The best things to do in Siena and nearby for a Tuscan stay you’ll love

All you need to know to make the most of your stay in Siena: the best things to see in Siena, the best day trip in the Siena region, my recommendations for restaurants, accommodation and tours, based on my own travels.

The historical town of Siena is one of the most beautiful in Tuscany and a fantastic place to call home while vacationing in Tuscany.

Siena itself is hilltop town of medieval origins that managed to retain incredible integrity, so that you still very much feel like you are walking into a place from another time.

Siena old center is an extravaganza of tall towers, meandering streets, museums, shops, mouthwatering food, which that means the city is both an open air museum, yet a very real place.

Around it, the Tuscan countryside expands in the landscape that are most quintessentially associated with this region: the rolling hills, the cypress trees, the vines and the hilltop hamlets are all here!

I love the area of Siena and, if you have been onto this site before, you may have already heard me waltz lyrical about Val d’Orcia (the area with the rolling hills) and how I never tire of it.

Today, I though I would go more in depth about the area of Siena, since it is one I always recommend to use as a base. In this post, I recommend the best things to do in Siena town, accommodation I believe you will like and experiences worth trying in this area. I hope you enjoy it!

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Travel guide to Siena TL;DR

Visit Siena: The best things to see in Siena town

A trip to the area of Siena must include at least a one day visit to Siena itself, a jewel of medieval architecture and one of the best hilltop towns in the whole of Italy.

A visit to this pretty city is easy: Siena is compact and vastly car free and all it takes ti enjoy it is to leisurely stroll with your nose in the air. You don’t need an itinerary, however, it is handy to have a quick list of top sights to see.

💡 Top tip! While you do not need a tour to enjoy Siena, if you are interested in history and keen to learn more about what makes Siena special (for instance, the story of its contrade and the Palio), taking a walking tour like this one with a local guide that also includes Duomo entrance is a good idea.

In Siena, I recommend you seek out:

• Piazza del Campo is one of the most famous landmarks in Siena and one of the most beautiful piazzas in the whole it Italy. 

Located right in the heart of Siena, Piazza del Campo is a vast piazza with a peculiar shell shape. Its focal point is Palazzo Pubblico and its medieval tower Torre del Mangia, but the square fans out all around it, as it offering a cavea from where to admire it.

The palazzo is open to the public, tickets can be bough on the day or from the official online ticket office. If you are fit and not afraid of heights, you can also climb the tower: it is 87 meters tall and has over 400 steps but the view from above they say is stunning (as a person with a fear of height, I didn’t go but the photos are amazing!

The Piazza also has a fabulous fountain worth seeing: Fonte Gaia, carved with beautiful sculptures decorating its frame. As you take a sip from its refreshing waters, notice the detail of the water tray: it has the shape of a shell, the same as the square! 

The piazza is breathtakingly beautiful. As you come from the small and sometimes oppressive small side streets, it suddenly opens in front of you in a triumph of light and space.

Its ground has a distinctive orange/biscuit color and so do many of the buildings surrounding it and this gives the square a welcoming, warm feel.

• Duomo di Siena Only a short walk from Piazza del Campo you will find the other jewel of Siena, the stunning Siena Duomo.

The Duomo of Siena is one of the most important examples of the Romanic-Gothic style in Tuscany and beyond and one of the most churches in Italy. Its façade has beautiful golden panels decorated with intricate sculptures and it glimmers under the Tuscan sun. 

The bell tower has white and dark green  marble stripes, a color combination and a pattern that makes it almost unique in its genre, and it is sure to capture your attention (if you are visiting with young kids yes, they will scream ‘it’s a zebra!) and the inside is as impressive.

Inside the duomo, you will find again the dark green and white pattern of the towers, you will be to admire the works of art of many artists of the caliber of Donatello, Nicola Pisano, Pinturicchio and Michelangelo and you may even be lucky enough to be here when the Duomo’s floor is on show.

