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  • Writer's pictureGuidemyvoyage

Countryside day trips from Siena to explore the best of Tuscany

Updated: Apr 7


day trips from Siena. View of Tuscany landscapes

Siena is a fortress and medieval walled city surrounded by the stunning countryside of Tuscany. Siena is located in the centre of the Tuscan region close to the beautiful hilly landscapes of Val d’Orcia and Chianti that you may have seen on Instagram or in the movies.

The day spent in the Tuscan countryside is always dreamy especially if you combine it with visits to medieval Tuscan villages on the top of hills surrounded by a magnificent panorama of lush green hilly landscapes. The Siena is also surrounded by legendary wine-making villages like Montalcino where the iconic wine Brunello di Montalcino still dominates the world of red wine. Also, a village like Montepulciano and the countryside of Chianti produces some of the fine-class red wines that are popular worldwide. Therefore, a day spent in such legendary vineyards and admiring the history of winemaking following a visit to a historic village is an unforgettable experience.

In this article, we have mentioned magical day trips from Siena to explore the countryside of Tuscany and beyond. We have mentioned in detail everything you need to know including the best destination that can be visited as a day trip from Siena, how to spend a perfect day in such wonderful destinations and how to reach including the details of public transport.


So let's begin exploring the Tuscan countryside as day trips from Siena!


1. Day trip from Siena to Pienza 

day trips from Siena. View of Siena alleyways

From all other day trips from Siena, a day trip to the Medieval village of Pienza surely has to be on the top of the list due to its magnificent settings surrounded by beautiful Tuscan landscapes.

Pienza is a most beautiful hamlet located on the Tuscan hills of Val d’orcia surrounded by the magnificent panorama of beautiful, lush green hilly landscapes. Pienza is a medieval village recognised as a UNESCO World Heritage site in 1996. Later in 2004, its surrounding landscapes of Val D’Orcia were also recognised as a UNESCO World Heritage site. Pienza village was constructed by Pope Pius II in the 15th century and is known for its advanced urban planning of the 15th century. In the present day, the Pienza village has still maintained its charm of medieval times. As soon as you enter the walls of the village, it will give you a feeling of being in another time.

For a day trip from Siena, you can explore the Pienza village on foot including its picturesque old streets, Piazza Pio II, Palazzo Piccolomini, and Duomo di Pienza and walk alongside the walls of Pienza to have a panoramic view of the surrounding landscapes.

You can also spare some time to jump into the countryside and explore the picturesque surroundings. It's not always easy to explore the surrounding landscapes on foot, therefore, it's better to have a car, e-bike or a Vespa to explore. If you are comfortable walking, then you can explore the nearby popular spots like a shooting location of Gladiator movie which is located just a kilometre away from Pienza village.

You can hire a Vespa or a bike from the vintage tours which is a rental agency located very close to Pienza. You can also join one of their tours to explore the surrounding landscapes. 

You can also book a guided e-bike tour to explore the Val d’orcia landscapes from Pienza and jump to the Tuscan hills.

Pienza is also popular for its delicious Goat milk cheese called Pecorino. It is widely used in authentic Tuscan dishes. You can also visit one of the dairy farms that produces the pecorino cheese on the hill close to Pienza where you can taste the delicious freshly made Pecorino Cheese.


How to reach Pienza from Siena:
By Car:

Pienza can be easily reached by car from Siena Via SR2 road. The picture-perfect drive through the wonderful Tuscan landscapes all the way to Pienza takes around One hour from Siena. The car is always a recommended option to explore the countryside of Tuscany. There are multiple car parks available in Pienza and usually, you will find parking without any issue.


By Bus/Trains:

Pienza can be reached from Siena by a combination of Train and the bus. You need to board the Regional Train from Siena to Buoncanvento and then change to bus number 112 from Buoncanvento to Pienza. You can also catch the bus line 112 from Siena to Buoncanvento but it has very limited frequencies, therefore, it’s better to go by train. The overall journey will take around 1 hour and 15 minutes. Remember that the buses do not operate on Sundays. Therefore, always check the bus and train timing if you are dependent on public transport.



By Guided tours:

Guided tours operate from Siena to Pienza accompanied by a Knowledgeable guide and transport by private vehicle. If you do not have a car and want to have stress stress-free experience without worrying about public transport, then you can join this guided day trip from Siena to Pienza with visits to the Pecorino cheese farm and a delicious 3-course meal.



