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    Explore Siena

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    Siena Cathedral

    Palazzo Pubblico

    Tower of Mangia, Siena

    Brolio Castle

    Cripta del Duomo di Siena

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    Santa Maria della Scala

    Piccolomini Library

    Piazza del Duomo, Siena

    Facciatone

    Museo Civico, Siena

    Piazza del Campo

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    Florence Duomo ComplexAttraction in Florence, Italy

    Ponte VecchioAttraction in Florence, Italy

    Piazza della SignoriaAttraction in Florence, Italy

    Uffizi GalleryAttraction in Florence, Italy

    Accademia GalleryAttraction in Florence, Italy

    Porta del ParadisoAttraction in Florence, Italy

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    Things to do in Florence

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  • Explore Siena
  • Places to see
  • Things to do
  • Top sights
  • Attraction types
  • Outside Siena

Siena Cathedral

Palazzo Pubblico

Tower of Mangia, Siena

Brolio Castle

Cripta del Duomo di Siena

Monte dei Paschi di Siena

Santa Maria della Scala

Piccolomini Library

Piazza del Duomo, Siena

Facciatone

Museo Civico, Siena

Piazza del Campo

Day trips

Landmarks & monuments

UNESCO sites

Castle & palace tours

Multi-day trips

Shore excursions

Nearby destinations

Florence tours

Pisa tours

San Gimignano tours

Monteriggioni tours

Montepulciano tours

Livorno tours

Nearby sights

Florence Duomo ComplexAttraction in Florence, Italy

Ponte VecchioAttraction in Florence, Italy

Piazza della SignoriaAttraction in Florence, Italy

Uffizi GalleryAttraction in Florence, Italy

Accademia GalleryAttraction in Florence, Italy

Porta del ParadisoAttraction in Florence, Italy

  • Top experiences
  • Interests
  • Outside Siena

Cooking classes

Pasta tasting & cooking classes

Bike tours

Olive oil tours & tastings

Horse riding

Balloon tours

Scooters & motorcycles

Rail tours

Hiking

Vespa tours & rentals

Explore more things to do in Siena

Sightseeing

Food & drinks

Educational activities

Nature & adventure

Driving experiences

Explore more things to do in Siena

Things to do in Florence

Things to do in Pisa

Things to do in San Gimignano

Things to do in Monteriggioni

Things to do in Montepulciano

Things to do in Livorno

Explore more things to do in Siena

Certified by GetYourGuide

From Florence: San Gimignano, Siena, and Chianti Wine Tour

4.455632 out of 5 stars
4.5
4.455632 out of 5 stars
3764 reviews
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Certified by GetYourGuide
From Florence: San Gimignano, Siena, and Chianti Wine Tour
4.455632 out of 5 stars
4.5
4.455632 out of 5 stars
3764 reviews

Discover the enchanting cities of Tuscany on a small-group guided tour. Starting at Piazza del Duomo in Florence, explore Siena, taste wine, enjoy local cuisine, and stroll through San Gimignano.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 9 hours
Check availability to see starting times
Live tour guide
Portuguese, Italian, English, Spanish, Chinese

Highlighted reviews from other travelers

T
Teona – Georgia

The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie

S
Satabdi – Germany

Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information about the last stop. Overall, it was great day, relaxed and every minute of the tour was used. The cherry on top was everybody and everything was on time. Highly recommend this tour.

Select participants and date

Participants

Itinerary

  • Timeline stop icon

    Starting location:

    Regione Toscana - Palazzo Guadagni Strozzi Sacrati

  • Bus/coach

    (110 minutes)

  • Fortezza Medicea

    Walk (15 minutes)

  • Timeline stop icon

    Siena

    Photo stop, Visit, Lunch, Guided tour, Free time, Walk, Self-guided tour (85 minutes)

  • Bus/coach

    (30 minutes)

  • Timeline stop icon

    Winery

    Visit, Wine, Lunch, Free time, Wine tasting, Shopping, Walk, Food tasting (100 minutes)

  • Bus/coach

    (55 minutes)

  • Timeline stop icon

    San Gimignano

    Break time, Visit, Free time, Shopping, Walk, Self-guided tour (80 minutes)

  • Bus/coach

    (1 hour)

  • Arrive back at:

    Regione Toscana - Palazzo Guadagni Strozzi Sacrati

Main stop
Other stop

For reference only. Itineraries are subject to change.

