Siena is about an hour and a quarter from Florence by coach, and San Gimignano a further change of bus beyond it. Neither town has a useful railway station, so this is the one day trip from Florence where the transport decision shapes everything else.
Done well, it is the best day out in Tuscany: a medieval city built around a shell-shaped square, then a walled hill town of towers with vineyards on every side. Done badly, it is hours of waiting for connections.
Is it worth a day trip?
Siena alone is comfortably worth a day and easy to reach. Adding San Gimignano is worth it with a car or on a tour, and ambitious by public transport, because the two towns are linked only by a change at Poggibonsi and the timetable thins at weekends.
Split them across two days if you are in Florence for a week. Siena repays a slow morning in the cathedral and an afternoon in its contrade, the seventeen districts that still organise city life. San Gimignano is better late, once the coaches have gone.
Skip San Gimignano altogether if the day would leave you forty minutes there. Skip Siena on 2 July and 16 August, the dates of the Palio, unless the race is why you are going: the town is full and the square closed off. Our note on how far is too far for a day trip is worth two minutes before you commit to both towns.
Getting there
To Siena. The coach beats the train. Autolinee Toscane runs the 131R fast service from Florence's bus station beside Santa Maria Novella, roughly seventy-five minutes, setting you down near the centre. The train involves a change at Empoli, takes longer, and leaves you below the old town. Buy bus tickets from Autolinee Toscane, in its app or at the station.
To San Gimignano. There is no railway at all. From Siena you take the 130 bus to Poggibonsi and change for the run up to San Gimignano, around twenty-five minutes. Check return times before leaving Siena: the last useful services back are earlier than you expect and much thinner on Sundays.
By car. Around an hour and a quarter to Siena, with the two towns linked directly, and car parks outside both sets of walls. A car is what makes the plan below relaxed rather than tight.
The day, hour by hour
09:30, Piazza del Campo. Siena's great square slopes like a shell towards the Palazzo Pubblico, paved in brick divided into nine segments for the medieval council that built it. Sit on the paving for ten minutes before doing anything else.
10:15, Palazzo Pubblico. The city hall still functions as one, with the Museo Civico upstairs. Go in for Ambrogio Lorenzetti's Allegory of Good and Bad Government, painted in the 1330s across three walls of the council chamber, and Simone Martini's Maestà next door. Political art, made for the men who had to govern under it.
11:00, Torre del Mangia. One of the tallest medieval towers in Italy, and a narrow, unrelenting climb. Numbers are capped, entry is in timed groups, and tickets are sold on the day at the Palazzo Pubblico ticket office rather than online, so buy yours on arrival. Check it is open before building the day around it.
12:00, Siena Cathedral. Striped black and white marble inside and out, with Nicola Pisano's carved pulpit and the Piccolomini Library off the nave, frescoed by Pinturicchio in colours that look barely aged. The inlaid marble floor is the extraordinary feature, covered for much of the year and uncovered for a set period, usually late summer into autumn. Check the dates on the cathedral's site, along with the Gate of Heaven rooftop walk.
14:30, Piazza della Cisterna. In San Gimignano now. The triangular square is paved in herringbone brick around a thirteenth-century well and ringed by tower houses. Fourteen medieval towers survive from a great many more, and this is where they crowd closest.
15:15, Torre Grossa. The tallest of them, and the only one open to climb, entered through the Palazzo Comunale and its picture gallery. From the top you get the towers below and the Val d'Elsa vineyards running out in every direction.
16:00, gelato on Piazza della Cisterna. The gelateria on the square has won world championships and takes itself seriously, with saffron and Vernaccia among the flavours, both local. Queue, take a cone, sit on the steps by the well.
16:45, Rocca di Montestaffoli. Finish at the ruined fortress above the town, a short walk up through olive trees. The interior is a grassy enclosure you can walk into, and the surviving wall gives the best view of the skyline, the towers stacked against the light.
What to book ahead
Book the Siena cathedral complex and the Gate of Heaven online, as the rooftop slots are small and limited. The Torre del Mangia ticket has to be bought in person on arrival. By bus, check the Poggibonsi connection and the last return to Florence before you set out.
Open this day trip in Tralendr
The day is saved as a ready-made plan, both towns and every stop in order on one map, which makes the distance between them easy to judge. It opens without an account and can be edited: drop San Gimignano, add an hour in Siena, move the times to match your bus.
Open the Siena and San Gimignano day trip plan and share the link with whoever is coming. Our day trip method explains how to build a day backwards from the last departure, which matters more here than on most routes.
If this looks like too much travel, the Pisa day trip from Florence is under an hour each way by train and needs almost no planning. The rest are in our day trip collection.