it all in on two wheels adds something to your explorations of medieval hilltop towns and fields of grapes and other fresh produce – and it's not just that spending all day pedalling means you can fully sate yourself in the evening without feeling guilty - it's also that this more leisurely way of getting around means you can't help slowing down a bit and letting the Tuscan attitude towards quality of life take over. And that's just delicious.

There are numerous potential cycling routes running though Tuscany, from day trips round flat valley regions, to jaunts amongst the vineyards and hilltop towns, to artistic pilgrimages, to more strenuous rides amongst the hills of Chianti, to long distance trips stopping in major cities from Todi to Florence to Siena to Pisa to Rome.

These three examples will hopefully help to inspire, but if planning isn't your thing then you could follow one of them to the day or let one of our Cycling Travel Specialists do some of the work for you – though not the pedalling bit!

Quick Tuscany

This route takes cyclists round the Chianti region on a quick six day spin between Pienza and San Gimignano via Siena.


Day One: Pienza 

Renaissance ideal Pienza's main treasures are the Duomo, with its slightly Germanic influence, the Palazzo Piccolomini and Palazzo Borgia.  After exploring Pienza loop around to equally charming Monticchiello – via the beautiful villa they used as the backdrop for the film 'The English Patient'.

Day Two: Pienza - Castelmuzio – Montepulciano 

The area around Pienza is white truffle country, but once you hit Castelmuzio, part of the crete senesi, the colours of the countryside change to soft greys with the clay.  

Day Three: Montepulciano – Mount Amiata  - Montalcino

This morning's ride cycles relaxingly downwards between the olive groves and grape vines, presenting you with a glimpse of the Radicofani tower.  Stop in Montalcino for lunch accompanied by a glass of Brunello.

Day Four: Montalcino Siena

The crete senesi expands around the other side of Montalcino as well, so you have to pass though it to get to the Monte Oliveto Maggiore Benedictine Monastery. 

Siena is today's final destination: Set on three hills, the city is drawn together by winding alleyways and steep steps.

Day Five: Siena – Chianti - Radda - Castellina 

Today's route heads up into the hills of Chianti, through Radda and on to Castellina. On a ridge between the valleys of the Arbia, Elsa and Pesa rivers, this medieval town has a massive fortress castle with a huge 14th Century tower.

Day Six: Castellina - San Gimignano

Tuscany’s San Gimignano is known for its architecture - a recognizable postcard image. As well as the architecture, the Collegiata and the People’s Palace carry significant art collections. 

Click though to the full Quick Tuscany Itinerary

North TuscanyPisa to Florence 

Day One: Pisa

Most famous for its leaning tower, Pisa is best seen at a walk rather than a cycle: a stroll around the Piazza del Duomo and the historic quarters could lead to the 12th century San Pietro a Grado or the magnificent Duomo.

Day Two: Pisa Circuit 

Leave your luggage in Pisa and head off into the pretty surrounding countryside. If you're feeling fresh take a spin UP the Monte Serra via the Certosa di Pisa Museum and monastery.

Day Three: Pisa – Calci – Mount Pisani – Lucca

9kms east of Pisa is the pretty commune of Calci, after which you'll start to catch glimpses of the peaks of Monti Pisani.  Once over the humps, cycle on towards Lucca, yet another charming medieval city with UNESCO World Heritage status.

Day Four: Lucca Circuit

Lucca is a good town to cycle round. Potential highlights include Lucca Cathedral, the Guinigi Tower  and the Villa Reale di Marlia. or an excursions to the lakeside town of  Torre del Lago.

Day Five: Lucca Altopascio - Vinci 

Leave Lucca bound 21kms ride to Altopascio, an important rest point on the pilgrims trail between France and Rome. After Altopascio the route skirts the edges of the photogenic marshes of Fucecchio before pulling in to Vinci.

Day Six: Vinci

Vinci is most famous for its most famous son: Leonardo da Vinci.  Despite the spotlight Leonardo brought down upon the town, it still looks much the same as it did in his day, surrounded by vineyards and olive groves. 

Click though to the full Northern Tuscany Itinerary

Southern Tuscany: Buonconvento & Pienza

Buonconvento Day One:  Buonconvento 

This pretty Tuscan commune with its small, well stocked museum of traditional Tuscan art and ancient enclosing walls is south of Florence and south east of Siena in the watercolour scenery of the crete senesi.  

Day Two: Buonconvento – Murlo – La Befa - Buonconvento 

Murlo's best features are quite different to Buonconvento's : it has the hill of Poggio Civitate – an ancient settlement being investigated for its archaeological value.  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.

Day Three: Buonconvento – Monte Amiata  – Montalcino 

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, lava dome: Monte Amiata.  

Today's cycle finishes in Montalcino, worth stopping at for the fortress, the Pallazzo Comunale and the delicious red wine: Brunello di Montalcino

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

It'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. 

Second stop on the day is another monastery, the Renaissance built Sant’Anna in Camprena Monastery, which is loved for its frescoes.  Another 16kms on is the final stop of the day: Pienza

Day Five: Pienza  - Bagno Vignoni Circuit

Though this itinerary isn'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 thermal springs town Bagno Vignoni

MontepulcianoDay Six: Pienza – Monticchiello - Montepulciano Circuit

Between Pienza and Monticechiello is a much photographed road that zigzags up and down a bright green hill between tall, narrow cypress trees. Beyond Monticchiello is Montepulciano of the red wine.

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

The 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 AgesSan Quirico d’Orcia still has the same medieval street plan it did when it became part of Siena midway though the 13th Century.  After lunch it's an easy cycle back to home base, the whole days cycle is around 34kms.

Click though to the full itinerary for this Southern Tuscany Cycling Tour 

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


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