Day trip

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Activity provider: CAF Tour & Travel

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Activity provider: CAF Tour & Travel
Likely to sell out

From US$ 65.67 per person

Likely to sell out

Discover the wonders of the Italian countryside on this full day tour through the heart of Tuscany.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details. Learn more
Duration 11 hours
Check availability to see starting times.
Live tour guide
Spanish, English, French

Experience

Itinerary
7.5 hours
  • Florence

  • 1.1 hours
  • San Gimignano (free time)

  • 30 minutes
  • Monteriggioni (free time)

  • 10 minutes
  • Chianti Hills (lunch, winery)

  • 30 minutes
  • Siena (guided tour, free time)

  • 1.15 hours
  • Florence

Meeting point
Main stop
Highlights
  • Visit two UNESCO World Heritage sites
  • Tour the beautiful Siena Cathedral, led by a local guide
  • Enjoy wonderful views of Tuscan rolling hills and Chianti countryside
  • Stop at a Chianti winery for lunch and a guided tasting of three different wines
Full description

Along the way that will lead you to Siena, stop at San Gimignano, a small and world-famous walled town located on a hilltop, which remained intact through the centuries. It is renowned for its tall towers, wonderful frescoes and many other valuable works of art. 

Here, be led to the heart of the historical center, where you will have free time to explore. Following San Gimignano, stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day. 

Enjoy some free time to visit this village. Then, crossing the gently rolling Chianti hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies.

Upon arrival in Siena, after free time for lunch, meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo. 

Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town.

The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race. 

The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public. 

If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.

Includes
  • Transportation by air-conditioned bus
  • Multilingual tour escort on board
  • Professional local guide in Siena
  • Museum entrance fees
  • Wine tasting
  • Lunch
  • Siena Cathedral guided visit with entrance ticket (if option selected)
  • Hotel pickup and drop-off
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask
  • All participants who are over 12 years old must present proof of full vaccination
  • All participants are required to bring and wear FFP2 masks. Blue surgical masks will not be accepted

Select participants and date

Participants

Date

Meeting point

Piazzale Montelungo (Montelungo Square), at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with the local partner's logo.

Open in Google Maps ⟶
Important information

What to bring

  • Comfortable shoes

Know before you go

  • The escort service is provided by professional multilingual tour leader
  • The local guide service could be provided in two languages
  • Please note that the order of the visits may change
  • If the tour or the language cannot be confirmed, you will be offered an alternative or a full refund
  • For small groups of up to 8 people, the tour guide service could be replaced with an English-speaking driver-guide service, with the rest of the program remaining unchanged.
Customer reviews

Overall rating

4.3 /5

based on 144 reviews

Review summary

  • Guide
    4.4/5
  • Transportation
    4.6/5
  • Value for money
    4.3/5
  • Safety
    4.5/5

Sort by:

Traveler type:

Star rating:

We liked it, it was an excursion with Spanish speakers and English speakers, the guide defended himself very well in both, finding out how he could explain the places in both languages as we passed, although he spent more time in English. Upon arrival in Siena we had a guide only for Spanish speakers, the interior of the Siena Cathedral was impressive. We had a good time.

Read more

September 19, 2022

Was so well run and organised.. Felt completely looked after for the whole tour.. Fantastic to see so much in a day.. we never would have done it on our own.. the only one improvement we could suggest would be a clearer meet up point as the rep was surrounded by people so you couldn’t identify her or where you had to go.. a sign held up over her head or something would have been great..

Read more

September 13, 2022

The guides were very good, the bus was good, the lunch was good. On the bus, couples end up being split do to single people not being considerate. Not sure how you can address this, but possibly you could be aware and make announcement to suggest single people be considerate of families and couples. The AC was not working well enough as most of the ride was very hot.

Read more

September 7, 2022

Product ID: 4511