2. Day trip from Siena to Montepulciano.

day trips from Siena. View of Montepilciano

A few kilometres away from Pienza, the village of Montepulciano is another Gem located in the heart of Tuscany surrounded by stunning landscapes. Montepulciano is a walled medieval village situated on the hills of Tuscany standing at 2000 feet high. Montepulciano is also a popular wine-producing region in Tuscany producing some popular wines like Rosso di Montepulciano, Vino Nobile di Montalcino and Novello. Montepulciano is also home to some of the medieval architectural marvels like Duomo di Montepulciano, Palazzo Comunale and Palazzo Tarugi. 

Duomo di Montalcino is a church located in the village centre and the main place to worship in the village. The church was built in the 15th century and maintained its old charm in the present day. A few meters away from the Duomo, the Palazzo Comunale is a palace built by an architect named Michelozzo in the 14th century. The palace was inspired by the Palazzo Vecchio of Florence and therefore built as a replica of the Palazzo Vecchio of Florence.  Also, Palazzo Tarugi is another popular architecture built completely with the travertine and deserves a visit.  

If you are interested in the art collection and history of the region, then you can also visit the Museo Civico di Montepulciano which has a wide collection of archaeological findings and renaissance art.

Finally, during your day trip from Siena, reserve some dedicated time to visit the wine cellars and taste the famous wines of Montepulciano.  The village of Montepulciano has some of the very old typical underground wine cellars still functioning in the present day. The visit to such wine cellars is truly an amazing experience. It's always better to book the trip to wine cellars online to ensure your slot.



How to reach Montepulciano from Siena:

By Car:

Montepulciano can be easily reached by car from Siena within one hour via road SS715 surrounded by wonderful hilly landscapes. You will also find ample space for parking at the entrance of the village.


By Bus/Trains:

Montepulciano can be reached from Siena by a combination of Train and bus. You need to board the Regional Train from Siena to Buoncanvento and then change to bus number 112 from Buoncanvento to Montepulciano. You can also catch the bus line 112 from Siena to Buoncanvento but it has very limited frequencies, therefore, it’s better to go by train. The overall journey will take around 1 hour and 15 minutes. Remember that the buses do not operate on Sundays. Therefore, always check the bus & train timing if you are dependent on public transport.



By Guided tours:

If you don’t have a car, then the best option to reach Montepulciano from Siena is to join the guided tours from Siena. With guided tours, you don’t have to worry about transport and your guide will take you to all the best places in the region.



3. Day trip from Siena to Montalcino:

Day trips from Siena. View of Montalcino

Montalcino is another popular wine-producing region in Tuscany and perhaps one of the most popular ones from all over Italy since it produces one of the world-class red wines called Brunello di Montalcino. Like other popular villages of Tuscany, Montalcino is also a village situated on the hills surrounded by picture-perfect green landscapes full of vineyards, Olives, and Oak trees. The Montalcino is a picturesque walled village with colourful streets packed with wine shops, boutiques, cheese and glossary shops and restaurants.

Montalcino has so much to offer for the day trip from Siena. You can spend a day strolling in its old town centre, exploring its historic landmarks, hopping in its vineyards, taking a tour of the wine cellars, testing the world-class Brunello from the cellar, and admiring the views of the wonderful typical Tuscan landscape of Val d’Orcia region.

The most popular landmark in Montalcino is its 13th century fortress called Rocca di Montalcino which also offers mesmerizing views of the surrounding Tuscan hills. Also, the town hall named Palazzo dei Priori is another architecture mainly popular for its clock tower and deserves a Visit.

Finally, a trip to Montalcino is incomplete without visiting the vineyards and testing precious Brunello di Montalcino straight from wine cellars. To visit the wineries, it is better to join the guided tours to the winery and wine tasting in Montalcino where the knowledgeable guide briefs you all the history of the Brunello di Montalcino and its legendary Journey. 



If you are not taking any wine tour, then You can also visit the small wine shops in the Montalcino to taste the wine by glass.


How to reach Montalcino from Siena:
By Car:

Montalcino Can be reached by car in around 50 minutes via highway SR2. The roads are surrounded by picturesque landscapes. You can also find parking spaces at the entrance of the old village. Car is the more preferred option for a day trip from Siena to Montalcino.


