Top Day Trips From Siena
Siena is truly the heart of Tuscany which makes it a great base to do some side trips during your visit. Even if you don’t have a car, the top day trips from Siena Italy are extremely easy to reach by either bus or train and do not require joining a guided tour group. Within just an hour of Siena you can find Tuscany’s best hilltop villages, Medieval castles, classic wineries, breathtaking vineyards, and a few hidden gems you’ve never heard of before! Hope you enjoy our top day trips from Siena!
Transportation Info From Siena:
While you will want to avoid driving in some of the larger crowd cities in Italy, the side trips from Siena are very easy to reach by rental car. We love getting a car while leaving either Florence or Rome to explore the area around Siena for a few days. Being able to go at your own pace and see the countryside is amazing. Rental cars are cheap at about $25 a day, however, most auto and credit card insurance perks for rental cars exclude Italy so you will have to buy the additional coverage from the rental company.
If a rental car doesn’t fit into your plan you can still see most of the top day trips from Siena with direct connections by bus. The buses usually run starting very early and go into the night, plus the main bus station is right by Old Town Siena. There is a train station (here) further on the edge of Siena that can take you to places like Florence, but the bus is usually a lot faster, cheaper, and closer to town. We will explain how to get to each of the top day trips from Siena below.
Best Side Trips From Siena:
1. Florence (75 Minutes Away):
About Florence: Through the Middle Ages Florence was a fierce competitor to Siena and even to this day they compete for tourists. Each of the cities has its selling points as Florence is a booming Renaissance metropolis filled with fantastic works of art, while Siena feels like its smaller little brother a frozen a bit further back in Medieval times.
We love visiting Florence as a day trip from Siena to see the contrast between the two cities which will help you love Tuscany even more. While Siena never modernized after plagues and famine that crushed the population in the late-1300s, Florence came back strong thanks to its river access and military might to rule the Renaissance. On a day trip from Siena to Florence, you can see work by some of Europe’s best master sculptors, climb the most impressive cathedral dome in Italy, stroll the Arno river, sample Florentine cuisine, and take in one of Europes best sunsets.
Getting Here: It will take you about 1 hour to drive, 1 hour and 15 minutes by express bus, or 1.5-2 hours by train. The express buses run from early in the morning until late into the evening and are much closer to Siena’s city center than the train station which makes it the best option. Rating As A Day Trip From Siena: 10 out of 10.
Read More: Our Florence Travel Guide.
2. San Gimignano (1 Hour Away):
About San Gimignano: The tightly packed hilltop wonder of San Gimignano gives you a great peek into what cities like Florence or looked like before the Renaissance and unified building codes. The compact village of San Gimignano was once overflowing with Medieval skyscrapers and still has 15 of its original 72 tower house very well preserved. These tower houses were used by local affluent families not just for defense, but also as a competitive show of wealth. The magic of this rural village makes it our favorite Tuscan hill town and by far one of the best side trips from Siena.
Getting Here: 50 minutes by car, 65 by Bus 130; in off times you can go to Poggibonsi by bus 131, 136 or by train and check bus 130 for the last leg which will take between 60-85 total minutes. Rating As A Day Trip From Siena: 9.5 out of 10.
3. Chianti Wineries & Castles:
About Chianti: When you dream of wine country in Italy it is probably filled with images of the Chianti region even if you didn’t know it. The premier area of land stretches from Siena to Florence and has many of Italy’s most famous wineries and a number of great castles you can visit. Most of the castles themselves are the wineries, making it a two-for-one visit you won’t forget especially if you rent a car.
The famous wine from Chianti never really sat well with our taste buds, until we finally had it fresh at the source. It is so much more of a bold, multi-flavor wine when you get it locally compared to the dusty nobility version you often find in America. Maybe part of the allure is the mesmerizing views of the rolling Tuscan hills or the slow pace lifestyle, but a day trip from Siena to Chianti.
Getting Here By Bus: Without a car you either have to pay for a pretty expensive small group tour or take the bus. Routes on bus 125 & 127 can get you to some of the key sites within an hour or with transfers all the way to Geve, but you will be missing out on a lot compared to renting a car. Getting Here By Car: Doing a loop by car is 100% the way to go. You can go to Castello di Brolio, then Castello Meleto, Badia a Coltibuono, Radda in Chianti and back to Siena for a total of three amazing castle wineries and a village easily in one day. Rating As A Day Trip From Siena: 9 out of 10 (5 out of 10 if you don’t rent a car).
