Siena and San Gimignano are the two towns every Tuscany itinerary includes, usually on the same day and usually from Florence. They are worth it. Siena is a complete medieval city that lost its rivalry with Florence and therefore never got rebuilt, and San Gimignano is a small hill town that kept a skyline of stone towers when everywhere else lost theirs. The trick with both is the timing, because between about ten and five they belong to the coaches, and either side of that they are extraordinary.
Siena
The Campo is the main square, shell-shaped and sloping, ringed by cafes and closed to traffic, and it is one of the great public spaces in Europe. Sitting on the bricks in the middle of it is what people do.
The cathedral is the set-piece: striped marble inside and out, a floor of inlaid marble panels that are uncovered only for part of the year, and a library off the nave with frescoes in colours that look freshly painted.
The tower on the town hall gives the view over the roofs, involves a great many steps and is worth them.
The old hospital opposite the cathedral is now a museum and is the most underrated thing in the town.
The contrade, the seventeen districts that compete in the Palio, are visible everywhere once you notice the flags and symbols on the streets, and they explain why this town works the way it does.
San Gimignano
The towers are the reason to come: medieval status symbols built by rival families, a number of which survive, giving a small hill town a skyline like nothing else in Italy.
It is small. You can walk it in an hour, which is why it is usually paired with Siena.
The approach is half of it. The view of the towers from the road in is the photograph everybody wants, and it is better than anything from inside the walls.
The main street is commercial, heavily so in the middle of the day, and two turns off it the town goes quiet immediately.
The local white wine is one of the oldest named wines in Italy and is worth ordering here rather than anywhere else.
Doing it in a day
By bus from Florence, with a direct service to Siena and a change for San Gimignano, which is straightforward and cheap.
By car, an easy drive with the option of the back roads through the vineyards, which is much of the appeal.
Park outside the walls in both towns, always, because both have restricted traffic zones enforced by camera and a fine that arrives months later.
Give Siena the larger half of the day, because there is simply more of it.
Do not add a third town. Two hill towns and the drive between them is a full day.
The countryside in between
This is the part that does not appear in the itinerary and is the reason to have your own transport or a good tour.
The road between the two runs through the classic Tuscan landscape of ridges, cypresses and vineyards.
A winery stop fits naturally into the middle of the day, and the region between Florence and Siena is where the best known Tuscan reds come from. Our guide to the Chianti wine road covers the route, the tastings and how to do it without driving badly.
Lunch in a village rather than on a main square in either town is the better meal by a wide margin.
Where this fits in a Tuscany trip
These two towns are the day trip, and the region deserves more than a day trip.
Our guide to Tuscany covers how the region fits together, which parts reward a base and which are drive-through, and how many nights it actually takes.
Back in the city, the two ticketed museums are the other half of a Florence stay, and our guide to the Uffizi and the Accademia covers booking them without a queue or a markup.
The short version
Do both in a day if that is what you have, with San Gimignano first thing before the coaches and Siena for the longer, later half. Park outside the walls in both towns to stay clear of the restricted zones. Give Siena a full afternoon for the Campo, the cathedral, the tower and the old hospital, and give San Gimignano an hour of towers and a glass of the local white. Take the back roads in between and stop for lunch in a village. And if you can spare a night, spend it in Siena.