By Bus/Trains:

Montalcino can be reached from Siena by a combination of Train and bus. You need to board the Regional Train from Siena to Buoncanvento and then change to bus number 114 from Buoncanvento to Montalcino. You can also catch the bus line 114 from Siena to Buoncanvento but it has very limited frequencies, therefore, it’s better to go by train. The overall journey will take around 1 hour and 15 minutes. Remember that the buses do not operate on Sundays. Therefore, always check the bus & train timing if you are dependent on public transport.  



4. Day trip from Siena to San Gimignano

day trips from Siena. View of San Gimignano

San Gimignano is a Jewel of Tuscany which closely resembles what medieval-era Manhattan would look like. The walled village of San Gimignano is widely known for its Medieval towers which contemplated as a symbol of power and wealth during medieval times. In the present day, a total of around 14 towers standing tall since the centuries can be seen in the village.  

San Gimignano is an old city built in the Middle Ages and still in the present day, the charm of the Middle Ages is well preserved. As soon as you enter the walls of the village, you will be surely travelling back in time since everything seems so old and unreal. No wonder the village of San Gimignano itself is listed as a UNESCO World Heritage site.

The village is full of medieval architecture. Some of the popular sites to visit in San Gimignano are Piazza Duomo, Duomo di San Gimignano, Piazza Cisterna, town hall or Pallazzo Communale, Torre Grossa and its colourful old streets packed with boutique shops.

San Gimignano is surrounded by lush green landscapes full of vineyards. Vineyards around San Gimignano produce a popular white wine called Vernaccia di San Gimignano. Therefore, a day trip from Siena to San Gimignano would be incomplete without visiting its Vineyards and tasting its delicious Vernaccia di San Gimignano.



How to reach San Gimignano from Siena
By Car:

San Gimignano is just 40 KM away from Siena and can be reached in less than 45 Minutes by car via highway Raccordo Autostradale Firenze – Siena. There are multiple options in San Gimignano for paid parking and you will easily find the slot. Car is a preferred option for a day trip from Siena to San Gimignano.

 

By Bus/Trains:

To reach San Gimignano from Siena, you can either reach by a combination of bus and train or by direct bus from Siena. The preferred option is to take the direct bus line 130 from Siena to San Gimignano. Or else, you can take a train from Siena to Poggibonsi and then change to bus number 130 from Poggibonsi to Siena. The bus 130 departs from Siena as well as from Poggibonsi.


By Guided tours:

If you don’t wish to have the hustle of public transport, then guided day trips from Siena to San Gimignano would be the best option. The guided tours offer transport by private vehicle and are accompanied by knowledgeable guides.



5. Day trip from Siena to San Quirico d’Orcia

day trips from Siena. View of San Quirico d’orcia

The lesser-known gem of Tuscany, the San Quirico d’Orcia is located in the heart of Tuscany and surrounded by magnificent picture-perfect landscapes. The San Quirico d’Orcia village is nestled on the hills of Tuscany and hidden between the popular villages of Pienza and Montalcino in Val d’Orcia valley.

San Quirico d’Orcia is also a Medieval village and its Medieval walls and architectures are still intact in the present day.

The main attraction to visit in San Quirico d’orcia is Collegiata di San Quirico which is an 8th-century church (later reformed several times), Santa Maria Assunta which is also an 11th-century church, and our favourite one the Chapel of Modenna of Vitaleta. The Chapel of Madonna of Vitaleta is a unique site located just 3 Kilometres away from San Quirico d’Orcia centre. It is a very small chapel located in a wonderful and picturesque setting surrounded by jaw-dropping views and naturally framed by cypress trees which makes it unique and therefore, should not be missed if you are visiting San Quirico d’Orcia.    

You can spend a wonderful day in San Quirico d’orcia simply by strolling through its picturesque streets, visiting its medieval architecture, exploring the beauty of Chapel Modenna of Vitaleta and admiring perhaps the best of Tuscan landscapes than any other village has to offer.  


How to reach San Quirico d’Orcia from Siena
By Car:

A car is a preferable option for a day trip from Siena to San Quirico d’Orcia. The 46 KM drive will take around 1 hour to reach San Quirico d’Orcia from Siena. Perhaps it would be one most beautiful drives of your life since the road passes through the beautiful hilly landscapes of Val d’orcia. There is also an ample parking space available just at the entrance of the village.


By Bus/Trains:

San Quirico d’Orcia can be reached from Siena by a combination of Train and bus. You need to board the Regional Train from Siena to Buoncanvento and then change to bus number 112 from Buoncanvento to San Quirico d’Orcia. You can also catch the bus line 112 from Siena to Buoncanvento but it has very limited frequencies, therefore, it’s better to go by train. The overall journey will take around 1 hour and 15 minutes. Remember that the buses do not operate on Sundays. Therefore, always check the bus and train timing in advance if you are dependent on public transport.



