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    Explore Siena

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    Siena Cathedral

    Palazzo Pubblico

    Tower of Mangia, Siena

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    Santa Maria della Scala

    Piccolomini Library

    Piazza del Duomo, Siena

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    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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  • 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

Rail tours

Scooters & motorcycles

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

Day trip

From Florence: Tuscany Day Trip with Lunch at Chianti winery

Top rated
4.829412 out of 5 stars
4.8
4.829412 out of 5 stars
4080 reviews
Certified by GetYourGuide
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Day trip
From Florence: Tuscany Day Trip with Lunch at Chianti winery
Certified by GetYourGuide
Top rated
4.829412 out of 5 stars
4.8
4.829412 out of 5 stars
4080 reviews

Discover the vineyards and medieval architecture of Siena, San Gimignano, and Pisa on a small-group or private full-day Chianti journey, with optional lunch and wine.

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 12 hours
Check availability to see starting times
Skip the ticket line
Live tour guide
English

Highlighted reviews from other travelers

K
Katie – United States

don't be turned away by the long time frame - this was an incredible adventure and walk about tours really provided a spectacular time! mano was an amazing guide who was not only knowledgeable but friendly and fun! and I have to agree - san gimignano was my favorite stop, it has my heart! we never would have thought to visited there and Siena so I'm so glad we decided to book this tour. I could not recommend it more and will definitely be using walk about for other tours in the future! please do not pass by this tour you will not regret it! thank you mano for the incredible day!

M
Mitchell – Australia

One of the highlights of our Tuscany trip! The guide was great and gave us so much information throughout the day while also keeping us on time and organised. Seeing the smaller towns was great and the lunch and wine tasting was delicious! Great modern bus for transport as well :)

Select participants and date

Participants

Itinerary

  • Timeline stop icon

    Starting location:

    Firenze S. M. Novella

  • Bus/coach

    (1.5 hours)

  • Timeline stop icon

    Siena

    Guided tour, Free time (1.5 hours)

  • Timeline stop icon

    Chianti Hills

    Lunch (1.5 hours)

  • Timeline stop icon

    San Gimignano

    Free time (1.5 hours)

  • Timeline stop icon

    Pisa

    Free time (1.5 hours)

  • Bus/coach

    (1.5 hours)

  • Arrive back at:

    Firenze S. M. Novella

Main stop

For reference only. Itineraries are subject to change.

Highlights

  • Savor a farmhouse lunch with homemade pasta, cured meats, and local cheeses
  • Explore the splendid squares, churches, and the magnificent towers of San Gimignano
  • See the Leaning Tower of Pisa and other impressive marble monuments in Pisa
  • Choose from either a small-group or private guided experience
  • Admire the beautiful medieval architecture of Siena and its gothic-style Cathedral

Full description

Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day. 

Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour.

Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.  

Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers.

The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence.

Best of all, choose from either a small-group or private guided experience to make your trip special.

Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region.

Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

Includes

  • Expert guide
  • Guided walking tour of Siena
  • Entry ticket to Siena Cathedral
  • Farmhouse lunch at a winery estate in Chianti (if lunch option selected)
  • Wine tasting of 4 regional wines (if lunch option selected)
  • Free time in Siena, San Gimignano, and Pisa
  • Hotel pickup and drop-off
  • Leaning Tower of Pisa entry ticket

Not suitable for

  • People with mobility impairments

Meeting point

The meeting point is in Piazza Stazione. Your guide will be holding a WALKABOUT TOURS sign, right by the taxi stand at Santa Maria Novella train station across from the outside McDonald's.

Open in Google Maps

Important information

What to bring

  • Comfortable shoes

Know before you go

  • If the Siena Cathedral is closed for religious services, the Palazzo delle Papesse will be visited instead
  • Vegetarian option is available, but we regret that gluten free or other alternative dietary requirements cannot be catered for
  • If you are leaving Florence by train after the tour or need to get off at Pisa to catch a flight or train from there, you can bring your luggage with you. It is recommended that you book any rail travel from Florence after 9:00 PM to allow time for any delays on the return journey
Save up to 15%

From $118.80 $100.98 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

4.8 /5

based on 4080 reviews

Review summary

  • Guide
    5/5
  • Transportation
    4.9/5
  • Value for money
    4.8/5

Customer photos

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K
Katie – United StatesMay 6, 2025 – Verified booking
don't be turned away by the long time frame - this was an incredible adventure and walk about tours really provided a spectacular time! mano was an amazing guide who was not only knowledgeable but friendly and fun! and I have to agree - san gimignano was my favorite stop, it has my heart! we never would have thought to visited there and Siena so I'm so glad we decided to book this tour. I could not recommend it more and will definitely be using walk about for other tours in the future! please do not pass by this tour you will not regret it! thank you mano for the incredible day!
M
Mitchell – AustraliaMay 5, 2025 – Verified booking
One of the highlights of our Tuscany trip! The guide was great and gave us so much information throughout the day while also keeping us on time and organised. Seeing the smaller towns was great and the lunch and wine tasting was delicious! Great modern bus for transport as well :)
O
Olivia – United KingdomMay 4, 2025 – Verified booking
John Luca was an excellent guide, the coach was extremely comfortable for the long day of travelling. Definitely select the lunch option, simple delicious food in a beautiful setting. A long tiring day but worth it.

Product ID: 383686

Activity provider:Walkabout Tours
  • Italy
  • Tuscany
  • Things to do in Siena
  • Tours in Siena
  • Siena Cathedral

Top Attractions in Siena

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

Experiences in Siena

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

Tours in Italy

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

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Popular Attractions

  • Moulin Rouge
  • Caminito del Rey
  • Sagrada Familia
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  • Louvre Museum
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  • Italy
  • Tuscany
  • Things to do in Siena
  • Tours in Siena
  • Siena Cathedral
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