How To Use Your Free Time in Siena


When it comes to day trips from Florence, a visit to charming Siena should be top of the list. As captivating as it is stunning, this picture perfect city that will have you reaching for the camera as soon as it comes into view, breathes romance along every cobbled street and through every elegant piazza. Terracotta rooftops grace the skyline, offering the perfect contrast to the surrounding verdant vineyards, while in the centre of this beautiful place, architecture soars and monuments of a spiritual and a secular nature abound.


Well known as the home of one of Europe’s most magnificent representations of Gothic architecture, ‘il Duomo’, Siena is also famous for hosting the world recognised horse race, ‘il Palio’. While it is unlikely that you will see the race on day trips from Florence, the importance of what it represents is evident throughout every part of the city. Siena is divided into different contrade (districts) and people remain very loyal to the contrada of their birth. The horse race, which was inaugurated in the seventeenth century, is run with a horse from each district. Everyone, from the children to the grandparents, gets involved and there is much emotion as the anticipation of the race heightens. The winning horse is celebrated and paraded through the streets before being presented at the cathedral; it is a sight to behold - I have been there and I know!

When you book onto our Tuscany in One Day Tour you will have the chance to visit this glorious city, with its shell-shaped main square, known as Piazza del Campo, and its majestic cathedral. You will also have the chance to enjoy some free time to explore on your own, and while you might just want to people-watch and soak up the atmosphere in the sunshine, if you want to make the most of your free hour or so, we have some suggestions that will get you inspired.

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Top Tips for Free Time in Siena

Toss a Coin into Fonte Gaia

On organised day trips from Florence you will have a local guide accompany you, and when they leave you to enjoy your free time in Siena, they will no doubt set you off in the wonderful Pizza del Campo. Head to the top of the ‘square’ and you will find the intricately elaborate Fonte Gaia, or ‘Fountain of Joy’. Historically, this majestic water feature was built to replace an original pagan fountain that was blamed for the horrific number of fatalities caused by the Black Death, in 1348. The depictions of Madonna and Child, Adam and Eve and the cardinal virtues on the fountain you see today are replicas of the originals that were sculpted by Jacopo della Quercia in the fifteenth century, but they are still worth admiring.

Top Tip: Why not follow the tradition and make a wish and toss a coin into the fountain, like many have before you?

Take a Walk Around the Historic Centre

The best way to see a city is by getting lost, following your nose and taking random turnings up tiny streets to see where they lead. Siena is an open museum and no matter where you wander, there will be something to capture your gaze and hold your interest. Steep alleyways wind round unexpected corners and narrow little passages open up onto delightful squares adorned with magnificent architecture and quaint churches; head to Piazza Salimbeni where you can see the offices of one of the first banking establishments in Europe: The Banca Monte dei Paschi di Siena.

Top Tip: Hot foot it to the San Domenico Basilica, which is a Gothic church housing the preserved head of the patron Saint of Siena (Saint Catherine) - very weird but a wonderfully intriguing addition to day trips from Florence!

Climb the Torre del Mangia

A definitive rival to the cathedral when it comes to monumental highlights, this “Tower of the Eater” is a fourteenth century bell tower that rises 300 feet above the town hall. Interestingly, it was built to be the same height as the bell tower on the cathedral as a symbol that there was equality between the church and the state. I can highly recommend a steady climb up the many stairs for the wondrous views of the rooftops and the rolling Tuscan hills beyond; this is a real highlight of day trips from Florence that take in southern Tuscany.


Visit Porta Pispini

Standing strong as a walled city, Siena was a power to be reckoned with in its heyday. The Porta Pispini, which is also known as the Gate of the Water Spout, is located in the east of the city and is one of the few remaining gates dating back to the Middle Ages. It is a wonderful example of a defensive structure, with its stone double doorway, iconic arches and original wooden frames. Just to the right of the gate you can see the impressive guard tower and original protective walls.

Enjoy a Cappuccino and Pastry with the Locals

The cafe culture is rife in Siena and if you want to rub shoulders with the locals and indulge in a truly authentic atmosphere, head to Caffe Nannini. This is a veritable institution for coffee and its reputation for incredible pastries is totally justified. It is a great place to pass an hour, and somewhere you can just sit back and take a well earned break on day trips from Florence.

