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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

Olive oil tours & tastings

Bike tours

Horse riding

Balloon tours

Rail tours

Scooters & motorcycles

City cards

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: Tuscany Day Trip with Lunch at Chianti winery

Top rated
4.8 out of 5 stars
4.8
4191 reviews
Activity provider:
Walkabout Tours
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Certified by GetYourGuide
From Florence: Tuscany Day Trip with Lunch at Chianti winery
Top rated
4.8 out of 5 stars
4.8
4191 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

5
5 out of 5 stars
D
Deirdre – New Zealand

Fabulous very full day in Tuscany. Our guide Gabriel was excellent, communication was spot on, gave us great information about the tour, and our driver Domenico got us to all the places and back with skill! Loved Siena and San Gimignano and of course Pisa. Lunch was delicious in a beautiful Tuscan setting.

5
5 out of 5 stars
M
Marianne – United Kingdom

David and Francesco were amazing, the trip was excellent!

Select participants and date

Participants

Itinerary

  • Starting location:

    Firenze S. M. Novella

  • Bus/coach

    (1.5 hours)

  • Siena

    Guided tour, Free time (1.5 hours)

  • Chianti Hills

    Lunch (1.5 hours)

  • San Gimignano

    Free time (1.5 hours)

  • 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 20%

From $123 $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
4.8 out of 5 stars

based on 4191 reviews

Review summary

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

Customer photos

+476
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5
5 out of 5 stars
D
Deirdre – New ZealandJuly 9, 2025 – Verified booking
Fabulous very full day in Tuscany. Our guide Gabriel was excellent, communication was spot on, gave us great information about the tour, and our driver Domenico got us to all the places and back with skill! Loved Siena and San Gimignano and of course Pisa. Lunch was delicious in a beautiful Tuscan setting.
5
5 out of 5 stars
M
Marianne – United KingdomJuly 7, 2025 – Verified booking
David and Francesco were amazing, the trip was excellent!
5
5 out of 5 stars
F
Francesco – CanadaJuly 2, 2025 – Verified booking
Unbelievable day, perfect to get a taste of the Tuscan valley cities. Bus has A/C and super comfortable for the in between rides. Siena, San Gimignano and Pisa were beautiful sites to see and the winery for lunch and wine tasting was a must do. Our bus driver Emiliano and tour guides Gabrielle and Manolo were excellent. Definitely recommend this trip.

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

Experiences in Siena

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

Tours in Italy

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  • 3Venice Tours
  • 4Florence Tours
  • 5Naples Tours
  • 6La Maddalena Tours
  • 7Sorrento Tours
  • 8Palermo Tours
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  • 11Como Tours
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  • 13Genoa Tours
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  • 17Pompei, Campania Tours
  • 18Cala Gonone Tours
  • 19Taormina Tours
  • 20Polignano a Mare Tours

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  • 3Things to do in Venice
  • 4Things to do in Florence
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  • 8Things to do in Palermo
  • 9Things to do in Verona
  • 10Things to do in Bari
  • 11Things to do in Como
  • 12Things to do in Bologna
  • 13Things to do in Genoa
  • 14Things to do in Catania
  • 15Things to do in Cagliari
  • 16Things to do in Olbia
  • 17Things to do in Pompei, Campania
  • 18Things to do in Cala Gonone
  • 19Things to do in Taormina
  • 20Things to do in Polignano a Mare

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