Highlights

  • Escape the bustle of Florence and explore the beautiful Tuscan countryside
  • Visit the medieval town of San Gimignano, home to Vernaccia wine and saffron
  • Explore the immaculate town of Siena, world-renowned for its Palio horse race
  • Visit a splendid Chianti estate and take part in five exclusive wine tastings
  • Savor a traditional Tuscan lunch with cheeses, meats, and Lasagne al Tartufo.

Full description

Start your day by discovering the historical wonders of Siena, one of Tuscany’s most celebrated cities. Famous for its medieval architecture and the renowned Palio horse race, Siena offers plenty to explore, including the iconic Piazza del Campo, the impressive Cathedral of Santa Maria Assunta, and its winding, cobblestone streets full of charm.
Next, you'll be able to walk into the scenic Chianti region to visit a traditional winery. Here, you can enjoy an exclusive guided tour of the vineyard and cellars, followed by a tasting of five types of local wines. Paired with artisanal olive oils, including extra virgin, truffle, and spicy pepper, along with a rich Gold Seal balsamic vinegar, to complement your wine experience.
For lunch, indulge in a traditional Tuscan meal that highlights the region’s finest flavors. Start with an array of appetizers featuring Tuscan cheese, cured meats, bruschetta, and a fresh salad. Savor the first course of Lasagne al Tartufo (truffle lasagna) and the comforting Ribollita, a traditional Tuscan vegetable soup. For dessert, enjoy cantucci cookies paired with Ildebrando Vin Santo, a sweet dessert wine that pairs perfectly with the cookies.
After lunch, head to San Gimignano, a stunning medieval town renowned for its unique skyline of towering medieval structures. As you wander through its UNESCO World Heritage-listed historic center, you can shop for handmade goods in local artisan boutiques and take in breathtaking views of the surrounding countryside.
This full-day Tuscany tour offers a perfect combination of culture, history, delicious wine, and traditional Tuscan cuisine. It’s a truly memorable way to experience the best of Tuscany’s natural beauty, wines, and culinary traditions.
Take your free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets.

Includes

  • Air-conditioned bus or minivan
  • Multilingual guide
  • Free time in Siena
  • Free time in San Gimignano
  • Delicious lunch
  • Wine tastings
  • Guided visit of a Chianti estate
  • Entry to Siena Cathedral
  • Entry to Palazzo Comunale

Not suitable for

  • Wheelchair users

Meeting point

To get to Duomo Square, in front of "Tuscany Region - Guadagni Strozzi Sacrati Palace". Please look for our assistant holding a panel advertising our tour. Upon arriving, look for our staff member(s) wearing either a green t-shirt or a white shirt with a green foulard with a myTour logo. We suggest to be at the meeting point 15 minutes before the starting time

Open in Google Maps

Important information

What to bring

  • Comfortable shoes
  • Credit card
  • Comfortable clothes
  • Cash

Know before you go

  • This tour will be conducted in multiple languages at the same time.
  • The tour itinerary may change according to the season and unforeseen circumstances but all stops will be visited.
  • Customers must be able to climb and descend stairs.
  • Please note that the tour in the Portuguese language is available with a minimum of 4 pax, otherwise will be guaranteed in English.
  • Please note that the tour in the Chinese language is on request and with a minimum of 4 pax, otherwise it will be guaranteed in English.
  • We suggest to be at the meeting point 15 minutes before the starting time.

