The three most common reasons people choose Tuscany as the backdrop to their travels are the uniquely coloured landscape, dotted with reason two: beautiful medieval hilltop towns famed for their architecture and the art displayed within them, and three: the food and wine. It's a region that ticks the Culture, Aesthetic and Lifestyle boxes and if you opt to see it by bike then you can tick the Active box as well.
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 well 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 are an excellent picnic spot.
On your way back into town you might find Pienza's streets bumpy – well they are cobbled, laid by medieval planners - but it's really pretty and the cafes are idyllic Italian, so it's worth spending another night in Pienza fuelling up on peddling fuel.
Start out into the colourful countryside again, cycling either the main roads or the back roads, and cycle past the olive groves into the white truffle country near Castelmuzio, part of the crete senesi, where the colours change – the clay here, instead of being warm red shades, is more grey, which is why the region is sometimes likened to a lunar landscape. Up and over Castelmuzio's hill the final destination for today's cycle is Montepulciano.
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 are as famously well endowed, either with beauty or wine quality as Montepulciano.
On the architecture and scenery side the main attractions are the main square – made in the great tradition of lovely Tuscan main squares - 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.
Out of Montepulciano, this morning's ride cycles relaxingly downwards, presenting you with a wonderful view of Mount Amiata, a dome of lava and Tuscany's highest point, and a glimpse of the Radicofani tower on the way. The country here is dotted with chestnut trees – in between the olive groves and grape vines of course, and the old volcano is still active enough to fuel the hot water bubbling up round the spa towns of Bagno Vignoni and Bagbi San Filippo.
Try to arrive in Montalcino, for lunch, and have a Brunello with it.
Even without being the town where the delicious red wine, Brunello di Montalcino, is made, this town deserves a little attention on a trip though Tuscany. There's been a settlement 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 man made structures is the view – over Asso, the Arbia valleys and Ombrone: a view over olive groves, vineyards and orchards, as well as a selection of pretty red stone hamlets.
The wine is made only of Sangiovese grapes, usually aged for a number of years (minimum of three) in hard oak barrels – and because of that it's always been quite a rare, and thus prized, thing. The wine growing region around this town is the warmest and driest in all of Tuscany, which is why the wine is distinctive. Wines from the northern slopes ripen more slowly and are more aromatic, and wines on the southern slopes are some of the fastest to ripen in all of Tuscany and are known for their complexity of flavours – partly also to do with the complex terroir. These days many local vineyards grow grapes on both the north and southern slopes. The name translates to 'nice dark one', which is a very fair description – experts tend to describe them using flavours like blackberry, black cherry, black raspberry, chocolate, leather and violets.
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. This is one of the largest monasteries 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 called Madonna with Child and Two Angels to get inside, where there's a medieval style palace built of the same red bricks, and a large quadrangular tower.
The 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.
After appreciating the art it's time to appreciate the landscape and then the architecture again in Siena. Surrounded by olive groves and the vineyards of Chianti, Siena is one of the most beautiful cities of Tuscany. Set on three hills, the city is drawn together by winding alleyways and steep steps, whilst the Piazza del Campo stands at its heart, and the Duomo (with its own museum next door) and St Maria della Scala serve as additional cultural landmarks. Siena also has one of the oldest Universities in Europe, which ensures a vibrant Italian student atmosphere throughout the academic year, in addition to the bustling daily life of this city's streets, squares and gardens. So there's plenty to do here if you want to extend your trip for a few days to relax after your ride.
Day five takes you up into the hills of Chianti past rows of olive trees and grape vines and tall cypresses, on roads winding past some of the regions best wine producers: Schiena d’Astino, Brunelli and Siro Pacenti for Brunello de Montalcino, Del Cerro and Boscarelli for Montepulciano and Fonterutoli, Antinori and Castello de Brolio for Chianti. Beyond Radda is Castellina (where it's a good idea to do a spot of wine tasting.). On a ridge between the valleys of the Arbia, Elsa and Pesa rivers, this medieval town has a few more major sights than it's equally charming fellows – a massive fortress castle with a huge 14th Century tower, now the home of an Etruscan museum, two lovely palazzos, the Via delle Volte vaulted underground passages, the Church of San Salvatore which has an early 15th Century fresco of the Madonna with Child, and the Romanesque church of San Martino.
Tuscany’s San Gimignano is known for its architecture, and provides a recognizable postcard image all over Europe – the fourteen 13th Century towers give the walled town a one-of-a-kind medieval skyline. In addition, the Collegiata and the People’s Palace carry significant art collections. You should also sample a glass of San Gimignano’s famous Vernaccia wine, a trademark of the town since the 13th century. The perfect place to finish your cycling soft adventure is in one of hilltop San Gimignano’s cafes, over looking the beautiful Tuscan view falling away beyond your glass of Vernaccia.
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