Florence To Siena Tours

Take a day trip from Florence to Siena, a UNESCO medieval gem and top destination in Tuscany.

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Why head out with Headout

Person walking towards Siena Cathedral in Tuscany, Italy, surrounded by greenery.

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

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

Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.

Tour bus parked among cypress trees in Tuscany, Italy.

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

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

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

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

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

Leaning Tower of Pisa with Pisa Cathedral on the left during a walking tour.

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

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

San Gimignano town square with medieval buildings and tourists exploring.

Person serving bruschetta during a Tuscany food tour.

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

Free cancellation

Book now, pay later

11 hrs 30 mins - 13 hrs 45 mins

2 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 Palazzo Pubblico.

Streets of San Gimignano with historic stone buildings and tourists exploring.

Vineyards and olive groves in Chianti region, Tuscany, Italy.

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

Wine barrels in a cellar during Chianti wine tasting tour from Florence.

Tour guide holding a sign in a Chianti village during a wine tour from Florence.

Bus interior with passengers traveling from Tromso to Skjervoy.

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

Free cancellation

Book now, pay later

10 hrs 30 mins - 11 hrs 30 mins

1 more

Visit Siena, San Gimignano, and Chianti in one well-paced day trip from Florence.
Enjoy a winery visit in the Chianti countryside with 3 wine tastings included.
Get free time in both Siena and San Gimignano to explore at your own pace.
Upgrade to a guided walking tour of Siena for deeper insight into its history and landmarks.
Travel comfortably with round-trip transfers and a multilingual tour leader.

More details

Visit Siena, San Gimignano, and Chianti in one well-paced day trip from Florence.
Enjoy a winery visit in the Chianti countryside with 3 wine tastings included.
Get free time in both Siena and San Gimignano to explore at your own pace.
Upgrade to a guided walking tour of Siena for deeper insight into its history and landmarks.
Travel comfortably with round-trip transfers and a multilingual tour leader.

from €65

€48.75

25% off

Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.

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

Pisa Cathedral and Baptistery with tourists exploring the square.

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

People dining at a long table during Pisa, Siena, and San Gimignano day trip.

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

Bus traveling through Chianti vineyards during Florence wine tour.

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

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

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

Siena Cathedral interior with striped columns and ornate vaulted ceiling.

Tourists inside Siena Cathedral admiring frescoes and architecture, Italy.

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

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Free cancellation

Book now, pay later

11 hrs 30 mins - 12 hrs

2 more

Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.
Enjoy free time in Pisa, San Gimignano, and Siena to explore at your own pace.
Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.
Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.
Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

More details

Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.
Enjoy free time in Pisa, San Gimignano, and Siena to explore at your own pace.
Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.
Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.
Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

from €93.20

€69.90

25% off

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

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

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.

Aerial view of Chianti winery with vineyards and Tuscan landscape.

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

From Florence: Siena & San Gimignano Day Trip with Wine Tastings & Lunch

Free cancellation

Book now, pay later

9 hrs - 11 hrs

2 more

Discover two of Tuscany’s most iconic hill towns in one relaxed day trip from Florence.
Enjoy free time in both Siena and San Gimignano to explore at your own pace.
Taste regional flavors with a winery visit, 3 wine tastings, and a traditional Tuscan meal.
Upgrade to a guided Siena tour with optional Cathedral access for a deeper cultural experience.
Travel comfortably with round-trip AC transport and a multilingual tour leader.

More details

Discover two of Tuscany’s most iconic hill towns in one relaxed day trip from Florence.
Enjoy free time in both Siena and San Gimignano to explore at your own pace.
Taste regional flavors with a winery visit, 3 wine tastings, and a traditional Tuscan meal.
Upgrade to a guided Siena tour with optional Cathedral access for a deeper cultural experience.
Travel comfortably with round-trip AC transport and a multilingual tour leader.

from

€79

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What our guests say

Christopher C

Couple

Last week

Excellent tour guide in Igna and driver Luca. Both were excellent as was the tour. Highly recommended and very good value. Ciao Florence had some admin issues though

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

Shubham S

India

Family

3 weeks ago

While the tour in itself was good, I was surprised that we didnt go to Pisa. The heading says we go to Piss. Chiara was a great guidez

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

Victor M

Argentina

Couple

3 weeks ago

Everything was great—the guide did a wonderful job explaining each place. The vineyard is a beautiful spot, and the staff were so friendly. And finally, Pisa, with its 200-plus steps... Everything was fantastic... Kudos to our guide Marina...

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Rubén A

Group

Mar 2026

It was a truly wonderful tour. Our driver, Daniel, was a true professional, and our guide, Constantino, was very friendly and made the tour enjoyable by providing us with useful information throughout. A day to remember

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

Adriana V

Cayman Islands

Couple

Mar 2026

I really liked how easy it was to get there. I didn't like the amount of time allotted for lunch. Eating lasagna and tasting wines in just an hour was terrible. I suggest simply spacing things out better.

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