6. Day Trip from Siena to Volterra

day trips from Siena. View of Volterra

Volterra is another best-kept secret of Italy hidden in the hills of Tuscany. It is a true Gem not known to many people travelling to Italy, especially Tuscany. Volterra is also referred to as the Sister of San Gimignano since it is also an old and walled city with the well-preserved charm of the medieval ages.

If we talk about a little history of this village, Volterra was one of the most important cities of ancient Etruria (Etruria was a small country that flourished civilisation between the 8th and 3rd centuries BC). Later, it was conquered by Rome in the 3rd Century BC.  Voltera was and is popular for the alabaster and therefore, the village of Voltera was also popular for Alabaster Artifacts crafted by local artists which was preferred especially by Romans.  

As soon as you enter the walls of Volterra, you will definitely travel back to Ancient Ehturia since the atmosphere still maintains the old touch of ancient times. The village of Volterra has so much to offer during the day trip from Siena including the visit to its well-preserved old Architecture like Palazzo dei Priori located on the square Piazza dei Priori, the Roman Theatre, the cathedral of Volterra and the city walls. You can also visit the Etruscan Museum of Volterra which houses collections of fine artefacts from the Etruscan era especially the ones crafted with alabaster. At the Palazzo dei Priori, you can also climb the tower and admire the magnificent panorama of the Voltera and surrounding landscapes.


How to reach Volterra from Siena:

By Car:

You can drive to Volterra from Siena in 1 hour via SS 68. It is around 57 kilometres away from Siena. There is ample parking space available just outside of the city walls. A car is always a preferred option for a day trip from Siena to Volterra if you are visiting on your own.


By Trains/Buses

Reaching Volterra from Siena by public transport is quite a hustle and needs precise planning due to the limited frequency of the buses. To reach Volterra from Siena, you need to catch bus number 130 from Siena to Colle Val d’Elsa. From Colle Val d’Elsa you need to change to another bus number 770 to Volterra. Bus number 770 has very limited trips per day. Therefore, plan your journey accordingly.  Remember to check bus timetables in advance before planning a day trip from Siena to Volterra.



By Guided tours

If you don’t have a car, then we recommend joining a Guided tour to Volterra to avoid the Hustle of public transport. The guided day trips from Siena cover both Volterra and San Gimignano together and offer transport through private vehicles.



7. Day Trip from Siena to Monteriggioni

day trips from Siena. View of Monteriggioni

Nestle in the Countryside of Chianti, the Monteriggioni is another Gem of Tuscany located close to the Siena. It is a very small walled city built in the early 12th century with no more than 20 structures or houses. The small village also has a square called Piazza Roma which houses its own Romanesque church called Santa Maria Assunta. The village is very small that you can walk the circle of the village in just 10 minutes. The circumference of the wall is just around 570 meters in length.

The village of Monteriggioni was situated on the conflicted territory between the reigns of Siena and Florence in medieval times. The fortification of the villages was done to safeguard them from the reigns of Siena and Florence. The walls of Monteriggioni village even have 14 encircled towers to keep an eye on the enemies from any direction. For the day trip from Siena to Monteriggioni village, you can explore the village, its walls, its church and finally you can also explore the Museum of Armoury which has collections of medieval and Renaissance weaponry.

Exploring the whole village will take only a couple of hours. Therefore, we recommend combining your day with a visit to the wineries of Chianti to understand the process of world-famous Chianti wines and taste their wines from the wine cellars. The winery named Tenuta Villa Trasqua is just 5 kilometres away from Monteriggioni which can be visited after a visit to Monteriggioni. However, to get there, you would need a car. 


How to reach Monteriggioni from Siena
By Car:

Monteriggioni is located very close to Siena (Only 15 km away) and can be reached Via SR2 highways in just 20 minutes. Car is more preferred option for a day trip from Siena to Monteriggioni.


By Bus:

Monteriggioni can be easily reached by bus from Siena. The bus lines 131, 130 and 136 stop at bus station Colonna Di Monteriggioni and from there you can walk for around 700 meters to reach the village.


By Guided tours:

If you don’t have a car then we recommend exploring Monteriggioni with guided tours since along with the visit to Monteriggioni, they also take you to the best wineries in Chianti which is not possible to visit by public transport.



