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Experience the best tours of Tuscany from Florence

Escape Florence to Tuscany, the birthplace of Italian Renaissance, and enjoy its famous wines.
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Slide 1 of 7, Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
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 Original price€65
€55.25

15% off

Slide 1 of 7, Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
5 hrs
1 more
  • Escape Florence for the rolling vineyards and scenic countryside of Tuscany’s celebrated Chianti wine region.

  • Visit 2 traditional Chianti wineries and enjoy 6 wine tastings with snacks, including regional wines and local flavors.

  • Learn about Chianti’s winemaking traditions, grape varieties, and production methods from expert hosts during your visits.

  • Travel comfortably with round-trip AC coach transfers, onboard Wi-Fi, and a licensed tour escort throughout the experience.

  • Enjoy a relaxed group experience with fellow wine lovers while discovering Tuscany’s iconic vineyard landscapes.

More details
  • Escape Florence for the rolling vineyards and scenic countryside of Tuscany’s celebrated Chianti wine region.

  • Visit 2 traditional Chianti wineries and enjoy 6 wine tastings with snacks, including regional wines and local flavors.

  • Learn about Chianti’s winemaking traditions, grape varieties, and production methods from expert hosts during your visits.

  • Travel comfortably with round-trip AC coach transfers, onboard Wi-Fi, and a licensed tour escort throughout the experience.

  • Enjoy a relaxed group experience with fellow wine lovers while discovering Tuscany’s iconic vineyard landscapes.

from
€33.15
Slide 1 of 17, Visitors entering Poggio ai Laghi winery in Chianti, Italy.
Visitors entering Poggio ai Laghi winery in Chianti, Italy.
12 hrs 15 mins
2 more
  • Visit Pisa, Siena, San Gimignano, and Chianti in one day with comfortable round-trip transfers from Florence.

  • Enjoy free time in each destination to explore famous landmarks, browse local shops, or relax at a café at your own pace.

  • Capture iconic views of Pisa’s Leaning Tower and wander through Siena’s historic center, a UNESCO World Heritage Site.

  • Upgrade your experience with a Chianti winery visit featuring 3 wine tastings and a traditional Tuscan lunch.

  • Choose a guided tour upgrade to uncover Siena’s history and explore the magnificent Siena Cathedral with an expert guide.

More details
  • Visit Pisa, Siena, San Gimignano, and Chianti in one day with comfortable round-trip transfers from Florence.

  • Enjoy free time in each destination to explore famous landmarks, browse local shops, or relax at a café at your own pace.

  • Capture iconic views of Pisa’s Leaning Tower and wander through Siena’s historic center, a UNESCO World Heritage Site.

  • Upgrade your experience with a Chianti winery visit featuring 3 wine tastings and a traditional Tuscan lunch.

  • Choose a guided tour upgrade to uncover Siena’s history and explore the magnificent Siena Cathedral with an expert guide.

from
€49
Slide 1 of 15, Person walking towards Siena Cathedral in Tuscany, Italy, surrounded by greenery.
Person walking towards Siena Cathedral in Tuscany, Italy, surrounded by greenery.
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
Slide 1 of 11, Tootbus Tuscany tour bus parked near cypress trees in Tuscany, Italy.
Tootbus Tuscany tour bus parked near cypress trees in Tuscany, Italy.
Explore at your pace
  • Explore Tuscany at your own pace with unlimited travel between Florence, Pisa, Siena, Lucca, and San Gimignano.

  • Switch between two scenic routes connecting historic cities, countryside views, and UNESCO-listed towns.

  • Start your journey from any city, at any time, with flexible boarding across all scheduled departures.

  • Stay connected and informed onboard with Wi-Fi, charging ports, and an AI-powered multilingual guide.

  • Choose from 2, 3, or 5-day passes depending on how deeply you want to explore the region.

More details
  • Explore Tuscany at your own pace with unlimited travel between Florence, Pisa, Siena, Lucca, and San Gimignano.

  • Switch between two scenic routes connecting historic cities, countryside views, and UNESCO-listed towns.

  • Start your journey from any city, at any time, with flexible boarding across all scheduled departures.

