Siena, San Gimignano & Chianti Small-Group Day Trip from Florence
- Duration9 hours
- Daily
- Group
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Overview
This small-group day trip from Florence, with up to 25 travellers, takes you to the two most loved hill towns of Tuscany and the countryside between them. After a scenic drive you explore Siena with an English-speaking guide, from its medieval streets to the shell-shaped Piazza del Campo, then have free time on your own. Next, the minibus crosses the Chianti hills of olive groves and cypress trees to a family-run estate for a traditional Tuscan lunch. The day ends in San Gimignano, the town of medieval towers, with free time to stroll its main street and squares before returning to Florence in the late afternoon. Departure is at 08:00 from Piazzale Montelungo; there is no hotel pickup.
Highlights
- Small group of up to 25 travellers
- Guided walking tour of Siena with an English-speaking guide
- Piazza del Campo, the stage of the famous Palio horse race
- Scenic drive through the Chianti hills
- Traditional Tuscan lunch at a family-run countryside estate
- Free time among the medieval towers of San Gimignano
- Return transport by air-conditioned minibus or minivan
Full Description
Siena: medieval streets and Piazza del Campo
Siena was one of the great republics of medieval Italy, and its centre, a UNESCO World Heritage Site, has kept the brick palaces, steep lanes and city districts of that time. Your guide leads a walk of about 75 minutes through the narrow streets to Piazza del Campo, the shell-shaped square that slopes down to the Gothic Palazzo Pubblico and its slender Torre del Mangia, with the marble Fonte Gaia fountain at the top.
The square hosts the Palio, the bareback horse race between the city's districts held every 2 July and 16 August. The guide also points out the striped marble cathedral; entry to it is not included on this tour. You then have about an hour of free time in Siena for a coffee, shopping or simply sitting on the warm bricks of the Campo.
The Siena Cathedral and the city's districts
Siena's cathedral, with its black-and-white striped bell tower and richly carved facade, is one of the finest Gothic churches in Italy, famous for its inlaid marble floor and its painted library. The cathedral is not part of the standard tour and is closed to visitors on Sundays and during religious celebrations, but you will see its exterior and square on the guided walk.
The city is still divided into historic districts, each with its own flag, symbol, church and fountain, and you will notice their colours on walls and lanterns as you walk. Learning about this living tradition from your guide is one of the reasons why a Siena day trip from Florence is so rewarding.
The Chianti countryside and Tuscan lunch
Between Siena and San Gimignano the road crosses the classic Tuscan landscape: soft hills, olive groves, rows of cypress trees and old stone farmhouses. This is the scenery many travellers picture when they think of Tuscany, and the drive itself is a highlight of this Chianti tour from Florence.
Lunch is served at a family-owned countryside estate, a relaxed stop of about an hour and a half. The typical menu includes Tuscan cold cuts and cheeses, bruschetta with the estate's own olive oil, pasta or soup and a dessert; a vegetarian menu can be prepared if you request it when booking. It is a warm taste of Tuscan country hospitality.
San Gimignano: the town of medieval towers
San Gimignano rises on its hill above the Elsa valley with a skyline of tall stone towers, built by rival families in the Middle Ages as symbols of wealth and power. Its historic centre is a UNESCO World Heritage Site, and its walls, gates and squares have changed little in centuries.
You have about an hour and a half of free time to explore on your own: walk the main street with its shops, see Piazza della Cisterna with its old well, visit the Collegiata, the main church with its frescoed walls, or enjoy a gelato. In the late afternoon the minibus drives you back to Florence, arriving about 75 minutes later.
Itinerary
- Departure from Piazzale Montelungo, FlorenceArrive about 15 minutes early for the 08:00 departure by air-conditioned minibus.
- Drive to SienaAbout an hour to an hour and a half through the Tuscan countryside.
- Guided walk in SienaAbout 75 minutes through the medieval centre to Piazza del Campo with your guide.
- Free time in SienaAbout an hour on your own for a coffee, shopping or photos.
- Tuscan lunch in the Chianti hillsA drive of about 35 minutes to a family-run countryside estate for a traditional lunch of about 1.5 hours.
- San GimignanoAbout 1.5 hours of free time among the medieval towers and squares.
- Return to FlorenceAbout 75 minutes back to Piazzale Montelungo, arriving in the late afternoon.
What's included
- Small group of up to 25 travellers
- English-speaking professional guide and driver
- Return transport from Florence by air-conditioned minibus or minivan
- Guided walking tour of Siena's highlights and free time in Siena
- Traditional Tuscan lunch at a family-run countryside estate
- Free time in San Gimignano
Not included
- Siena Cathedral entry and guided visit
- Hotel pickup and drop-off
- Tips
Is this right for you?
Great for
- Food lovers
- Travellers who want a proven choice — rated 4.9/5 by past travellers
Think twice if
- You want a private tour — this one is shared with other travellers
Not suitable for
- People with mobility impairments
- Wheelchair users
Meeting point
Meet your guide at Piazzale Montelungo in Florence, at the foot of the tallest red-brick building, opposite the car park, about an 8-minute walk from Santa Maria Novella station. Look for the guide's red flag. If you use a map app, do not follow a route through the station building, as that exit is closed. Please arrive 15 minutes before the 08:00 departure; there is no hotel pickup.
Important information
- Departure is at 08:00; please arrive 15 minutes early
- Bring a passport or ID card
- Wear comfortable shoes and weather-appropriate clothing; Siena and San Gimignano are hilly
- Siena Cathedral entry is not included and the cathedral is closed to visitors on Sundays and during religious celebrations
- A vegetarian menu is available if requested when booking
- The tour runs rain or shine
- Cruise passengers docking at Livorno or La Spezia: the drive to Florence takes about 2 hours, so check your ship times and arrange your own transport
- Not suitable for wheelchair users or people with mobility impairments
Good to know
Frequently Asked Questions
Straight answers to what travellers ask us most, before they book.
Is this a shared or a private experience?
It is a shared small-group day trip with up to 25 travellers.
How long does it take?
About 9 hours, from the 08:00 departure to the late-afternoon return in Florence.
Is hotel pickup included?
No. The tour starts and ends at Piazzale Montelungo, close to Santa Maria Novella station.
What is included?
Transport by air-conditioned minibus, an English-speaking guide and driver, a guided walk in Siena, free time in Siena and San Gimignano, and a traditional Tuscan lunch.
Is the price per person or per group?
The price is per person, with a reduced rate for children aged 4 to 12. The booking panel on this page shows the current price.
Is it suitable for children and people with reduced mobility?
Children enjoy the towns and the countryside, but there is a lot of walking on hills and cobbles, so it is not suitable for wheelchair users or people with mobility impairments.
Can I visit Siena Cathedral?
Cathedral entry is not included. You can see it from outside on the guided walk; it is closed to visitors on Sundays.
What is served for lunch?
A traditional Tuscan menu of cold cuts, cheeses, bruschetta with olive oil, pasta or soup and dessert. A vegetarian menu is available on request.
Is this tour good for a Siena and San Gimignano day trip from Florence?
Yes, it covers both towns and the Chianti countryside in one comfortable day with a guide and transport.
What happens in bad weather?
The tour runs rain or shine, so bring an umbrella or jacket if rain is expected.
What should I bring?
Passport or ID, comfortable shoes, weather-appropriate clothing and a camera.
How do I book and confirm?
Choose your date on this page and send your booking. Our team confirms it on WhatsApp within minutes.
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