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Day Trips

Day Tour of Siena, San Gimignano, Chianti & Pisa with Lunch

day tour of siena, san gimignano, chianti & pisa with lunch-2

Experience the charm of Tuscany as you embark on a journey through its enchanting landscapes and iconic spots, traversing the Chianti countryside.


  • Set out on a journey to explore the most renowned Tuscan towns in just one day and take photographs of the lovely farmhouses and olive groves.

  • Discover the captivating highlights of Siena, a city renowned for its enchanting narrow medieval streets, and charming squares.

  • Enjoy a guided tour of the magnificent Siena Cathedral, accompanied by an expert guide, and dig into delicious Tuscan lunch with wine pairing.

  • Explore the UNESCO World Heritage Site of San Gimignano, as well as Pisa, famous for its amazing Leaning Tower.

  • Did you know? San Gimignano is the "World Capital of Gelato," and houses several renowned gelaterias, offering a variety of delicious flavors.


  • Staff assistance at the meeting point

  • Transport by air-conditioned coach with Wi-Fi onboard

  • Licensed tour leader (English or Spanish)

  • 3-course traditional Tuscan lunch with wine pairing

  • Siena local guide (optional)

  • Siena Cathedral entrance fee (optional)

Cancellation policy

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.


1.9K reviews
  • United States
  • India
  • Australia
  • Austria
  • Spain
  • Puerto Rico
  • United States
  • India
  • Australia
  • Austria
  • Spain
  • Puerto Rico
Guests from United States, India, Australia and over 6 countries have loved this experience
Prachi Jain



Jan, 2024

Hi, My experience with Headout team and the guide was suoer amazing, I think on our own we wouldn't have ever visited so many places in one day, but due to this trip we could visit so much and the guide was also very informative. I speacially love the wine tasting experience. Wish we would have got more time everywhere but it was a little hectic but worth visting ..I just loved it.
carolin gostner



Mar, 2024

The tour guide Elisabetha and the bus driver Alexander were very good!
View original review in German
Maura Lynch



Jan, 2024

These were beautiful areas in Tuscany to visit, and the logistics support was helpful. Guide was friendly.
Aythami Fernández López



Dec, 2023

Madeline Betancourt



Nov, 2023

Embark on your Tuscany adventure starting with the iconic city of Pisa. As you step off the coach, be greeted by the mesmerizing Field of Miracles—a vibrant green expanse adorned with the dazzling white structures of the Cathedral, the Baptistery, and the world-famous Leaning Tower. Immerse yourself in this renowned location, snap creative photos, or lose yourself in the charm of local streets.

Onto Medieval Discoveries

From Pisa, you drive past hilltop hamlets scattered over some of the most beautiful and enchanting views of the countryside to arrive at San Gimignano where a traditional Tuscan Lunch with wine pairing, (if the option is selected) will be served. After lunch, venture into the enchanting realm of San Gimignano, a Tuscan medieval gem and UNESCO World Heritage site. Revered for its ancient town planning still intact, it's often nicknamed the 'Manhattan of the Middle Ages' due to its iconic tall towers, creating a skyline reminiscent of a modern city. Here you have free time to explore the town center, the charming craftsmen’s shops along the cobbled stone streets, and small squares.

The final destination is Siena, accessible via a scenic drive through the captivating Chianti countryside. Siena, a breathtaking hilltop town, boasts a wealth of art, traditions, and picturesque views. Traverse its pedestrianized historical center on a guided walking tour led by a local expert. Marvel at the oldest bank in the world, stroll through the historic Piazza del Campo, and culminate your journey at the awe-inspiring Cathedral. This visit marks the conclusion of your unforgettable Tuscan experience, leaving you with memories of a perfect day.

What to bring

  • It's recommended to wear comfortable walking shoes, and appropriate clothing to visit places of worship.

  • Appropriate clothing is recommended to visit places of worship.

Additional information

  • Please note that the order of visits may change.

  • For groups of up to 8 people, the tour's escort service could be replaced with an English-speaking driver-guide service, while maintaining unchanged the entire program of the excursion.

  • From Nov to Mar, the guided walking tour in Siena is available in both English and Spanish.

  • From Apr to Oct, the guided walking tour in Siena will be monolingual and will be available in English or Spanish, depending on the option selected.

  • Your voucher will be emailed to you instantly.

  • Please display your mobile voucher along with a valid photo ID at the meeting point.

  • If you have purchased reduced-price tickets, please carry your valid photo ID proof for verification.

  • Kindly ensure that you arrive 10-15 minutes before the start time of your tour to avoid any delays.

Meeting Point

  • Meet your tour guide at Piazzale Montelungo, At the end of the ramp connecting to the railway station.

An assistant will wait for you wearing blue clothing with Caf and Gray Line logos.

Get Directions to the Meeting Point

Getting There

  • The nearest train station is Santa Maria Novella Station, It is a 8-minute walk to the meeting point. Board trains EN, FR, FA and IC to get you there.
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