  • Stay connected and informed onboard with Wi-Fi, charging ports, and an AI-powered multilingual guide.

  • Choose from 2, 3, or 5-day passes depending on how deeply you want to explore the region.

from Original price€89
€62.30

30% off

Slide 1 of 13, Tour guide explaining Pisa Cathedral and Leaning Tower of Pisa, Italy.
Tour guide explaining Pisa Cathedral and Leaning Tower of Pisa, Italy.
6 hrs
1 more
  • Sit back and relax with round-trip AC coach transfers from Florence to Pisa, no planning, no stress.

  • Enjoy the convenience of a multilingual escort throughout the journey before setting off to explore Pisa independently.

  • Spend around 2.5 hours in Pisa, exploring its historic streets and capturing iconic photos of the Leaning Tower and Cathedral.

  • Upgrade your day by adding Leaning Tower fast-track access and/or guided entry to the cathedral, baptistery, Camposanto and the museums.

More details
  • Sit back and relax with round-trip AC coach transfers from Florence to Pisa, no planning, no stress.

  • Enjoy the convenience of a multilingual escort throughout the journey before setting off to explore Pisa independently.

  • Spend around 2.5 hours in Pisa, exploring its historic streets and capturing iconic photos of the Leaning Tower and Cathedral.

  • Upgrade your day by adding Leaning Tower fast-track access and/or guided entry to the cathedral, baptistery, Camposanto and the museums.

from Original price€39
€33.15

15% off

Slide 1 of 11, Guide talking to a couple in front of Pisa Cathedral and Leaning Tower, Italy.
Guide talking to a couple in front of Pisa Cathedral and Leaning Tower, Italy.
11 hrs 30 mins - 12 hrs 15 mins
2 more
  • Explore Pisa, Siena, San Gimignano, and Chianti in a small group of no more than 20 guests for a more intimate and relaxed experience.

  • Enjoy free time in Tuscany's most iconic towns, with fewer people and more opportunities to connect with your tour leader and fellow travelers.

  • Visit a Chianti winery and sample three regional wines while learning about the traditions behind Tuscany's world-famous winemaking.

  • Sit down to a traditional Tuscan lunch surrounded by rolling vineyards and postcard-worthy countryside scenery.

  • Upgrade to a guided tour of Siena for expert insights into its medieval history, famous piazza, and centuries-old traditions.

More details
  • Explore Pisa, Siena, San Gimignano, and Chianti in a small group of no more than 20 guests for a more intimate and relaxed experience.

  • Enjoy free time in Tuscany's most iconic towns, with fewer people and more opportunities to connect with your tour leader and fellow travelers.

  • Visit a Chianti winery and sample three regional wines while learning about the traditions behind Tuscany's world-famous winemaking.

  • Sit down to a traditional Tuscan lunch surrounded by rolling vineyards and postcard-worthy countryside scenery.

  • Upgrade to a guided tour of Siena for expert insights into its medieval history, famous piazza, and centuries-old traditions.

from
€149
Slide 1 of 7, Group riding Vespas on a guided tour through Tuscany countryside from Florence.
Group riding Vespas on a guided tour through Tuscany countryside from Florence.
7 hrs
  • Ride a stylish Vespa through Tuscany – Cruise past vineyards, rolling hills, and scenic roads on an iconic Italian scooter.

  • Pass through scenic countryside viewpoints offering breathtaking panoramic views.

  • Relish traditional Tuscan flavors crafted with fresh, local ingredients.

  • Ride stress-free with a local guide, radio communication, and all essentials provided.

More details
  • Ride a stylish Vespa through Tuscany – Cruise past vineyards, rolling hills, and scenic roads on an iconic Italian scooter.

  • Pass through scenic countryside viewpoints offering breathtaking panoramic views.

  • Relish traditional Tuscan flavors crafted with fresh, local ingredients.

  • Ride stress-free with a local guide, radio communication, and all essentials provided.

from
€150
Slide 1 of 13, Tourists taking a selfie with Siena skyline in the background, featuring Torre del Mangia, Tuscany.
Tourists taking a selfie with Siena skyline in the background, featuring Torre del Mangia, Tuscany.
12 hrs
2 more
  • Discover Tuscany in all its beauty and glory with this guided tour and get a wholesome cultural experience.

