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Day trips from Siena: Where to go and how to get there
Discover the best day trips from Siena — from medieval towers in San Gimignano to world-class wine in Montalcino. Bus, train, and car options included.
Using Siena as your base opens up some of the best day trips from Siena in all of Tuscany — San Gimignano, Montalcino, and Florence are just a few of the world-famous destinations within easy reach.
Siena is ideally located, so most places in the region can be reached by bus or train. Even if your wishlist includes areas off the beaten track, there are car hire options and tour guides who specialize in the region’s hidden gems. The city itself is also worth building time around. If your visit falls in July or August, the Palio di Siena is not something you’ll want to miss.
Below, we cover eight of the best day trips from Siena to make your trip a memorable one. And if you want to explore the country further, then you should check out our Italy travel guide.
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Best day trips from Siena
Hiring a car will give you the most flexibility when planning day trips from Siena, but there are plenty of options available for those of you who don’t fancy driving being part of your holiday.
Regular bus services, trains, and guided tours provide options to see almost all of Tuscany. However, it would be almost impossible to fit all the wonders of this region into one lifetime, nevermind one trip.
| Destination | Distance from Siena | Travel Time | Best Transport |
|---|---|---|---|
| San Gimignano | 42km | 1 hour | Bus |
| Monteriggioni | 15km | 20 minutes | Bus or Car |
| Montalcino | 45km | 1 hour | Car or Bus |
| Pienza & Val d’Orcia | 55km | 1 hour 15 mins | Car |
| Montepulciano | 65km | 1 hour 20 mins | Train |
| Florence | 75km | 1 hour 15 mins | Train |
| Crete Senesi | 20-40km | 30-45 mins | Car |
| Chianti | 30-60km | 45 mins-1.5 hours | Car |
San Gimignano
Best for medieval towers and artisan shopping
San Gimignano’s medieval skyline rises dramatically above the surrounding countryside, so it’s easy to see how the town earned its nickname, the “Town of Fine Towers.“
The panoramic view from the top of Torre Grossa is the highlight for most visitors, but the cobbled streets and artisan shops at ground level are just as rewarding.
How to get there: There is no direct train from Siena to San Gimignano. Buses run several times daily from Siena’s train station, with a journey time of around one hour. Tickets cost approximately €7.
Monteriggioni
Best for a quick medieval escape
Monteriggioni’s perfectly preserved stone walls and watchtowers are among Tuscany’s most striking sights, and unlike many of the region’s most visited spots, they feel genuinely unspoiled.
It is a quieter destination, making it better suited to a half-day than a full one. That said, we’d recommend building in time for a long, leisurely lunch in the main piazza.
How to get there: Autolinee Toscane’s line 131 bus runs directly from Siena to Monteriggioni in around 22 minutes and costs €1–3.
Montalcino
Best for world-class wine and rolling vineyard views
Montalcino is the home of Brunello di Montalcino, one of Italy’s most celebrated wines. Set among rolling vineyards in the southern Val d’Orcia, the town combines beautiful scenery with exceptional food and drink.
It works particularly well as an evening visit, there are several local wineries and nearby castles offer tastings in atmospheric surroundings.
How to get there: Autolinee Toscane’s 112 and 114 bus services run from Siena through the Tuscan countryside, stopping close to the town centre. The journey takes just over an hour.
Pienza and the Val d’Orcia
Best for Renaissance towns and postcard-perfect landscapes
When people picture an ideally designed Renaissance town, they’re probably picturing something like Pienza. Commissioned in the 15th century by Pope Pius II and now a UNESCO World Heritage Site, it’s best known for its local pecorino cheese, but the architecture and views are equally worth the trip.
Start with a cappuccino and a walk around the town centre in the morning, then head out into the Val d’Orcia in the afternoon. This UNESCO-listed valley is everything the postcards promise: rolling hills, cypress-lined roads, and golden fields stretching to the horizon. A car is the best way to take it all in.
How to get there: Autolinee Toscane buses from Siena to Pienza typically change in Buonconvento and take 1.5 to 2 hours. Hiring a car is the more practical option if you want to combine both Pienza and the Val d’Orcia in one day.
Montepulciano
Best for noble wine and sweeping hilltop views
If you’ve enjoyed Montepulciano wine at home, tasting it at the source is a different experience entirely. Vino Nobile di Montepulciano is one of Tuscany’s finest reds, and the hilltop town that produces it is equally impressive.
Lunch on the Piazza Grande — the highest point in the town, with panoramic views across the valley is one of the better ways to spend an afternoon in Tuscany.
How to get there: Direct Trenitalia Regionale trains run daily from Siena to Montepulciano, with the journey taking just over an hour. Tickets are usually inexpensive, making it one of the easier day trips to plan.
Florence
Best for world-class art, architecture, and history
Florence is essential for anyone visiting Tuscany, particularly on a first trip to the region. The Duomo, the Ponte Vecchio, and the Uffizi Gallery are world-famous for a reason, and all are within easy walking distance of each other.
Florence rewards a full day’s visit — arrive early to make the most of it and to beat the queues at major attractions. If you’re thinking of extending your stay and using Florence as a base, our guide to day trips from Florence covers even more of the region.
How to get there: Trenitalia’s regional (Regionale) trains run regularly from Siena to Florence Santa Maria Novella, with a journey time of around 1 hour 15 minutes. This is one of the easiest day trips from Siena without a car.
Crete Senesi
Best for dramatic, crowd-free Tuscan scenery
Crete Senesi is often overshadowed by the Val d’Orcia, but it is every bit as beautiful and significantly less visited. Characterised by distinctive clay hills and wide-open landscapes, it offers some of the most photogenic scenery in Tuscany.
The village of Asciano is one of the area’s quiet highlights, with a local museum and some excellent restaurants.
How to get there: A car is the best option, as many viewpoints and villages are difficult to reach by public transport. The area begins around 20–40 km from Siena.
Chianti
Best for wine routes, scenic villages, and leisurely drives
Chianti means wine to most people, but the region offers far more than its famous bottles. Charming villages, some of Italy’s most scenic country roads, and a genuinely relaxed atmosphere make it one of the most enjoyable parts of Tuscany to explore.
Greve in Chianti, Castellina in Chianti, and Radda in Chianti are all worth stopping in for wine tasting, local food, and a slower pace.
How to get there: A car makes exploring Chianti significantly easier, especially for visiting wineries or smaller villages. For those relying on public transport, Autolinee Toscane’s 125 bus line connects Siena to Castellina in Chianti and Radda in Chianti.
Tips for planning day trips from Siena
A little planning makes a big difference, especially during the busy summer season.
- Book trains in advance. Popular routes like Siena to Florence can sell out quickly in peak season. Book through Trenitalia or a reliable booking platform.
- Check ZTL zones before driving into town centres. Many Tuscan towns restrict access for non-resident vehicles, and fines are common.
- Avoid midday departures in summer. Early mornings and late afternoons are far more comfortable in exposed areas like the Val d’Orcia and Crete Senesi. Rural Tuscan roads are often narrow and winding, so journeys typically take longer than they look on a map, so leave extra time.
- Pack for the conditions. Hilltop towns like Pienza and Montalcino involve a lot of uphill walking on stone streets with limited shade. Bring water, sunscreen, and comfortable shoes.
- Check Sunday and public holiday timetables. Both train and bus services are often reduced outside weekdays.
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