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Most San Gimignano romantic experiences are small and close together. There's a 700-year-old fresco of a newly married couple in the town hall. There's gelato made with local saffron, a glass of Vernaccia in the old fortress garden and the view from Torre Grossa. You can cover all of them in a couple of hours. The best part is having time to enjoy them without anyone rushing you along. That's why we build them into a private day from Florence, with a vineyard lunch and an afternoon in Siena.
The Room with the Bathtub
Inside the Palazzo Comunale, climb the stone staircase from the courtyard. At the top there's a small room that once belonged to the podestà, the outsider the town brought in to govern it. Some time in the early 1300s, a painter called Memmo di Filippuccio covered its walls with scenes of a young couple's married life. In one panel the two of them sit together in a wooden tub. In the next, the wife climbs into bed beside her husband while the curtain is pulled back.
They were almost certainly meant as moral instruction about youth and marriage, and art historians still disagree on exactly which text they illustrate. Seen without the footnotes, they look a lot like a honeymoon.
Medieval painting rarely shows ordinary affection instead of saints. This room does, and it's easy to walk past. The rest of the museum is full of altarpieces. There's also the frescoed council hall where Dante spoke as Florence's ambassador in 1300.
The same building is the way up Torre Grossa, the tallest of the 14 surviving towers. It's just over 200 steps, and the last stretch feels more like a ladder. From the top you see the whole Val d'Elsa. You don't see much of San Gimignano's skyline, though. You're standing on the biggest piece of it.
San Gimignano Romantic Experiences on a Private Tour
On our private tour to Siena and San Gimignano, the guide tells the town's story on the drive out of Florence. You hear about the families who raised 72 towers to outdo each other, and about the pilgrims on the Via Francigena. Then came the plague of 1348 and a long decline. The town lost its trade and its independence, and it simply stopped rebuilding.
When you arrive, you already know what you're looking at. Then the time in San Gimignano is yours, without anyone at your elbow.
That suits a couple. You can spend forty minutes in the podestà's room or skip the museums entirely and sit on a wall. You also get handy maps of the places you visit. Ask the guide before you set off if you want to know which gate to head for. Pick-up and drop-off are at your accomodation in Florence. You travel in an air-conditioned minivan with just the two of you on board. There's no meeting point to find in the morning and no group to wait for at the end of the day.
Gelato on the Cistern Steps
Piazza della Cisterna is the busiest square in town. Around midday it isn't very romantic at all. Gelateria Dondoli has been on the square since 1992. Sergio Dondoli has won the Gelato World Championship more than once, so the queue is long for good reasons.
The flavour with the strongest local link is Crema di Santa Fina, with San Gimignano saffron and pine nuts. Saffron helped make the town rich in the Middle Ages, long before the tourists came. Sit on the steps of the old well if there's room. Or walk your cups down Via San Matteo toward the northern gate. That street empties out much faster than Via San Giovanni.
Is There a Quiet Spot at the Top of Town?
There is. Behind the Collegiata, a short lane climbs to the Rocca di Montestaffoli. The Florentines built this fortress once San Gimignano came under their control. Today only the walls remain. Inside them you'll find a small garden of olive trees and a stubby tower with the classic view of the skyline. It's the highest point in town. In the early afternoon or toward closing time, it's often quieter than the squares below.
Next door, the local wine consortium runs the Vernaccia di San Gimignano Wine Experience in the Villa della Rocca. It has a tasting counter for the town's white wine. A glass on the terrace, above the vineyards it came from, is an easy way to spend half an hour. Curious about what's in the glass? Our piece on Vernaccia wine of San Gimignano explained covers it properly.
Something Small to Take Home
San Gimignano is not a cheap place to shop for souvenirs. Plenty of what you see on the main street comes from somewhere else. A few workshops are different: hand-painted ceramics, saffron in small jars, leather from family workshops. Do you want one thing together that will still mean something in ten years? Have a look at our notes on San Gimignano local crafts before you go.
Lunch with the Towers on the Horizon
When the free time is up, the minivan takes you into the Chianti hills. You stop at a family-run organic farm and winery, with a view back to the hilltop town you've just left. First there's a short tour of the farm, the cellar and the vineyard rows. Then you sit down to homemade Tuscan food and a tasting of four wines. The farm can prepare gluten-free or vegetarian dishes if you tell us in advance.
It's an informal tasting, not a sommelier lecture. The people at the table are the family who work the land. Ask about the olive harvest if you're there in late autumn. Pressing starts around the end of October in this part of Tuscany. The new oil is bright green and peppery, and it's one of the better reasons to travel in November.
Siena in the Late Afternoon
Siena comes last. Your guide walks you through it properly, with the stories of the Palio and the 17 contrade that compete for it. Then you go into the Duomo, and the ticket is part of the tour. Look down at the inlaid marble floors and up at the painted ceiling of the Piccolomini Library. If a service closes the cathedral, you visit the Santa Maria della Scala museum instead.
After that, you have free time in Piazza del Campo. The square slopes like a shell, and late in the day people sit straight on the warm brick. If you have the legs for it, the Torre del Mangia gives the best view in the city. Still unsure whether a day really needs both towns? Our comparison of Siena vs San Gimignano shows how different they feel.
Before You Book
The whole day lasts around ten hours. Both towns have steep streets and uneven paving, so wear proper walking shoes. The tour isn't suitable for anyone with limited mobility or for wheelchair users. You can cancel for free up to 24 hours before departure. You can also change the date on the same terms, depending on availability.
None of the San Gimignano romantic experiences above need much planning on your side. The frescoes, the tower, the gelato and the Rocca garden all sit within a few minutes' walk of each other. The private tour takes care of everything in between. That means the drive, the parking below the walls and reaching Siena in time for the cathedral.