  • Explore landscapes, art masterpieces, old towns, culinary goodness, and wine tasting - all in this one tour.

  • Start the tour at Siena amidst the vineyards and olive groves and discover the magnificent sight of Piazza del Campo.

  • Move on to a UNESCO World Heritage Site, San Gimignano, and explore its cobbled streets and glorious skyline.

  • Take a break and have a delicious Tuscan lunch at Chianti hills with a wine tasting session.

  • End the tour on a high by visiting the Leaning Tower of Pisa.

More details
  • Discover Tuscany in all its beauty and glory with this guided tour and get a wholesome cultural experience.

  • Explore landscapes, art masterpieces, old towns, culinary goodness, and wine tasting - all in this one tour.

  • Start the tour at Siena amidst the vineyards and olive groves and discover the magnificent sight of Piazza del Campo.

  • Move on to a UNESCO World Heritage Site, San Gimignano, and explore its cobbled streets and glorious skyline.

  • Take a break and have a delicious Tuscan lunch at Chianti hills with a wine tasting session.

  • End the tour on a high by visiting the Leaning Tower of Pisa.

from Original price€239
€172.08

28% off

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What our guests say

Coda S

Ecuador
Solo
Sep 2026
The guide's tips on key spots. Like the most delicious ice cream I've ever tasted in my life, in San Gimignano 🙌✨

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

Yang Z

China
Couple
Jun 2026

+6 more

Alex is an incredibly warm and friendly guide! We absolutely loved this day trip to Siena, San Gimignano, and Monteriggioni. For me, visiting the actual locations from Ezio Auditore’s story was a real pilgrimage. As for the €22 lunch, it was fine, but if you prefer more freedom, feel free to choose your own restaurant—just make sure to be on time for the meeting. Finally, if you have the chance to visit a winery in Chianti, you absolutely must try Firmina. It’s a truly interesting wine to drink!

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

Pinelopi A

Greece
Group
Jul 2026
Although we lost half of the trip because we could not find the meeting point we managed to find our group and live the experience at sienna ! The girls at the meeting point were very polite and helped me book train tickets to find the other people of my group. Barbara was super guide and kind! Thanks also rachel from headout chat who gave me some credits for another trip. I am grateful.

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

Fabrizio T

Italy
Solo
Jun 2026

+4 more

An exciting experience. Highly recommended and impeccably organized from start to finish. One of the highlights was Sandro, our guide. Professional, empathetic, engaging, and tireless. You can tell he loves his job. Lucky him—and lucky are those who get to work with him. I’d also put Adele, the guide who welcomed us in Siena, on the same level. Professional, engaging, empathetic, and special. She makes you want to return to Siena tomorrow to discover the countless things this Tuscan gem has yet to reveal to a fly-by visitor—things that she, as a true Sienese, surely knows.

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

Marvin B

United States
Couple
Jul 2026

+3 more

Constanino and Valentino were excellent: smooth ride without incident; insights without being overbearing. Loved it. Would definitely recommend!

From Florence: Pisa Half-Day Trip

Zuzanna B

Belgium
Couple
Jul 2026

+2 more

We did the Chianti wine tour and it was incredible! Our guide Ms Ezgi was very enthousiast to share her knowledge of the region with us in a very professional way.The wines were very tasty. The views were breath taking. Really recommend doing this tour especially if you are a Witcher 3 Blood and Wine fan!!

From Florence: Chianti Wineries Tour with Wine Tasting

Victoria H

Colombia
Couple
Jun 2026
Everything from the beginning was awesome. Logistic, samples, places. All the people was so nice and welcoming. I really enjoy this experiencie with my husband in our honeymoon trip

From Florence: Chianti Wineries Tour with Wine Tasting

Didot M

France
Family
Aug 2026
Absolutely great—the driver was fantastic and took really good care of us. We had the bus all to ourselves, which was nice. Very welcoming—I highly recommend it. Thanks again for everything.

Tuscany Bus Pass: Unlimited Travel Between 5 Cities

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