From $167 per person

Reserve now & pay later to book your spot and pay nothing today
Reserve now & pay later to book your spot and pay nothing today

Customer reviews

Overall rating

4.5 /5

based on 3764 reviews

Review summary

  • Guide
    4.6/5
  • Transportation
    4.7/5
  • Value for money
    4.4/5

Customer photos

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T
Teona – GeorgiaJanuary 26, 2025 – Verified booking
The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie

Response from provider

January 28, 2025

Dear Customer, Thank you for sharing your feedback with us. We're thrilled to hear you had such a great experience with Marco and that you made new friends along the way. We agree, Italy is truly mesmerizing! Not only that, but we also appreciate your lunch recommendation at the winery. Hope to welcome you back on another tour soon. Best regards, My Tour in Italy team.

S
Satabdi – GermanyNovember 9, 2024 – Verified booking
Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information about the last stop. Overall, it was great day, relaxed and every minute of the tour was used. The cherry on top was everybody and everything was on time. Highly recommend this tour.
S
Siddharth – IndiaNovember 7, 2024 – Verified booking
Great trip, Martha was an excellent guide and made the entire trip fun. Definitely recommend this

Product ID: 7679

Activity provider:My Tour in Italy
  • Italy
  • Tuscany
  • Things to do in Siena
  • Tours in Siena
  • Piazza del Campo

Top Attractions in Siena

  • 1Siena Cathedral
  • 2Brolio Castle
  • 3Tower of Mangia, Siena
  • 4Palazzo Pubblico
  • 5Oratory of San Bernardino
  • 6Santa Maria della Scala
  • 7Facciatone
  • 8Cripta del Duomo di Siena
  • 9La Lastra Winery
  • 10Santuario di Santa Caterina
  • 11Museo Civico, Siena
  • 12Baptistery of St John
  • 13Basilica Cateriniana San Domenico
  • 14Piazza del Campo
  • 15Meleto Castle
  • 16Monte dei Paschi di Siena
  • 17Piccolomini Library
  • 18Winery San Giorgio a Lapi
  • 19Fortezza Medicea
  • 20Palazzo delle Papesse

Experiences in Siena

  • 1Siena Wine tasting & winery tours
  • 2Siena Walking tours
  • 3Siena Day trips
  • 4Siena Transfers
  • 5Siena Cooking classes
  • 6Siena Driving experiences
  • 7Siena Churches & cathedrals
  • 8Siena Bike tours
  • 9Siena Food & drinks
  • 10Siena Horse riding
  • 11Siena Entry tickets
  • 12Siena Family-friendly activities
  • 13Siena Castle & palace tours
  • 14Siena Scooters & motorcycles
  • 15Siena Bus & minivan tours
  • 16Siena Balloon tours
  • 17Siena Museums & exhibitions
  • 18Siena Pasta tasting & cooking classes
  • 19Siena Rail tours
  • 20Siena Dinner packages

Tours in Italy

  • 1Rome Tours
  • 2Milan Tours
  • 3Venice Tours
  • 4Florence Tours
  • 5Naples Tours
  • 6Sorrento Tours
  • 7Verona Tours
  • 8Palermo Tours
  • 9Bologna Tours
  • 10Bari Tours
  • 11Como Tours
  • 12Catania Tours
  • 13Genoa Tours
  • 14Taormina Tours
  • 15Turin Tours
  • 16Pisa Tours
  • 17Pompei, Campania Tours
  • 18Cagliari Tours
  • 19La Maddalena Tours
  • 20Olbia Tours

Things to do in Italy

  • 1Things to do in Rome
  • 2Things to do in Milan
  • 3Things to do in Venice
  • 4Things to do in Florence
  • 5Things to do in Naples
  • 6Things to do in Sorrento
  • 7Things to do in Verona
  • 8Things to do in Palermo
  • 9Things to do in Bologna
  • 10Things to do in Bari
  • 11Things to do in Como
  • 12Things to do in Catania
  • 13Things to do in Genoa
  • 14Things to do in Taormina
  • 15Things to do in Turin
  • 16Things to do in Pisa
  • 17Things to do in Pompei, Campania
  • 18Things to do in Cagliari
  • 19Things to do in La Maddalena
  • 20Things to do in Olbia

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Popular Attractions

  • Caminito del Rey
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