8. Day Trip from Siena to Assisi

day trips from Siena. View of Assisi

Assisi, perhaps a little far from Siena, but can comfortably visited as a day trip from Siena by car. Assisi is a religious pilgrimage town in Italy owing to the birth of the patron saint and poet, Saint Francis of Assisi in 1181. Saint Francis was the one who founded the religious order of the Franciscans. He was born and lived in Assisi and is known for his selfless deeds for poor and underprivileged people.  

He was one of the most valued saints of Christianity and therefore, the Assisi holds utmost importance in the belief of Christianity. The Basilica of Saint Francis was built in Assisi after the death of Saint Francis in 1228. Some relics of Saint Francis of Assisi are also stored in the Basilica which is another reason for The Basilica of Saint Francis being an important pilgrimage site of Christianity. It is also listed as a UNESCO World Heritage site.  

Apart from its religious importance, Assisi is also a beautiful medieval town located on the hills of Umbria which is a neighbouring region to Tuscany. Assis is also popular for its picturesque and nicely decorated alleyways, colourful shops, the Rocca Maggiore di Assisi which is a fort of Assisi and other well-preserved medieval architectures.

For a day trip from Siena to Assisi, you can visit the most popular Basilica di Saint Francis, then you can climb to the Rocca Maggiore di Assisi to get the mesmerizing views of Umbrian landscapes, later you can explore medieval architecture like Duomo di San Rufino, the church of San Domiano & Basilica di Santa Chiara and finally, you can end your day by exploring the hidden picturesque alleyways of the old town.

To learn more about the history of Assisi, you can also join the walking tour of Assisi with a local knowledgeable guide.


 

How to Reach Assisi from Siena
By Car:

Perhaps the only and the best option to visit Assisi from Siena is by car via highway SS 715. It is located around 135 KM away from Siena and the drive would take around 1 hour and 40 minutes.

There are no public transport connections to reach Assisi from Siena and also no Guided tours operate to Assisi from Siena.


9. Day trip from Siena to Florence

day trips from Siena. View of Florence

Last but not least, one of the most popular cities in Italy is not so far from Siena and can be comfortably visited as a Day trip from Siena. If you are visiting Siena then perhaps Florence already is in your Itinerary, if not then don’t miss to visit the city of Renaissance art as a day trip from Siena.

Florence is the city where Renaissance art was born and still hosts the most renowned Renaissance arts of history such as David of Michelangelo. It is also a city of one of the most renowned architectures in the world called the Duomo di Santa Maria Novella.

For the day trip from Siena to Florence, you can start your day by visiting the Duomo di Santa Maria Novella and climbing to its dome. Later, you can visit the Uffizi Gallery to admire the fine collection of Renaissance art including paintings and sculptures. After the Uffizi Gallery, head to the Piazza della Signoria and visit the Academia gallery to admire the most popular Renaissance art, the David of Michelangelo. After the Academia Museum, head to the Ponte Vecchio which is a picturesque old bridge housing the gold jewellery shops. You may already have seen Ponte Vecchio on Instagram or in Movies. Finally, after the Ponte Vecchio, climb up to the Piazza Michelangelo to admire the magnificent Panorama of Florence city and witness the magical sunset.

One day would not be enough to explore Florence in total. However, the main sights can be explored in one day comfortably. To avoid the waste of time in queues, make sure you book your entrance tickets to Museums in advance, especially the entrance to Uffizzi and Academia Museums because they are usually overbooked and at the last minute you may be able to find the entry slot.  



How to reach Florence from Siena:
By Car:

Florence is around 70 KM away from Siena and can be easily reached by car in one hour via the Main highways Raccordo Autostradale Firenze - Siena. In Florence city, you can find many Paid and free parking options.


By Bus/Trains:

The direct or one-stop regional trains continuously run between Siena and Florence. If you don’t find the direct train, then you need to change the train at Empoli to reach Florence. The train journey takes around 1 hour and 35 Minutes.

You can also reach Florence from Siena by Bus line 131 which also offers good frequency. The bus Journey takes around 1 hour and 30 Minutes.   


We hope that you liked this article and it will help you to plan a perfect day trip from Siena. If you have any questions about exploring Tuscany or any other places in Italy, then do not hesitate to Contact us. We will be very happy to help you. Please let us know your thoughts in the comments section.


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Guest
Apr 11

Very Helpful article. Thanks for sharing!

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