I know everyone talks about Florence when it comes to Tuscany, but Siena was a very pleasant surprise.
We visited Siena during a winter road trip through Tuscany and spent two nights here, arriving by car and staying just outside the historic centre. That slower pace on the outskirts completely changed how the city felt.
We were still close enough to walk everywhere, but if we wanted to ditch the crowds and day-trippers, it was easy.
Visiting Siena in winter meant fewer crowds, no rushing between sights, and staying overnight made a huge difference. Early mornings were peaceful, viewpoints were empty, and walking the medieval streets felt relaxed instead of overwhelming.
I remember visiting the cathedral early one morning to take some photos of the outside and thinking it would be busy at 8 am, but when I arrived there was one other person there.
We had time to wander, stop for coffee, and take in details that are easy to miss during busier months.
That said, I know not everyone can visit in the off-season. So I’ve done all the planning for you in this guide, which covers the top sights, how to get to Siena, and everything you need to know to make the most of your trip, no matter what time of year you visit.
Disclaimer: Please note that some of the links in this article may be affiliate links. This means that, at no extra cost to you, I may earn a small commission if you click on or make a purchase through these links.
⏰ Short on time?
Our Picks for Hotels with Views in Siena
($$) NH Siena – Where we stayed
($$$) Hotel Athena
($$$) Hotel Palazzo Ravizza
👉 View more hotels in Siena here
Things to do in Siena
– Horseback Riding Tour in the Tuscany Countryside
– Siena Cathedral
– Siena Walking Tour with a Local
– Wine tasting Experience with Tuscan Sparkling Wines
Short on time? Take a day trip to Siena from Florence
How to Get to Siena
We arrived by car and found this to be one of the easiest ways to visit Siena, especially in winter. The historic centre is pedestrian-only, but there are several car parks just outside the old city walls.
Staying near the centre meant we could park once and walk everywhere. This made arrival and departure far less stressful than juggling luggage on public transport.
Siena doesn’t have a direct high-speed train station. Most travellers arrive via Florence and then transfer to a regional train. The journey from Florence takes about 1.5 hours and is scenic, but slower.
Buses from Florence and other Tuscan towns are often quicker than trains and arrive closer to the historic centre.
Where to Stay in Siena
We stayed at NH Siena, just outside the historic centre, and it was a great base for exploring the city.
Staying here gave us:
- Easy car access and parking
- A short walk into the old town
- Quiet evenings away from day-trip crowds
If you want convenience without staying deep inside the ZTL zone, this is a solid option.
👉 Check availability at NH Siena here
If you prefer staying inside the walls, look for hotels near Piazza del Campo or Santa Maria della Scala so you can explore early and late, when Siena feels most atmospheric.
Our Picks for Hotels with Views in Siena
($$) NH Siena – Where we stayed
($$$) Hotel Athena
($$$) Hotel Palazzo Ravizza
Top Things to Do in Siena
The heart of Siena is Piazza del Campo, a shell-shaped square that feels more like a giant outdoor living room than a traditional piazza.
In winter, it was calm and spacious, with locals passing through and people sitting on the sloped pavement enjoying the light. This is also where the famous Palio horse race takes place twice a year, transforming the square into a packed, high-energy arena.
Just off the square, you’ll find cafés, bakeries, and small side streets worth wandering.
At the upper edge of the piazza sits Fonte Gaia, a decorative fountain that often gets overlooked.
It’s a small detail, but worth stopping at, especially early in the day when the square is quiet. The current fountain is a replica, but it still adds character and history to the space.
👉 Short on time?
Consider taking a walking tour of Siena so you don’t miss anything!
One side of Piazza del Campo is dominated by Palazzo Pubblico, Siena’s historic town hall.
Inside, you’ll find frescoes that tell the story of Siena’s medieval government, including the famous Good and Bad Government cycle. Even if you don’t go inside, the exterior alone is impressive.
Attached to the palace is the Torre del Mangia, one of the tallest medieval towers in Italy. Climbing the tower involves a lot of steps, but the views over Siena and the surrounding Tuscan countryside are worth it on a clear day.
Directly opposite the cathedral is Santa Maria della Scala, a former hospital turned museum complex.
This was once one of Europe’s most important hospitals, serving pilgrims travelling the Via Francigena. Today, it’s a layered museum with frescoed halls, underground spaces, and rotating exhibitions.
It’s large, uncrowded, and easy to explore at your own pace.
The Siena Cathedral is one of the most striking churches in Italy.
The black-and-white marble exterior is unmistakable, and the interior is packed with detail. Highlights include:
- The patterned marble floor
- The Piccolomini Library
- Sculptures by Michelangelo
- Views from the Gate of Heaven rooftop walk
In winter, we could visit without queues. If you’re visiting in summer, tickets should be booked in advance.
Just outside the city centre is Orto de’ Pecci, a peaceful green space with views back toward the old town.
It’s a great place to take a break, especially after exploring museums and churches.
One of my favourite moments in Siena happened early in the morning at Orti de’ Tolomei.
We walked here just after sunrise, and it was completely quiet. From this viewpoint, Siena slowly lights up as the sun comes up behind the city. No crowds, no noise, just rooftops, towers, and soft light.
If you enjoy photography or peaceful mornings, this spot is absolutely worth the walk.
These two sites sit slightly away from the main tourist flow but are well worth visiting.
The Basilica of San Domenico is a large, simple church that holds relics of Saint Catherine. Nearby, the Sanctuary of Santa Caterina is built around her former home and offers a quieter, more reflective experience.
Food to Try in Siena
One thing you must try in Siena is pici pasta.
We had pici during our stay, and it quickly became one of my favourite Tuscan dishes. It’s thick, hand-rolled pasta, usually served with simple sauces like garlic tomato or cacio e pepe-style combinations.
Other local specialties include:
- Ricciarelli almond cookies
- Panforte
- Cured meats made from cinta senese pork
Winter is a great time to enjoy Siena’s food scene, with warm restaurants and less need for reservations.
👉 Make sure to add on a Wine tasting Experience with Tuscan Sparkling Wines
Day Trips from Siena
Siena makes a great base for exploring Tuscany.
Popular day trips include:
- Montepulciano for wine and views
- San Gimignano for its towers
- Pienza and Val d’Orcia landscapes
- Montalcino for Brunello tastings
👉 Read Next: 10 Best Things to Do in Tuscany Italy
Visiting Siena in Winter vs Summer
We visited Siena in winter, and it made a huge difference.
Winter meant:
- Fewer crowds
- No ticket queues
- Calm mornings and evenings
- Easier parking and walking
In summer, Siena is much busier, especially around Palio season. If you’re visiting between late spring and early autumn, you should:
- Pre-book tickets for the cathedral and tower
- Expect crowds in Piazza del Campo
- Book accommodation earlier
Winter isn’t for everyone, but if you prefer quieter travel, it’s one of the best times to visit Siena.
👉 Want to have a unique experience? Try Horseback Riding Tour in the Tuscany Countryside
Frequently Asked Questions About Siena
Yes. Siena offers medieval history, incredible architecture, and a slower pace than larger Tuscan cities.
One full day covers the highlights, but two days allows for a relaxed visit.
Yes, but you must park outside the historic centre.
Spring and autumn are popular, but winter is quieter and less crowded.
Yes. The historic centre is compact but very hilly.
In summer, yes. In winter, it’s often not necessary.
Pici pasta, ricciarelli, panforte, and local cured meats.
Yes. It’s perfectly located for exploring Tuscany.
Read More ✈️
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