5 Reasons to Visit Siena on Your Next Tour

Riders cycling up a hill on the outskirts of Siena

Siena is the embodiment of a medieval city and one of the true gems of Tuscany. Built around the Piazza del Campo, the whole city sits atop three hills as a work of art that blends into the surrounding landscape. Approaching Siena and seeing it in the distance from the surrounding hills at sunrise is certainly one of the most magical views on a bike.

UNESCO listed for its historical authenticity, Siena’s significance as an Italian city was once due to its status as a key economic and trade centre during the renaissance. Centuries later it remains as one of the country’s most beautiful cities, truly loved and lived in by its locals.

It’s the passion of the locals that you experience when you are privy to an ‘insider’s visit’ and which puts this small city high on our most loved destinations in Tuscany, featuring on both our Tuscany Cycling Tour and L’Eroica Cycling Tour.

Below are the top 5 reasons we love Siena:

1. Siena’s history and sheer medieval beauty

Siena was a very important city in the middle ages. It’s position along the via Francigena, the important pilgrim route to Rome, saw it rapidly develop as an enterprising agricultural, manufacturing and mercantile bourgeoisie, as well as a lucrative trade hub for bankers. In less than two centuries, it grew to be one of the largest European cities. However the city’s rapid expansion triggered a lively rivalry with neighboring Florence that marked the history of Siena for 400 years. Siena’s glorious era can still be felt in every piazza and every street today and its rivalry with Florence still heard when talking to the locals; in fact, it’s a great conversation often shared around our dinner tables with locals on our Italian Cycling Tours in Tuscany.

2. Siena’s surrounding riding landscape

As you head south to Siena on the Strade Bianche as part of our L’Eroica Cycling Tour, you glide along the gravel in the early morning light with Siena in the distance, bathed in the first golden rays of sunrise. The sheer beauty of this scene is a memory that will stay with you forever.

One of our other favourite rides is when we leave Siena and head south towards the Crete Senesi towards Asciano. Enjoyed on our Tuscany Cycling Tour, the sparse lunar-like landscape is very special to ride through, with its dramatic terrain unlike any other in Tuscany.

the historic displays inside a contrada in Siena

3. Siena’s famous Palio & inside a Contrade Museum

Twice a year, on July 2 and August 16, Piazza del Campo hosts the Palio, a horse race between its contrade or city districts. It is one of the most ancient popular events in Italy, dating back to the Middle Ages, and is experienced with full participation by the Sienese as it is a catalyzer of intense passions and rooted in the soul and history of Siena.

Aside from being there to experience the real spectacle of one of the races, another amazing experience is having a local Sienese take you through one of the Contrade’s Museums. Our non riding partners on both our Tuscany Cycling Tour and our L’Eroica Cycling Tour get to experience this very special ‘behind the scenes’ tour which always leaves a deeply lasting impression of how special this deep rooted cultural event really is. It makes us Melbournians who revere the Melbourne Cup feel very underdone when considering the deep history.

The campo di Siena

4. Navigating Siena’s Cobblestone Streets

Riding through Siena’s rabbit warren of cobblestone streets as part of our Tour of Tuscany is quite an experience, before taking one final turn to arrive in the Piazza del Campo, the heart of Siena. We stop here for a coffee and opportunity to soak in the ambience and enjoy the beauty of this medieval masterpiece. Strictly speaking, you are not supposed to ride in the centro storico of Siena, which is due to the many people on the street, so it is a very slow game of “dodge the tourist” as you gently roll down the knoll.

ricciarelli composition

5. Delicious Sienese desserts

Siena’s food speciality are its rich desserts filled with the spices merchants would bring back with them from the Far East during the Renaissance.

• Panforte or Panpepato: firm but soft, this is made of honey, sugar, dried fruit and candied fruit, with lots of spices added; the dark colour, due to the spices and at times the cocoa covering it, distinguishes it from the less strong Panforte Margherita, dusted with confectioner’s sugar, and created in 1879 for Queen Margherita’s visit to Siena.

• Ricciarelli; tender biscuits made of almonds, sugar, egg white, vanilla and orange rind.

• Cavallucci; roughly shaped, these were at one time offered in the stations where travelers would change horses. They are firm but soft, rich in honey, candied fruit, walnuts and flavoured with anise and cinnamon.

Following a number of tastings by our groups on different tours, we think the Cavallucci may be narrowly pipping the Panpepato to the line as the favourite!

If you’d like to come and try these delicious morsels and experience the beautiful city of Siena for yourself, join us on with our Tour of Tuscany Cycling Tour or L’Eroica and Tuscany Cycling Tour.

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