Florence To Siena Tours

Visit the walled city of Siena, a historic banking city in the Tuscan region, and learn about its medieval architecture and history with a local guide. Explore guided tours and day trip options to visit Siena and other Italian cities like Pisa and San Gimignano.

4.4/5

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Aerial view of Siena's historic rooftops and cathedral in Tuscany, Italy.

Tour bus parked among cypress trees in Tuscany, Italy.

Tourists boarding a bus for the Tuscany in a Day tour, visiting Siena, San Gimignano, and Pisa.

Tourists taking a selfie in front of a historic building in Siena, Italy.

Piazza del Campo in Siena with Torre del Mangia, Tuscany.

Tourists posing near the Leaning Tower of Pisa, Italy.

Leaning Tower of Pisa and Pisa Cathedral in Tuscany, Italy.

Siena Cathedral facade with visitors in Tuscany, Italy.

San Gimignano town square with medieval buildings and tourists exploring.

Siena Cathedral facade with intricate Gothic architecture, Tuscany.

Group enjoying wine tasting in a Tuscan winery, Tuscany in a Day tour.

Bottles of Tuscan wine on a wooden table, featuring Chianti and Vernaccia di San Gimignano.

Wine glasses raised in a toast during a Tuscany tour in Siena, San Gimignano, and Pisa.

Person serving bruschetta during a Tuscany food tour.

Wine tasting in a Tuscan cellar with pasta, part of the Tuscany in a Day tour.

Group enjoying wine tasting in Tuscany during Siena, San Gimignano, and Pisa tour.

San Gimignano skyline with medieval towers under a blue sky, Tuscany, Italy.

Tourists walking through a vineyard with San Gimignano towers in the background, Tuscany.

Horse race at Siena's Palio, Tuscany, with riders in colorful attire.

4.5(2,026)

Guided Tours

Free cancellation

Instant confirmation

11 hr 30 min

3 more

Discover the Tuscan experience with its lyrical landscapes and edgy world-class art, with a guide in the language of your choice!
Visit the walled hill city of Siena, known for its medieval appeal and Gothic appearance. Check out the Piazza del Campo, known famously to hold the Palio Horse Race every year.
Explore the World Heritage Site of San Gimignano, an eternally sought-after destination with its skyline of medieval towers.
Discover Pisa and its renowned charm with places like Piazza dei Miracoli, and the famous Leaning Tower.
Enjoy a delicious Tuscan lunch with a local wine-tasting tour amidst the rolling hills in the Chianti region.

More details

Discover the Tuscan experience with its lyrical landscapes and edgy world-class art, with a guide in the language of your choice!
Visit the walled hill city of Siena, known for its medieval appeal and Gothic appearance. Check out the Piazza del Campo, known famously to hold the Palio Horse Race every year.
Explore the World Heritage Site of San Gimignano, an eternally sought-after destination with its skyline of medieval towers.
Discover Pisa and its renowned charm with places like Piazza dei Miracoli, and the famous Leaning Tower.
Enjoy a delicious Tuscan lunch with a local wine-tasting tour amidst the rolling hills in the Chianti region.

from

€65

Piazza del Campo in Siena with Torre del Mangia and historic buildings.

Streets of San Gimignano with medieval towers and cobblestone paths in Tuscany, Italy.

Vineyards and olive groves in Chianti region, Tuscany, Italy, viewed during a wine tour from Florence.

Hand holding a glass of rosé wine in a Chianti vineyard during e-bike tour.

Siena cathedral, San Gimignano towers, Monteriggioni walls, Chianti vineyards on Florence tour.

A tour escort waiting to meet tourist at the meeting point

Bus transfer from Tromso to Skjervoy with scenic Arctic landscapes in Norway.

New

Guided Tours

Free cancellation

Instant confirmation

11 hr 30 min

3 more

Travel in style with round-trip transfers from Florence by GT coach, complete with seamless multilingual support.
Experience Siena’s rich history on a guided tour, from the stunning Palazzo Pubblico to the iconic Torre del Mangia in the lively Piazza del Campo.
Wander amidst the medieval towers of San Gimignano, a UNESCO World Heritage Site, and let your curiosity lead the way through its historic streets.
Delight in the world of Chianti as you stroll through a local estate, uncovering the secrets of wine making. Cap your experience with a hearty 3-course Tuscan lunch.

More details

Travel in style with round-trip transfers from Florence by GT coach, complete with seamless multilingual support.
Experience Siena’s rich history on a guided tour, from the stunning Palazzo Pubblico to the iconic Torre del Mangia in the lively Piazza del Campo.
Wander amidst the medieval towers of San Gimignano, a UNESCO World Heritage Site, and let your curiosity lead the way through its historic streets.
Delight in the world of Chianti as you stroll through a local estate, uncovering the secrets of wine making. Cap your experience with a hearty 3-course Tuscan lunch.

from

€89

Siena cityscape with historic buildings and lush greenery during Chianti wine tour.

Tour guide speaking to tourists in a historic street during Pisa, Siena, and San Gimignano day trip.

Woman on a historic balcony with frescoes in San Gimignano, Italy.

Pisa Cathedral and Baptistery with tourists exploring the square.

Women posing playfully with the Leaning Tower of Pisa in Italy.

Bus traveling through Chianti vineyards during Florence wine tour.

Aerial view of Chianti winery with vineyards and Tuscan landscape.

