Day trip

From Florence: Tuscany Day Trip with Lunch at Chianti winery

Activity provider: Walkabout Tours
Day trip

From Florence: Tuscany Day Trip with Lunch at Chianti winery

Activity provider: Walkabout Tours
Likely to sell out

From US$ 80.14 per person

Likely to sell out

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


9 hours
  • Florence

  • 1.5 hours
  • Siena (guided tour, free time)

  • Chianti Hills (lunch)

  • San Gimignano (free time)

  • Pisa (free time)

  • 1.5 hours
  • Florence

Meeting point
Main stop
  • 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.
  • 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

Select participants and date



Meeting point

• Meet in front of the Santa Maria Novella train station by the taxi stand, which is located right across the street from the McDonald's outside the station

Open in Google Maps ⟶
Important information

What to bring

  • Comfortable shoes

Know before you go

  • Shared group and private options do not always offer the same languages. Please check all languages of interest to find your preferred option type
  • If the Siena Cathedral is closed for religious services, the Santa Maria della Scala Museum will be visited instead
  • 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
Customer reviews

Overall rating

4.9 /5

based on 1965 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Service

Sort by:

Traveler type:

Star rating:

Sara, our tour leader, is very kind, funny and gives the best tips to enjoy the time we have in each place in the best way. The three cities are just amazing, each one in it’s special way. The lunch was very good, served with great wine of four kinds, all produced by the house, as well as the olive oil. This is a nice way to get the best out of Tuscany in one day, of course you could enjoy more each place with more time, however Sara’s guidance really help those with a tight schedule. We should thank Emiliano for the gentle drive through the curves of Tuscany, taking us safely and smoothly in our journey.

Read more

March 16, 2023

We had an amazing day. breathtaking views, the food and wine were delicious, but most of all, our tour guide Manolo was the best we could have in every way: the tour guide in Siena (Annalisa) was also great, both were very informative, entertaining and fun. we really felt the passion and love for what they do. we felt very well taken care of by the entire team. Thanks for making this experience unforgettable for us.

Read more

March 16, 2023

This was such an enjoyable day trip. The views, food and guide were all exceptional. There was plentiful of wine to go with each course, so definitely felt it was good value. Our guide, Alex, was hilarious and knowledgeable. Cathedrals close on Sundays to tours, so sadly, we didn’t get to go inside the Siena cathedral. Instead, we went to the hospital museum. If visiting the church is important to you, don’t make the same mistake and book it on another day.

Read more

March 14, 2023

Product ID: 383686