The best San Gimignano day trip from Florence starts early. You walk the town before the tour buses fill its squares, lunch at a winery facing the towers, and spend the afternoon in Certaldo Alto, a quiet brick town reached by funicular. Our tour does it all in seven hours, door to door, with lunch and three wines included.
| The day at a glance | |
|---|---|
| Distance | 56 km from Florence, a little over an hour by road |
| Morning | San Gimignano, before the day-trip buses |
| Lunch | An organic, family-run winery facing the towers: starter and first course with 3 wines |
| Afternoon | Certaldo Alto, the walled upper town, by funicular |
| Length | 7 hours, pick-up and drop-off included |
| Group | Up to 8 guests, private or semi-private |
| Walking | Easy and at your own pace, on cobbled, sloping streets |
| Not included | Museum and tower tickets, gratuities |
Why is San Gimignano worth a day from Florence?
San Gimignano still has the skyline that put it on every Tuscany postcard. In the 12th and 13th centuries its rival families built 72 stone tower-houses, and 14 of them still stand above the walls.
The tallest is the Torre Grossa, 54 m, built around 1310 next to the Palazzo Comunale. The historic centre has been a UNESCO World Heritage Site since 1990.
It’s also a wine town. The hills around the walls make Vernaccia di San Gimignano, the white wine that in 1966 became the first in Italy to get a DOC.
The problem is that everybody knows all this. San Gimignano is one of the most visited towns in Tuscany, and a badly timed visit means queuing behind tour groups on the main street.
What time should you get to San Gimignano?
Before 9:30 in the morning, or after 5 pm. From April to October, and above all in July and August, Piazza della Cisterna is full by mid-morning, once the day-trip coaches have unloaded at the car parks outside the walls.
So on our San Gimignano and Certaldo tour we leave Florence in the morning and do San Gimignano first. You get the two main squares with room to stand still and look up. Then we drive out to lunch while the town is at its busiest.
In winter the crowds thin out, though the morning is still the quietest and most photogenic part of the day.
What should you see in San Gimignano in one morning?
Two to three hours are enough if you go straight to the good parts:
- Piazza della Cisterna, named after the stone well in its centre;
- Piazza del Duomo, right next to it, with the Collegiata and the Palazzo Comunale;
- the Torre Grossa, if you want the view from the top. Tower and museum tickets are paid separately and are not part of our tour;
- the side lanes off the main street, where the crowd thins out within a few steps;
- saffron, the town’s other crop, sold in small jars in the shops.
The guide stays with you the whole morning, and the pace is yours.
Where do you have lunch at a winery near San Gimignano?
On our tour, lunch is at an organic, family-run estate in the hills outside town, with the towers on the other side of the vineyard. It takes guests by appointment only, which is why it stays calm while San Gimignano fills up.
You get a farm-to-table starter and a first course, paired with three of the estate’s wines and a taste of its extra virgin olive oil. Which three wines are poured depends on the estate and the season.
If you have dietary requirements, tell us when you book and the kitchen will plan around them.
Why one winery and not three?
Many San Gimignano wine tours from Florence last about eight hours and fit two or three wineries around a short stop in town. For San Gimignano we think that’s the wrong balance. The town needs time, and one long lunch at a table with three wines tells you more about a place than three quick tastings at a counter.
If wine is the whole point of your day, go to Chianti Classico instead. It starts less than an hour south of Florence, and our half-day tour there fits two family estates, about ten wines and lunch into five hours. We compare that day with our full walking day in half-day or full-day Chianti wine tour.
What is Vernaccia di San Gimignano?
Vernaccia di San Gimignano is the white wine of the hills around the town, made from at least 90% Vernaccia grapes. It was the first Italian wine to receive a DOC, in 1966, and it has been a DOCG since 1993.
In the glass it’s dry and fresh, with crisp acidity and a slightly bitter finish, which is what makes it so good at the table. The Riserva ages for at least 12 months, 4 of them in bottle, and turns more golden.
The paper trail is long. The town’s records mention Vernaccia in 1276, and Dante puts Pope Martin IV among the gluttons of Purgatory for his Lake Bolsena eels drowned in it.
Why add Certaldo to a San Gimignano day trip?
After San Gimignano you’ll want somewhere quiet. Certaldo Alto is the walled, red-brick upper town of Certaldo, on a hilltop in the same Val d’Elsa, and most people on a day trip from Florence never go there.
Giovanni Boccaccio, author of the Decameron, spent his last years in Certaldo and is buried here. His red-brick house still stands in the upper town. A few steps away, the Palazzo Pretorio, where Florence’s governors lived, has a façade covered in ceramic coats of arms.