4. Agriturismo Cooking Classes:
About Agriturismo Cooking Classes: Even as a very novice chef, attending a cooking class at an authentic Agriturismo can turn your vacation into a trip of a lifetime. You can forget everything you know from Olive Garden, and dive right into what real Italian hospitality feels like. An Agriturismo is a little different as they are working country farms which will help you have a real traditional experience.
They are tons of options from light cooking of basic desserts while drinking wine and others where you are preparing an entire dinner. The experience will really help give you a rooted connection to Tuscany as you laugh, cook, drink, and possibly even sing a bit. Taking a day trip from Siena to do a cooking class really is the Romanized version of Tuscany, but in real life.
Getting Here: Varies as some places keep you up in Siena and other places you have to drive to. Rating As A Day Trip From Siena: 9 out of 10.
5. Volterra (60-75 Minutes Away):
About Volterra: Going back to Etruscan times, quaint Volterra was actually a powerhouse thanks to its rich sources.
Getting Here: It will take you about 1 hour to drive, 1 hour and 15 minutes by express bus, or 1.5-2 hours by train. The express buses run late into the evening and are much closer than the train station which makes it a great option. Rating As A Day Trip From Siena: 8 out of 10.
6. Montepulciano (60-75 Minutes Away):
About Montepulciano: Amazing wine town South of Siena accessible by both car and bus without a tour group.
Getting Here: It will take you about 1 hour to drive, 1 hour and 15 minutes by express bus, or 1.5-2 hours by train. The express buses run late into the evening and are much closer than the train station which makes it a great option. Rating As A Side Excursion From Siena: 7.5 out of 10.
7. Assisi (2 Hours Away):
About Assisi: As one of the jewels of the Umbria region, Assisi is home to medieval lanes and a complex dedicated to Saint Francis who was born here. Saint Francis founded the Franciscan order of monks here in 1208 and pilgrim tourism is the main draw to visiting Assisi. One of Saint Francis’ early followers was local Saint Clare who went on to found the convent of Poor Clares which grew to have branches all through Medieval Europe.
Getting Here: 1.5-2 hours by car; but 3-3.5 hours by train with 2 transfers. Rating As A Side Trip From Siena: 6.5 out of 10 (8 out of 10 if you are very religious).
8. Arezzo, Italy (1 Hour Away):
About Arezzo: This little village to the East of Siena can be extremely sleepy, but it bursts to life multiple times a year with amazing Medieval festivals. These festivals center on the main square in town which is one of the most beautiful in Tuscany. Overall we would much rather add a day elsewhere in our trip than visit Arezzo, however, during its many festivals is one of the best day trips from Siena.
Getting Here: It will take you about 1 hour to drive, 1 hour and 15 minutes by express bus, or 1.5-2 hours by train. The express buses run late into the evening and are much closer than the train station which makes it a great option. Rating As A Day Trip From Siena: 6 out of 10 (8 out of ten during festivals).
9. Castello di Celsa (30 Minutes Away):
About Castello di Celsa: In the countryside West of Siena is the vine-covered Castello di Celsa which looks straight out of a movie. While the inside of the castle is closed to the public you are able to visit the grounds and tour the fabulous gardens. Because it is so quick to get to the castle from Siena by bus or car it should be on your radar.
Getting Here: 30 minutes by car; 30 minutes by Bus 37. Rating As A Day Trip From Siena: 6 out of 10.
10. Abbey of San Galgano (50-75 Minutes Away):
About The Abbey of San Galgano: The main chapel was built on the site where the noble knight Galgano Guidotti retired and live as a hermit until his death in 1181. Completed four years after his death, what remains of the abbey today is the open-air shell of the former chapel and a famous sword in a stone said to be Galgano’s. Along with gothic vaulted cellars, you can find mummified hands of thieves that tried to take the sword from the stone.
Getting Here: 50 minutes by car; 75 minutes by bus with 1 change in Rosia (S33 > 122). Rating As A Day Trip From Siena: 5.5 out of 10.
11. Monteriggioni (25 Minutes Away):
About Monteriggioni: As you approach Sienna chances are you’ve seen the hilltop fort of Monteriggioni and asked: “hey what’s that?”. This very tiny village has an intact medieval wall built 1203 with 14 watchtowers to protect Siena along the Medieval road from Florence. While very small it is worth 30 minutes of your time to stop and check it out if you driving by anyway. Monteriggioni is surrounded by vineyards and is famous being used by Dante as a simile for the abyss in his novel Inferno.
Getting Here: 25 minutes by car; 38 minutes by buses 130, 131, or 136 from Siena. Rating As A Day Trip From Siena: 4 out of 10 (best if you are already driving by).