Exploring the Charming City of Siena on Foot: The Highlights

When it comes to the most popular things to do in Chianti, a visit to the utterly captivating hilltop city of Siena comes very high on most people’s list. Steeped in history and filled to the brim with magnificent architecture, for those who surrender to the charms of this ancient gem, the rewards are many and memorable.

Like lots of places in Italy, the very best way to explore Siena is on foot – and, in fact, for the most part you’ll have no choice as much of it is pedestrian only. For a lot of visitors, time is short when it comes to fitting in all the fabulous things to do in Chianti, so it pays to know the most important highlights not to miss.

If you’ve only got half a day to spend, here are the top must-sees in Siena.

Top Attractions of Siena

It doesn’t matter what order you see the highlights, and in fact it’s possible to stumble across quite a few by accident. Some are out of the way and some of them are impossible to miss. Step out and discover the secrets of Siena…

Piazza del Campo 

The main square of the city is instantly defined by its unique shell shape and configuration of bricks. As well as the imposing Torre del Mangia (climb it if you dare and get breath-taking views), the beautiful Fonte Gaia holds court over the throngs of locals and tourists taking coffee, lunch or dinner in any of the many cafes and restaurants that line the piazza. But its most distinguished claim to fame is its role as the site of the famous annual Palio horse race, and if you’re fortunate enough to be in Siena to see that, you’re in for the experience of a lifetime. 

The Duomo 

Virtually every Italian town or city has a cathedral, but there are none quite like this one, with its highly distinctive striped marble exterior. Even if you don’t have time to go inside it’s worthwhile wandering around taking in the beauty and majesty of the outside, but if you do have time, however, the interiors are as mind-boggling as the façade, filled with priceless Renaissance frescos and paintings. The massive dome itself is no less impressive for being unfinished and this is one of the most visited sites in the city. If you’re an art lover, don’t miss the Museo dell’Opera del Duomo, situated right next door.

Fortezza Medicea

The history of this ancient fortified city emanates from every hidden corner and backstreet, but to truly get a sense of the glory and turbulence of its days gone by, a visit to Fortezza Medicea is inspiring. Constructed in the sixteenth century, it serves as a symbol of the power Florence wielded over Siena after its final defeat. Today you can visit the fort and get some lovely views of the city.

Monte dei Paschi

History buffs will appreciate a visit to the oldest bank in the world, which is situated just a short distance from the fort in Piazza dei Salimbeni. The bank dates back to 1624 and its ornate fourteenth-century Gothic exteriors are as impressive as its long heritage. 

There are so many more attractions to discover in this incredible city and, even as you walk from one of these to another, you’ll encounter a host of history, culture, art and architecture. If on your itinerary of the best things to do in Chianti you only have half a day to spend here, the upside is that you’ll definitely have to come back…

Author Plate

Mauro Bramante is the Director of WalkAbout Florence, an independent business offering unforgettable tours and excursions around Italy including the best things to do in Chianti. Whether you want to ride a Vintage Vespa, try the famous Chianti wine or get cooking with fresh local ingredients, Mauro's company promises excitement, adventure and above all, fun. If you're keen to experience the magic of Italy with the help of some passionate and knowledgeable tour guides, look no further than WalkAbout Florence for your next getaway.