Guided Tours

Siena and San Gimignano Day trip from Florence

Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.

Group walking through vineyard on Siena, San Gimignano, and Chianti day trip.

Visitors at the steps of a historic church in San Gimignano, Italy.

Wine being poured into a glass during a Chianti tasting on a Florence day trip.

Duration

9 hr - 11 hr

Open today

10:00am - 07:00pm

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Book now, pay later

Book now without paying anything. Cancel for free if your plans change.

Guided tour

Transfers included

4.1/5

(844)

Adrianus

Jul 2025

Verified booking

4/5

Supervisors Martha and Julio provided perfect guidance. Clear in information and always approachable. TOP With a wine company, we expected a winery in the countryside. This was a factory site. So ambience was a bit less, despite the enthusiastic employee of the winery. Nice and enthusiastic. Despite the severe thunderstorm in Siena we had a nice day.

Robin

May 2025

Verified booking

4/5

We loved the three beautiful cities we visited, including the crown of Tuscany which wasn't on the itinerary. Paying to walk on the city walls was interesting and views were good, but we were on metal bridges, not the actual walls. There are two different access points so be sure to try both. Lunch was at a restaurant with a very small vineyard where we could walk and take photos. The tastings were all good but primarily a sales pitch. The pasta lunch was just ok. If you take the cathedral tour in Siena (recommended but additional cost) make sure you know how to get back to the meeting point!

Mihnea

Jun 2025

Verified booking

5/5

Our hosts Ilaria & Martina were friendly and well prepared with useful information about the places we visited during our trip. We loved all the cities, castles and nature we saw during that day and will be happy to come again for another tour.

Relax on an AC coach from Florence as you explore Siena and San Gimignano. Enjoy free time in both these cities and explore them independently.

An English-speaking tour leader will accompany you throughout your day trip to enrich your visit with insider tips, trivia, and more.

Stop at Siena and allow it to charm you with its Gothic elegance, narrow winding lanes, and the stunning shell-shaped Piazza del Campo. It’s small enough to explore in a few hours, yet packed with character.

Wander through the hilltop town of San Gimignano, admiring its towering structures and uncovering beautiful frescoes.

Full-day trip around Siena and San Gimignano

Multilingual assistance on board

Pick up from Florence

Free tine to explore Siena, a UNESCO World Heritage Site

Free time to explore San Gimignano

Round-trip AC coach transfer with Wi-Fi and USB charging on board

Guided tour of Siena city center (as per option selected)

Entry to Siena Cathedral and Piccolomini Library (as per option selected)

TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
Start point
Central Florence
Get direction
71 min by A/C Bus
78.3 km
1. Siena
2 attractions
Highlights
Banca Monte dei Paschi
Get direction
Siena Cathedral
Get direction
59 min by A/C Bus
45.5 km
2. Chianti Classico
1 activity
Things to do
Vineyard tour & wine tasting
Included in price
Tuscan lunch
55 min by A/C Bus
46.4 km
3. San Gimignano
1 attraction
Highlights
Torre Grossa
Get direction
70 min by A/C Bus
61.1 km
End point
Central Florence
Get direction
Your ending point would be same as your start point

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

4.1
844 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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Guests from United States, United Kingdom, Belgium and over 8 countries have loved this experience
What our guests say
Adrianus
Jul 2025
Verified booking
4/5
Supervisors Martha and Julio provided perfect guidance. Clear in information and always approachable. TOP With a wine company, we expected a winery in the countryside. This was a factory site. So ambience was a bit less, despite the enthusiastic employee of the winery. Nice and enthusiastic. Despite the severe thunderstorm in Siena we had a nice day.
Mihnea
Jun 2025
Verified booking
5/5
Our hosts Ilaria & Martina were friendly and well prepared with useful information about the places we visited during our trip. We loved all the cities, castles and nature we saw during that day and will be happy to come again for another tour.
Robin
May 2025
Verified booking
4/5
We loved the three beautiful cities we visited, including the crown of Tuscany which wasn't on the itinerary. Paying to walk on the city walls was interesting and views were good, but we were on metal bridges, not the actual walls. There are two different access points so be sure to try both. Lunch was at a restaurant with a very small vineyard where we could walk and take photos. The tastings were all good but primarily a sales pitch. The pasta lunch was just ok. If you take the cathedral tour in Siena (recommended but additional cost) make sure you know how to get back to the meeting point!
Milagro
May 2025
Verified booking
5/5
A lot of history in each of the towns, beautiful scenery, and comfortable rides.
Jose
Mar 2025
Verified booking
5/5
Everything was neat, the guide explained excellent everything we saw on the tour, the times in the places were perfect and the wine tasting and food was perfect, we would do the tour again.

Treat yourself to a full day exploring Tuscany's UNESCO Heritage Sites, cruising in comfort aboard an air-conditioned coach from Florence.

A well-curated itinerary

Siena

Embark on an adventure from Florence, starting with Siena. If selected, meet your knowledgeable local guide who will lead you on a comprehensive tour of the historic center. Begin at the magnificent Basilica of San Domenico, a Renaissance masterpiece dedicated to St. Catherine of Siena. Wander through narrow medieval streets lined with splendid palaces, reach the iconic Piazza del Campo, and marvel at the focal point—the Palazzo Pubblico (Town Hall). Continue to the awe-inspiring 12th-century cathedral, where you can explore its majestic architecture and vibrant polychrome marbles during an optional inside visit.

San Gimignano

Next, journey towards the enchanting San Gimignano, a world-renowned walled town perched on a hilltop. This medieval gem, adorned with towering structures, captivating frescoes, and priceless artworks, will be your last stop. Get free time to soak in the unique atmosphere of this architectural wonder before returning to Florence.

Siena Cathedral

Monday	10:00am - 07:00pm	last entry 06:30pm
Tuesday	10:00am - 07:00pm	last entry 06:30pm
Wednesday	10:00am - 07:00pm	last entry 06:30pm
Thursday	10:00am - 07:00pm	last entry 06:30pm
Friday	10:00am - 07:00pm	last entry 06:30pm
Saturday	10:00am - 07:00pm	last entry 06:30pm
Sunday	01:30pm - 06:00pm	last entry 05:30pm

Accessibility

This experience is not accessible by wheelchair and pram/strollers.

Additional information

This tour involves a fair amount of walking, so comfortable shoes are highly recommended.

Safety is a priority, so the wine-tasting experience is restricted for guests under the age of 18 years.

Guests under 18 years can join the tour if they are each accompanied by at least one adult.

For entry to Siena Cathedral, all guests must wear clothing that covers the knees and shoulders.

Your voucher will be emailed to you instantly.

Please arrive at the meeting point 20 minutes before the scheduled time of your tour to avoid any delays.

Display the voucher on your mobile phone with a valid photo ID at the meeting point.

Meeting point

Please check your final voucher for the meeting point details and specific instructions.