The pavement is decorated with 56 marble panes with carved an equal number of scenes and is an attraction in itself!

It is worth taking the time to visit the Museo dell’Opera del Duomo, inside the cathedral itself, to learn about the peculiar challenges and techniques this type of decoration posed to its creators.

• Santa Maria della Scala Just in front of the Duomo you will find Santa Maria della Scala, the old Siena hospital.

Hospital, in this case, means ‘place of hospitality’ and it was a location for the poor, abandoned children and the Pilgrims walking the Via Francigena to rest and regain strength. 

Santa Maria della scala is now a museum and it is worth visiting for the incredible spaces, frescoes and treasure it contains. 

In Siena, eat at: Taverna di San Giuseppe | La Finestra | Le Logge

Visit Chianti wineries

One of the best things to do in Siena’s region is to visit wineries and castles, two significant realities of this area and often occurring together!

The best way to visit these establishments is by car, if you have someone to act as designated driver, or by tour. Tours are expensive in this area but mean you can relax and all adults can drink so, if budget allows, they are a great resource! One I love is this one which is upscale, brings you to stunning wineries and makes you feel really pampered.

Wineries I recommend you check out are:

🍇 Castello di Ama Castle https://g.co/kgs/yptDwyS

🍇 Castello di Brolio Castle https://g.co/kgs/76zJbFn

🍇 Antonori cellars https://g.co/kgs/9jvX1vU

🍇 Castello di Verrazzano Castle https://g.co/kgs/9TXLZpf

🍇 Fattoria La Palagina Farm with winery (very kid friendly as it is also a farn ) Via Grevigiana, 4, 50063 Figline e Incisa Valdarno FI, Italy

• Tip if visiting with kids: wineries in Italy are kid friendly, they can just tag along! My favorite place for them is La Palagina but it is not the only one they are sure to enjoy. Find here >> my guide to going wine tasting in Tuscany with kids

Have a Farm to table experience Tenuta Chiudendone

A place I love near Siena is Tenuta Chiudenone, a private estate that opens its doors to visitors and offers a wonderful farm to table experience.

The experience is a whole day affair and the best way I can find to describe it is: imagine you have friends with an amazing house in Tuscany and they invite you over for the day. This is just what this experience feels like!

Francesco and Isabella are the owners here and they welcome you as an old friend: they offer you drinks, show you the estate (they have vines, olive trees, vegetable garden and forest areas), they then cook with you, have lunch with you, serve their food, wine and oil and then even offer the chance to stay and lunge in their pool area for the afternoon!

I love this experience because it feels really local and is a chance to immerse yourself in the countryside without stress or the need to figure out logistics or food (they can come pick you up). The experience is kid friendly!

You can find my full review here

Visit Bagno Vignoni (1 h drive) and its thermal pools

Bagno Vignoni is a thermal spring town in the province of Siena with something unique: in the center of town, instead of a church or municipal palazzo, it has a piazza entirely occupied by a pool of natural hot spring water (not to swim, to see only)!

The piazza is an absolute delight and very much the centerpiece of the ‘town’ which only consists of a few streets, developing arond this central point.

A visit to Bagno Vignoni doesn’t take long but it is delightful and different from pretty much anywhere else you will see while staying in this area.

My favorite way to visit is to go and spend the day in outdoor thermal pool of Hotel Posta Marcucci (kid friendly) or also go in the afternoon for aperitivo in one of the pretty establishments of this area.

Take a the scenic drive in Val d’Orcia

Val d’Orcia (Orcia Valley) is a stunning part of Tuscany and maybe the one place that, more than most, embodies the idea of Tuscany overseas visitors are most familiar with.

Here you have where the rolling hills, the cypress trees the olive groves that many associate with Tuscany and of course plenty of historic hilltop towns and vineyards to indulge in sightseeing, wining and dining.

