Everyone does Florence and then wonders what else Tuscany has. The answer, for most people with a spare day, is Siena and San Gimignano — and the honest version is that one of them is a proper city you could spend two days in and the other is a very beautiful village you’ll be finished with in three hours.
Knowing which is which before you go makes the day work much better.
Siena is the substantial one
Siena was Florence’s great rival for centuries until plague and politics settled the argument. What’s left is a medieval city centre that barely changed afterwards, which is exactly why it’s so remarkable now.
The centre is a UNESCO site, entirely walkable, and steep. Genuinely steep — it’s built across three hills and you’ll feel it. Comfortable shoes are not a suggestion here.
Give it four hours minimum. Six is better.
One structural thing worth knowing before you arrive: Siena is divided into 17 contrade, each with its own flag, colours, church, fountain and fierce identity, and you’ll see those flags hanging over the streets everywhere. They aren’t decoration for tourists. People are baptised into a contrada and stay in it for life, and half of what looks like charming medieval pageantry is a living civic structure that still organises real social life.
Piazza del Campo and the Palio
The Campo is a shell-shaped square that slopes down towards the town hall, and it’s one of the great public spaces in Europe. People sit on the brick and just… stay there. You will too.
Twice a year, on July 2 and August 16, they cover it in dirt and run a bareback horse race around the edge — the Palio. It lasts about 90 seconds, it’s ferociously contested between the city’s 17 contrade (districts), and the whole city organises its year around it.
Going for the Palio is a completely different trip from going any other day. The centre is packed, accommodation triples in price, and standing in the middle of the Campo is free but means arriving hours early and not leaving. Worth doing once if that appeals.
The Torre del Mangia, the tower on the Campo, is 400 steps and gives you the best view in Tuscany. Timed tickets, book ahead in summer.
The cathedral is the one to pay for
Siena Cathedral is black-and-white striped marble inside and out and it is genuinely astonishing. Better, I’d argue, than Florence’s — smaller but far more overwhelming.
The floor is 56 inlaid marble panels made over 200 years, and here’s the thing: they’re covered for most of the year to protect them. They’re uncovered for roughly seven weeks, usually late June to late July and again from mid-August to mid-October. If you’re there then, it’s a completely different experience.
The Piccolomini Library off the nave has frescoes so bright they look freshly painted. Most people walk past the door. Don’t.
San Gimignano is a beautiful three hours
Fourteen medieval towers on a hill, visible from miles away, looking like a small Manhattan built in 1300. There were 72 of them once — wealthy families competed by building higher, which is a very human way to run a town.
It’s stunning and it’s tiny. You can walk the whole thing in 40 minutes. The main street runs from one gate to the other and it’s lined with shops selling saffron, wine and leather.
Be honest with yourself: it’s very touristy. Between about 10am and 5pm in summer the main street is a slow-moving crowd. Arrive before 9:30 or after 5 and it transforms into somewhere magical.
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What to actually do there
Climb the Torre Grossa, the only tower open to the public, for the view over the Tuscan hills.
Try the Vernaccia, the local white wine and Italy’s first ever DOC. It’s genuinely good and unlike most Tuscan wine it isn’t red.
Eat gelato at Gelateria Dondoli on Piazza della Cisterna, which has won world championships and has a queue to prove it. Yes it’s a tourist thing. It’s also excellent.
Look at the frescoes in the Collegiata. Fourteenth-century, floor to ceiling, and far less busy than the street outside.
If you’ve got an extra half hour, walk out to the far end of town past the fortress. The crowd thins to almost nothing within about 200 metres of the main street, the view opens out over the Val d’Elsa, and you get a version of San Gimignano that actually feels like the hill town it is rather than a very pretty shopping street.
Doing both in one day
It works, but it’s tight. Suggested shape:
- 8:00am — leave Florence.
- 9:15am — San Gimignano, before the crowds. Two and a half hours.
- 12:00pm — drive to Siena, about an hour.
- 1:00pm — lunch in Siena.
- 2:00pm — cathedral, Campo, tower, wander.
- 6:30pm — back to Florence.
Do San Gimignano first. It’s the one that gets ruined by crowds, and Siena is big enough to absorb them.
Getting there
By car is easiest and lets you do both. Note that both towns have ZTL restricted zones — driving into the centre without a permit means an automatic fine that arrives at your house months later. Park in the designated car parks outside the walls.
By bus, Siena is straightforward: about 75 minutes direct from Florence’s main bus station. San Gimignano needs a change at Poggibonsi and takes about 90 minutes.
By train, don’t bother for Siena — the station is well below the old town and the connection is slower than the bus. San Gimignano has no station at all.
By organised tour is genuinely reasonable here if you don’t want to drive. Most combine both plus a winery, and they handle the ZTL problem for you.
FAQ
If I only have time for one, which? Siena. It’s a real city with more to see and it holds up for a full day. San Gimignano is a beautiful stop, not a destination.
Is a car necessary? No, but it makes combining them much easier and lets you stop in the countryside between, which is half the point of Tuscany.
Best time of year? May, June, September, October. August is hot and packed. Winter is quiet and lovely but some things close.
How much does it cost? Siena Cathedral around €16 with the library, Torre del Mangia around €10, Torre Grossa in San Gimignano around €9. Budget €50 per person for the day including lunch and entries.
Should I add Pisa? Only if you specifically want the tower photo. Three towns in a day means seeing none of them properly.