How To Use Your Free Time in Siena - 1

Stop by the Church of San Domenico

This imposing building, which is an amalgamation of different stylistic features, might not be much to look at from the outside, but the interior has some striking attributes. The chapel dedicated to the city’s patron saint is adorned with religious frescos as well as some marble additions. More ornate decor can be seen in the nave and the candelabras and altar pieces are also worth checking out.

Taste the Local Wines

Many wine bars offer ad hoc tastings of the quality local wines, and as you won’t need to drive on organised day trips from Florence, you’ll be free to indulge in a glass or two. Here are some of our favourites:

Enoteca Emporio Mediterraneo - Via Casato di Sotto

This is a hidden gem. Dating back to 1640, this incredible building is protected by the Belle Arti Ministry. It is actually part of the Palazzo dei Chigi, and here you can taste a fine selection of local wines and some vintages from the rest of Tuscany too.


Cantina del Brunello di Montalcino - Via della Sapienza

For a refined selection of Sienese wines, head to this historic wine bar just a stone's throw from the Piazza del Campo. The choice is vast and the bartenders are very knowledgeable. Why not grab a bottle or two to take home?

Cantina in Piazza - Via Stalloreggi

This is a great little spot for connoisseurs of wine. There are some of the best local vintages on sale here, alongside other regional produce, such as cheeses and salamis.

Shop, Shop, Shop!

Go to any Italian metropolis and shopping is always a pleasure - so this city is no different. Dotted between the charming grocery shops laden with fresh vegetables, cured meats and cellophane wrapped panforte, are classy designer outlets with window displays to rival those in any fashion capital. For wannabe foodies who love taking home a delicious souvenir or two, I can highly recommend a visit to Alimentari Danilel e Daniela in Via Sarrocchi, for an authentic Tuscan grocery shopping experience. Literally bursting with regional specialities, you will be treated to a feast for all the senses.


Pinacoteca Nazionale

If you need to get your fix of art when you visit the city, this museum is a great choice. In true Sienese style, the art is housed in a fourteenth century palace, Palazzo Buonsignori. Recently given a new lease of life, this museum, which was originally established in 1932, is now home to a fine collection of Gothic pieces. The works displayed show the clear difference in artistic styles that was so apparent at this time between Siena and Florence. While the latter was awash with Renaissance artists, the artists of Siena stuck faithfully to their Byzantine and Gothic techniques that were born in the thirteenth century. Consequently, many of the offerings here are religious and adorned with gold, which makes them very different to those masterpieces that were being produced only 70km to the north. That said, however, the exhibits you see at this museum are first rate and are beautiful examples of the art created in this city at the time.

Top Tip: You could stay all day here, but even in an hour you get the chance to get a feel for the place. Look out for Duccio's Madonna and Child, Bartolo di Fredi's enormous breathtaking Adoration of the Magi and Pietro Lorenzetti's Madonna Enthroned with Saint Nicholas and the Prophet Elijah.

Last But Not Least, Sample the Exquisite Gelato

Like most of this region, this city is famous for its wine, meat, pasta and ice cream. When you have a spare ten minutes there really is nothing more satisfying than enjoying a deliciously decadent Italian gelato. Don’t be lured by the expensive tourist traps when it comes to choosing your gelateria, but instead head to La Vecchia Latteria, an understated and reasonably priced hole in the wall that delivers the most incredible ice cream you could ever wish to taste. Made on the premises, the flavours are bursting with natural, seasonal and fresh ingredients. Every day new flavours are made so you never quite know what you might be offered.


While it is definitely worth seeing any new place on day trips from Florence with a tour guide, when you do get a chance to explore on your own, the city opens up on a whole new level. Siena is an easy place to navigate on foot and all roads lead back to the Piazza del Campo, so you can’t really go wrong. Whether you want to hang with locals, visit a museum, get that panoramic photo of the skyline or check out an art gallery, you will have time to do whatever is top of your list when left to your own devices.

We Are Walkabout Florence

Here at Walkabout Florence, we want all of our clients to get to know this magnificent part of Italy. History, culture, and especially the food and wine are ingrained in every part of Italian life and our guides and drivers are always keen to share their local knowledge. Florence is a wonderful city in which to be based if you are keen to get involved in any of our day trips, that include visits to Siena, Pisa and more. Book now, have a chat to one of our team, and start planning your next Italian adventure.

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