Tourists enjoying a wine tasting experience in Tuscany during a Pisa, Siena, and San Gimignano day trip.

Wine bottles and Italian appetizers on a table during a Pisa, Siena, San Gimignano & Chianti day trip.

Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.

Siena Cathedral facade with tourists during the day in Siena, Italy.

Tour group inside Siena Cathedral with striped columns and stained glass window.

Tour group with guide at Piazza del Campo, Siena, Italy, with historic buildings in background.

4.4(3,894)

Guided Tours

Free cancellation

Instant confirmation

12 hr

3 more

Take a round-trip from Florence to explore Pisa, San Gimignano, and Siena, with photo ops at the Leaning Tower, a Tuscan lunch, and an optional guided cathedral tour at Siena.
Experience a spacious ride to and from Florence with dedicated multilingual assistance on board.
Begin in Pisa with a visit to the Square of Miracles, where you’ll have plenty of time to pose with the iconic Leaning Tower.
Enjoy a satisfying lunch with top-notch wines in San Gimignano, then explore its historic 13th-century walls and stone towers.
Discover the allure of Siena’s medieval squares, with the option to enrich your experience by adding a guided tour of the city and its cathedral.

More details

Take a round-trip from Florence to explore Pisa, San Gimignano, and Siena, with photo ops at the Leaning Tower, a Tuscan lunch, and an optional guided cathedral tour at Siena.
Experience a spacious ride to and from Florence with dedicated multilingual assistance on board.
Begin in Pisa with a visit to the Square of Miracles, where you’ll have plenty of time to pose with the iconic Leaning Tower.
Enjoy a satisfying lunch with top-notch wines in San Gimignano, then explore its historic 13th-century walls and stone towers.
Discover the allure of Siena’s medieval squares, with the option to enrich your experience by adding a guided tour of the city and its cathedral.

from

€65

Aerial view of San Gimignano with medieval towers and surrounding countryside.

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.

Tourists taking a selfie in front of historic architecture in San Gimignano, Italy.

Aerial view of Monteriggioni's medieval walls and surrounding Tuscan landscape.

Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.

4.1(844)

Guided Tours

Free cancellation

Instant confirmation

9 hr

3 more

Relax on an AC coach from Florence as you explore Siena, San Gimignano, and Chianti—enjoy free time and a winery lunch with local craft tastings.
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.
Visit a charming Chianti winery, where you'll enjoy a delectable 3-course lunch complemented by a range of exquisite wines.
Wander through the hilltop town of San Gimignano, admiring its towering structures and uncovering beautiful frescoes.
Between April and October, the tour may include a stop at the walled commune of Monteriggioni.

More details

Relax on an AC coach from Florence as you explore Siena, San Gimignano, and Chianti—enjoy free time and a winery lunch with local craft tastings.
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.
Visit a charming Chianti winery, where you'll enjoy a delectable 3-course lunch complemented by a range of exquisite wines.
Wander through the hilltop town of San Gimignano, admiring its towering structures and uncovering beautiful frescoes.
Between April and October, the tour may include a stop at the walled commune of Monteriggioni.

from

€53.10

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Millions love heading out with us

John

5/5

We had a very great tour. Our guide Assia was excellent! She was informative and kept our group moving. Highly recommend.

Guided tour of Siena, San Gimignano & Monteriggioni with Wine Tasting in Chianti

Mária

5/5

It was a great experience and we enjoyed it a lot. We visited 3 towns, had a tasty lunch and a wine degustation - all with a very nice tour guide. I recommend this trip a lot.

Guided tour of Siena, San Gimignano & Monteriggioni with Wine Tasting in Chianti

Christina

4/5

South Africa

We absolutely loved the locations! It was easy to get our tickets, they had a good mix of free time, wine tasting and lunch and the option of a walking and cathedral tour in Siena. The tour guide did a really good job of managing a large group but it was a mission to get such a large group all back at the same time which was frustrating. Nice tour but if you don't like large groups, rather visit the locations on your own.

From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip

Chris

5/5

Ireland

Federico worked very hard to make sure we all were getting the most out of the trip. We had plenty of time to do our own thing at the various stops. The ticketing process was very easy also.

From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip

Adrianus

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.

From Florence: Siena, San Gimignano & Chianti Day Trip with Lunch & Curated Countryside Sips

Robin

4/5

United States

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!

From Florence: Siena, San Gimignano & Chianti Day Trip with Lunch & Curated Countryside Sips

Juan

4/5

United States

The tour was very nice. My mother and I really enjoyed all the places we visited. Lunch in San Gimignano was delicious, accompanied by local Tuscan products, which made the experience even more special. For those who prefer to tour the towns without any rush, we suggest doing it on your own. Finally, we would like to thank immensely the help offered by the guide Alexandra who very kindly helped us find a place to leave our luggage in Siena as we were not ending the tour in Florence as scheduled, but were heading to another destination. Without his help we would not have known Siena. Excellent as a professional and as a person.

From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Tuscan Tastings

Prachi

5/5

India

Hi, My experience with Headout team and the guide was suoer amazing, I think on our own we wouldn't have ever visited so many places in one day, but due to this trip we could visit so much and the guide was also very informative. I speacially love the wine tasting experience. Wish we would have got more time everywhere but it was a little hectic but worth visting ..I just loved it.

From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Tuscan Tastings