Val d’Orcia is an area of great natural beauty with several centers worth seeing and it is best discovered by car. Stunning scenic drives here are along SP53, SP 146, SS2.

Places not to be missed here are Pienza, Vitaleta Chapel, San Quirico d’Orcia and Montepulciano. A lovely place to catch lunch with views is Podere il Casale. All easy to visit with kids too.

Eat lunch at: Podere il Casale | La Foce | Lupaia

You can find here >> my guide to Val d’Orcia | and here >>> the one specific about visiting Val D’Orcia with kids

Visit Montepulciano

Montepulciano is one of my favorite towns in Tuscany and a place I go back to over and over again.

The town is surrounded by mighty walls and has maintained its original urban structure, made of meandering roads and alleys climbing up the hill to the main town square.

This small town is one of the most beautiful you can see in the area.

Piazza Grande, at its very top, has a wonderful municipal palazzo, duomo and an impressive ancient well.

The views for the town towards the countryside below are breathtaking and surprising, making their appeared behind unassuming streets and alleyways.

If this wasn’t enough, the town is also famous for a warming, beautiful red wine called Vino Nobile di Montepulciano, a real treat for wine lovers!

Eat at: Caffe Poliziano (asl for a table near the window for the views)

Click here to read >>> my full guide to Montepulciano (also for families with kids)

Enjoy Pienza and the gladiator’s cypresses

Pienza is a wonderful, small hilltop center south of Siena and if looking at the photo you get a sense that the place is familiar, you’d be right: Pienza appears in a vast percentage of photos of Tuscany!

The photos usually focus on the lovely rolling hills you can admire form Pienza and the spot now known as “Gladiators’ Cypresses’, famous for being just what the name suggest: a Gladiator’s film location

However, Pienza has more than this.

The towns has ancient origins but during the Renaissance it went through a big transformation: Pope Enea Silvio Piccolomini, born here, enlisted the help of prominent artists of this time to make his place of birth into a beacon of Humanistic perfection.

Indeed, Pienza is lovely. The town is a picture perfect delight: the city center is make of adorable pretty streets with flowers on the windows and pretty corners and the main piazza is a marvel of Renaissance architecture.

Pienza’s Duomo is a wonder and the town has beautiful bastions that overlook the beautiful countryside around the town. If you are looking for a beautiful town in Italy, look no farther than Pienza, Tuscany!

Eat at: Podere il Casale (out of town)

You can find here >>> my guide to Pienza

Explore San Gimignano

San Gimignano is one of the prettiest and most visited hilltop towns in Tuscany and with good reason!

Perched on top of a beautiful hill, San Gimignano is a medieval walled town with a perfectly preserved old center, a staggering amount of medieval towers (it is not called ‘city of towers’ for nothing!) and it is also a lovely place for foodies.

As well as stunning churches and alleys, San Gimignano is famous for the production of saffron and the delicious vernaccia wine: vernaccia di San Gimignano.

The town doesn’t require long to see and is close to Siena, from where is a popular day trip.

A lovely way to visit, in my opinion, it to come here early in the morning, then have a late lunch in a nearby winery (Tenuta Torciano or Poggio Alloro for instance are very close to the town) and then complete the day with a second stop in Monteriggioni (see below).

Eat at: Fattoria Poggio Alloro, Le Vecchie Mura, Da Pode. Gelato from Dandoli.

Find our guide to San Gimignano here.

Discover Monteriggioni

Monteriggioni is a tiny village perched on the top of a hill in the province of Siena with something special: pretty perfectly deserved medieval city walls!

It is the quintessential Tuscan town, surrounded by imposing turreted walls and with views of rolling hills dotted by olive trees as far as the eye can see.

The town consists of a main square and a handful of streets, and can be visited in a short time: the best things to do here are the walks along the bastions (if you are not afraid of height), having lunch in the medieval square and peek at the local shops. We usually come here as an easy lunch stop or for evening aperitivo.

