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Italy planning guidePlanning a day in Siena and San Gimignano from Florence

Oct 15, 2026, 5 min read, by Exclusive World Tours

This guide is for you if you are staying in Florence and want the two medieval towns to the south in one day. It covers the dates that change everything in Siena, when the cathedral floor is on view, how the ten hours are split, and who in your group might want a different day.

The Palio, and the days around it

Siena's horse race fills the Piazza del Campo on 2 July and 16 August. The race itself is three laps of the square and usually lasts no more than about ninety seconds. Ten of the city's seventeen contrade, its historic districts, ride in each one.

The race is only the end of it. The square is laid with a track of earth, a mix of tuff, clay and sand, and trial races are run on the evening of the horse lottery and twice a day for the two days after. On race day crowds arrive in the morning and the centre of the Campo fills until the police close the entrances.

So if you want Siena as it is on an ordinary day, avoid the few days before each date as well as the dates themselves. If you want to see the Palio, you need a different plan from this one: a day in Siena on race day is about the race, not the towns.

The cathedral floor, and other dates to check

Siena's cathedral has a marble floor of inlaid scenes, and for much of the year it is covered. It is uncovered for some weeks from late June, and again from the second half of August into the autumn. If the floor is a reason you are going, pick a date in those windows. The dates change every year, so check the cathedral's official site.

A few more points from the cathedral's timetable, which is set each year:

  • Sundays and holidays. The cathedral opens only in the afternoon, from 13:30 for most of the year. We reach Siena at 13:45, so a Sunday still works.
  • May. Only the cathedral itself is open that month, not the rest of the complex.
  • Short days. On some days in June and August, closing is earlier, at 18:00.
  • Last entry. Admission stops half an hour before closing, and services can change the hours at short notice.

How the ten hours fit together

You are collected at 07:00 and back in Florence at about 17:00. The order is chosen to beat the crowds:

  • San Gimignano from 08:00. Three and a half hours in the town before the coaches arrive.
  • Lunch at a winery from 11:30. An estate in the hills below the town, with Vernaccia, the local white wine.
  • Siena from 13:45. Two hours for the Campo and the striped marble cathedral at the top of the hill.
  • Home through Chianti from 15:45. The old road north through the vineyards, with a stop in a village if there is light.

San Gimignano has been a UNESCO World Heritage site since 1990. It was a relay point for pilgrims on the Via Francigena, the road to and from Rome. Its families built around 72 tower-houses, and 14 survive. In the town's cathedral and other buildings are frescoes from the fourteenth and fifteenth centuries, including Taddeo di Bartolo's Last Judgement and Ghirlandaio's scenes from the life of Santa Fina. Your morning there is long enough to go inside as well as walk the lanes.

Because the car is yours, the plan can bend. The walled village of Monteriggioni is on the road between the two towns, and adding it takes about forty minutes.

Doing it yourself, or with a driver

One town on its own is a simple outing. Two towns, a winery lunch in the countryside and the Chianti road home are harder to fit together without a car. The order is the main advantage of a private day: San Gimignano while it is quiet, Siena in the afternoon light, and no timetable deciding when you leave. The price depends on the size of your group; see it on the tour page.

What to book and bring

Entrance to Siena cathedral is not included, and nor are lunch or any tastings. Buy the cathedral ticket through its official site, choosing a time that suits a 13:45 arrival, and remember the Sunday afternoon opening.

  • Comfortable shoes. Siena's cathedral sits at the top of the hill, and both towns are walked on foot.
  • Money or a card for lunch and anything you taste at the estate.
  • Water and a hat in summer. Most of the day is spent outdoors.

Who it suits, and who should think twice

It suits a first visit to Tuscany, families who want towns more than wine, and anyone who wants to see the country between Florence and Siena without driving it.

Think twice in these cases:

  • Wine is the main reason for your trip. This day has one winery lunch. Our Chianti wine tour visits two estates and three villages.
  • Your date is 2 July or 16 August. Choose another day for this tour, or plan the day around the race.
  • You want Pisa too. Pisa is in the other direction and makes a different day. Ask us.
  • You are more than 16. Two vehicles travel together on one booking. Message us with your numbers.

Our guide to day trips from Florence compares this tour with the Chianti day.

Questions people ask

Are drinks included at the winery lunch?

No. Lunch and any tastings are paid on the day, so you choose how much Vernaccia you want to try.

Can we add Monteriggioni?

Yes. It sits on the road between the two towns and adds about forty minutes.

Can we cancel?

Yes. Cancel up to 24 hours before pick-up and you get a full refund. See our cancellation page.

Booking the day

Check your date against the Palio and the cathedral floor, book your cathedral ticket, and pack for walking. Everything else is on the Siena and San Gimignano day trip page, where you choose the size of your group and book.

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