You go up from the lower town by funicular. The track is 130 m long, a car leaves every 15 minutes from 7:30 in the morning, and the bottom station is about 200 m from Certaldo railway station.
Can you do a San Gimignano day trip from Florence without a car?
You can reach San Gimignano by public transport, slowly. The town has no railway station.
From Florence you take bus 131 to Poggibonsi, or a regional train to Poggibonsi-San Gimignano, then bus 130 up the hill, about 25 to 30 minutes. Allow an hour and a half to two hours each way.
Certaldo is easier: a direct train from Florence takes about 50 minutes, and the funicular is a short walk from the station.
Both towns and a winery in one day, by bus and train, won’t work. Connections change with the season, and the best small estates sit on country roads that no bus reaches.
If you drive, it’s 56 km on the Florence-Siena expressway, with no motorway tolls on that route. You park outside the walls, because the historic centre is a restricted traffic zone, and whoever drives skips the wine. Our guide on whether you need a car in Tuscany goes through the trade-offs.
Private or semi-private?
The tour runs in both formats.
- Semi-private: you share the van with up to 8 travellers, meet at Piazza de’ Mozzi in Florence and follow the standard San Gimignano and Certaldo itinerary.
- Private: we collect you at your hotel or B&B in Florence, and the timing, pace and stops are yours. We can add Siena, or swap San Gimignano or Certaldo for Volterra, the Etruscan town known for its alabaster workshops.
For families, private is the easier choice, because the day can follow the children. Our honest comparison of private, semi-private and group tours goes through the differences.
When is the best time of year for this day trip?
Spring and autumn are the easiest seasons: mild days and fewer people than in summer. In July and August the early start matters most, for the heat as well as the crowds. Our month-by-month guide on when to visit Tuscany has the weather for each month.
From April to October, book at least two weeks ahead. The winery hosts guests by appointment only, and booking early secures both the lunch and the quietest time slot in San Gimignano.
What else pairs well with San Gimignano?
If you have more than one day out of Florence:
- Siena is 75 km from Florence and often combined with San Gimignano, though together they make a long day;
- Volterra, about 30 km from San Gimignano, sees far fewer visitors and fits on a private day;
- Chianti Classico is the natural wine day of the same trip.
San Gimignano is one of the day-3 options in our three-day Tuscany itinerary, and San Gimignano with Certaldo is day 4 of the seven-day itinerary from Florence and Siena. Our guide to the best day trips from Florence compares it with the others.
If you want several of these days in a row, we build them into a tailor-made Tuscany itinerary.
We never take commissions from the wineries we visit, so the estate is chosen for what is in the glass.
FAQ
San Gimignano is 56 km south-west of Florence, a little over an hour by road on the Florence-Siena expressway. The town has no railway station, so by public transport you change at Poggibonsi and take bus 130 up the hill. Allow an hour and a half to two hours each way.
Easily, if someone else drives. Our San Gimignano and Certaldo tour lasts seven hours with pick-up and drop-off: San Gimignano in the morning, lunch at an organic family-run winery facing the towers, with a starter, a first course and three wines, then Certaldo Alto in the afternoon.
Arrive before 9:30 or after 5 pm. From April to October, and above all in July and August, the main squares fill up by mid-morning when the day-trip coaches arrive. Seeing the town first thing, then leaving for lunch at a winery outside the walls, keeps you away from the busiest hours.
Vernaccia di San Gimignano, a dry white wine made from at least 90% Vernaccia grapes, with crisp acidity and a slightly bitter finish. It was the first Italian wine to receive a DOC, in 1966, and has been a DOCG since 1993. The town’s records mention it as early as 1276.
For most travellers it is the quiet half of the day. Certaldo Alto is a walled medieval town of red brick in the same valley, where Giovanni Boccaccio spent his last years. Most day-trippers from Florence never go there, so you can walk its lanes and see the Palazzo Pretorio without queues.
By funicular from the lower town. The line is 130 m long, runs a car every 15 minutes from 7:30 in the morning, and starts about 200 m from Certaldo railway station. Trains from Florence take about 50 minutes, so Certaldo is the easier of the two towns to reach without a car.
Children from 5 years old can join. The walking is easy and at your own pace, with no hiking, but both towns sit on hilltops with cobbled, sloping streets, so comfortable shoes help. On a private tour the timing and stops follow the family. The tour is not wheelchair accessible.
On a private tour you can. We can add Siena to the day, or swap San Gimignano or Certaldo for Volterra, the Etruscan town known for its alabaster workshops. The semi-private tour follows the standard San Gimignano and Certaldo itinerary and meets at Piazza de’ Mozzi in Florence.