If you have kids, a stop at the local museum is fun as you can try on period clothes!

If you can, try and visit the city in early July when the Monteriggioni medieval festival takes place.

Find here >>> My guide to Monteriggioni

Explore Florence

Florence needs no introduction so instead of telling you why a day trip to Florence from Siena is a great idea (the art, the food, the shopping, the atmosphere…)

I will do more: I’ll share the itinerary that I believe till allow you to enjoy the best of Florence in just one day! Find it here Florence city center itienrary

Cycle around Lucca

Lucca is a wonderful small town in Tuscany, a gem of a places that manages to steal the heart of anyone traveling here!

The town has Roman origins and has been inhabited ever since the first dwellers made themselves at home here, and this means that nowadays you have in town several attractions from different historical times worth seeing.

The first thing many notice about Lucca are its walls: Lucca is still entirely surrounded by its walls and they are so beautiful and large, you can cycle on them! 

Cycling Lucca’s walls is one of the best things to do in this beautiful small town and a great way to get a sense of what Lucca is all about.

Aside from the walls, Lucca has a stunning main square that has been built of the ruins of a Roman amphitheater, of which you can stil guess the shape, and it also has many churches, so many, you may not believe they all fit in such as small city! 

Lucca is a delight to visit and is even special for music lovers since it was the proud birthplace of composer Puccini.

In Lucca, eat at: PepeRosa | Buca di Sant’Antonio

You can find here >>> my guide to Lucca | And here >>> my guide to visiting Lucca with kids (it’s lovely for them!)

What to eat in Siena area

Siena is famous for gorgeous foods and the main things to taste here are:

Pici con il ragu di cinghiale – pici is a type of pasta typical from the city of Siena. You can taste it with Tuscan Ragout or Wild Boar Ragout, both super tasty and typical of the area

Antipasto tipico senese – the Traditional Siena’s Appetizer is usually a platter with a selection of cured meats, local cheese and bruschetta with vegetable and meat pates. 

Cantucci col vin santo – at the end of a meal, cantucci col vin santo are a delicious treat. These are dry, rather hard biscuits with almonds served with a shot of sweet wine to dunk them in!

Colli senesi Chianti wine – Siena is surrounded by wine regions and you cannot go wrong ordering local wine. You can have Colli Senesi wine or pick one from the area just to the South of Siena, such as Rosso or Brunello di Montalcino, Morellino di Scansano or Vino Nobile di Montepulciano.

Where to eat in Siena and surrounding area

The area of Siena has outstanding food so it is hard to go wrong pretty much no matter where you go!

Some places that, in my opinion, may deserve a special mention are:

• Dario Cecchini’s Solociccia https://www.dariocecchini.com/solociccia/?lang=en
• Taverna Da Ciacco, San Quirico d’Orcia https://guide.michelin.com/ie/en/toscana/san-quirico-d-orcia/restaurant/taverna-da-ciacco
• Podere il Casale https://podereilcasale.com/en/
• La Lupaia https://www.lupaia.com/it/
• Castello di Verrazzano https://www.verrazzano.com/
• Castello di Meleto https://www.castellomeleto.it/

How to get around Siena and surrounding area; Where to Park

The area of Siena is best discovered by car as train and bus access to the surrounding area and country accommodation is limited.

Driving in this area is not hard and does not require any special vehicle; however, I recommend to try and avoid excessively large SUVs as these are harder to handle as you get close to the towns, where roads tend to get a little smaller. You can find here >>> my tips for driving in Tuscany.

The vast majority of Tuscan towns are not accessible by car, as the center is protected by a ZTL (limited traffic area). To avoid driving where you shouldn’t, follow the P signs for parking and leave the car in designated spaces, then explore on foot. You can find here >> my guide about parking in Italy.

I hope you enjoyed this guide to the best things to do in Siena and surroundin area and found it useful. Safe travel planning!