5 Towns to Cycle through in Tuscany

Although Italy as a whole is a lovely place to visit, the region of Tuscany is perhaps the most beautiful.   With breathtaking scenery, delectable cuisine and fine wine and art to savor, it’s no wonder Tuscany has become one of the world’s most popular travel destinations.  This is particularly true for cycling enthusiasts, who delight in the rolling hills and mountain paths, which seem as if they were created for biking. 
Here are five towns in Tuscany that cyclists won’t want to miss.
Pienza
A UNESCO World Heritage Site, this quaint Tuscany town is sometimes referred to as the "touchstone of Renaissance urbanism”.  It is home to the piazza, which is defined by four main structures:  the Palazzo Piccolomini, which was the primary residence of Pope Pius II, the Duomo, a cathedral that dominates the center of the piazza, the Palazzo Vescovile, a retreat built for the bishops, and the Palazzo Comunale, the town hall of the piazza.  A cycle through this town is like a step back in time to the Renaissance era – a truly unique experience.
Montalcino
If it’s ancient architecture and rich history you’re seeking, then a ride through Montalcino should be on your itinerary.  One such architectural masterpiece is Il Castello di Montalcino.  Incredibly, the looming castle still remains virtually intact since its construction began in 1361.  Another fascinating landmark, located just 9 km from Montalcino is the Abbey of Saint Antimo.  Founded by the emperor Charlemagne, it’s one of Italy’s most beautiful churches to date.  And if the exquisite architecture isn’t enough, Montalcino is also home to a popular fine red wine known as Brunello di Montalcino.  It provides a lovely way to relax after a long ride.
Montepulciano
This interesting little town is home to several famous structures, some delectable wines, and some rather unique traditions.  Its center, the Piazzo Grande, is quite impressive with its surrounding houses and massive central tower which offers spectacular views of the town below.  Visitors here can sit back and enjoy a taste of the town’s fine Vino Nobile di Montepulciano and Rosso di Montepulciano wines.  And those lucky enough to be cycling through in August may be able to witness one of Montepulciano’s most famous traditions – barrel rolling.  During what’s known as Bravìo delle Botti, representatives from each of the city’s 8 districts compete in rolling a heavy wine barrel 1.5 km to the Piazza Grande.  The winners get to keep the wine.  Perhaps the best part of this competition is that the celebration carries on for days following the big event. 
Siena
This delightfully charming city offers a virtual step back in time to those who pass through.  With its car-free atmosphere and ancient city wall still intact, visitors often muse that it seems time has somehow stood still in Siena.  The heart of the town, known as the Piazza del Campo, is lined with various restaurants and quaint cafés and is home to the famous fountain Fonte Gaia.  Siena also boasts a multitude of museums which are filled with unique pieces of art and offer a glimpse into the town’s culture and history.  If that’s not enough, the simple fact that there are no vehicles to contend with makes Siena a prime place to cycle.
San Gimignano
This popular Tuscan town offers visitors a taste of medieval times, with its city walls, huge gates and a multitude of narrow alleys and pathways.  Its buildings and roads are very well maintained making a visit here quite pleasant.  So lovely is San Gimignano that it was named a UNESCO World Heritage site in 1990. It’s also known for the popular white wine produced there called Vernaccia, which was the first Italian wine to be awarded Denominazione di Origine Controllata (DOC) status.  If you happen to cycle through San Gimignano, be sure to take a break and visit the Town Hall’s tower.  The views are simply magnificent.

With its picturesque landscapes, countless historical sites and exquisite fine wines, Tuscany is easily considered one of Italy’s gems.  Its breathtaking coastline, rolling hills and intricate mountain paths, coupled with the rich history and fascinating encounters make a trip there a truly unforgettable experience.  If you’re planning to cycle through Tuscany, be sure these five towns are on your itinerary.  They truly encompass what Tuscany is all about and offer visitors a taste of the very best this region has to offer.