Tuscany Day Trip: Pisa, Siena, San Gimignano & Wine Tasting

From€52
12 hours
Florence, Italy

About this activity

Experience the best of Tuscany in a single day with visits to Pisa, Siena, and San Gimignano, complemented by a delightful wine tasting in the Chianti region.

Highlights

  • Marvel at Pisa's Leaning Tower
  • Explore Siena's historic center
  • Wander through San Gimignano's medieval streets
  • Enjoy a scenic drive through Chianti vineyards
  • Savor local wines during a guided tasting

Full description

Discover the enchanting landscapes and rich history of Tuscany on this immersive day trip from Florence. Begin with a visit to Pisa, where you'll marvel at the iconic Leaning Tower and the surrounding architectural wonders. Next, explore the medieval streets of Siena, renowned for its stunning cathedral and the historic Piazza del Campo. Continue to San Gimignano, often referred to as the 'Town of Fine Towers,' and wander through its charming alleys lined with ancient stone buildings. Throughout the journey, enjoy a scenic drive through the picturesque Chianti region, famous for its rolling hills and vineyards. The tour includes a guided wine tasting, allowing you to savor the region's renowned Chianti wines. This excursion offers a perfect blend of art, history, and gastronomy, providing an unforgettable Tuscan experience in just one day.

Included / Excluded

  • Guided tour of Pisa, Siena, and San Gimignano
  • Wine tasting in the Chianti region
  • Transportation from Florence in an air-conditioned vehicle
  • Meals and beverages not specified in the itinerary

Itinerary

1

Pass by: Tour leaves from Florence city centre in the early morning , to reach Pisa San Gimignano and Siena

Admission: NOT_APPLICABLE
2

Your day starts in the morning with a free tour of Pisa, where you will have time to admire the magnificent cathedral, the baptistery, the monumental cemetery and the famous Leaning tower of Pisa.

Duration: 2 hoursAdmission: NOT_APPLICABLE
3

If selected you have the chance to climb this iconical tower, known for its nearly four-degree lean, the result of an unstable foundation.

Duration: 40 minAdmission: NO
4

Pass by: Enter the oldest of the three structures in the plaza followed by the Pisa Baptistry and the Leaning Tower.

Admission: NOT_APPLICABLE
5

Pass by: Look at Monumental Cemetery, where the legend claims that bodies buried in that ground will rot in just 24 hour.

Admission: NOT_APPLICABLE
6

Pass by: Fall in love with Pisa and the amazing Piazza Dei Miracoli: the most popular attraction in Pisa where you will have free time to visit the Leaning Tower, the Cathedral and the Baptistery or realaxing In the green meadow under the shadow of one of this monument. You can also choose the option that includes Leaning Tower Entrance

Admission: NOT_APPLICABLE
7

Pass by: Admire the largest baptistery in Italy, it is 54 m high, with a diameter of 34, built from 1152 to 1363

Admission: NOT_APPLICABLE
8

While heading to the wine estate, enjoy the breathtaking Chianti scenery. Afterwards, you will be comfortably driven to a rustic winery in Chianti, on the slopes of San Gimignano, where you will be invited to a delightful wine tasting enriched with some local culinary specialties, such as bruschettas, pecorino cheese and a variety of cold cuts.

Duration: 1h 20mAdmission: YES
9

After lunch you discover, San Gimignano: the Medieval Manhanattan, where you can explore the maze of cobbled streets, small squares and many local craft stores.

Duration: 1 hourAdmission: NOT_APPLICABLE
10

Pass by: Piazza del Duomo in San Gimignano was the fulcrum of the religious and political life of the town in the Middle Ages. The square owes its name to the Collegiate Church, which has been there since the 11th century, while the current appearance of the square took shape in the first half of the 13th century, during the golden period of the economy and political importance of San Gimignano . The main public buildings and the "rotation" of the cathedral date back to that period, with a new facade opposite the old Palazzo del Podestà. Today the square is slightly sloping and has a brick pavement.

Admission: NOT_APPLICABLE
11

Pass by: Piazza della Cisterna is, with the Piazza del Duomo, one of the two most important squares in San Gimignano. The square has a triangular shape with a slight natural slope and is connected to the nearby Piazza del Duomo by an open passage. The pavement is herringbone brick and on the sides there is an extraordinary curtain of noble houses and medieval towers.

Admission: NOT_APPLICABLE
12

Our exciting day continues with a panoramic view of the true Chianti countryside before arriving in Siena, where our professional guide ( if option selected ) will let you discover the most important squares, from Piazza del Campo to the Cathedral passing through the most beautiful ‘Contrade’ that characterize this city. At the end of the guided tour, you will have free time to enjoy a cup of coffee or the Pan Forte (the typical local cake) and have some shopping in typical local shops.

Duration: 1h 30mAdmission: NOT_APPLICABLE
13

Pass by: Piazza del Campo (or more simply the Campo) is the main square of the city of Siena. Unique for its particular and very original shell shape, it is renowned throughout the world for its beauty and architectural integrity, as well as for being the place where the Palio di Siena takes place twice a year.

Admission: NOT_APPLICABLE
14

Pass by: The cathedral of Siena, officially the metropolitan cathedral of Santa Maria Assunta, is the main place of Catholic worship in Siena, in Tuscany, the episcopal seat of the metropolitan archdiocese of Siena-Colle di Val d'Elsa-Montalcino; the building is located in the square of the same name, in Terzo di Città. Built in Italian Romanesque-Gothic style, it is one of the most significant churches built in this style in Italy.

Admission: NOT_APPLICABLE
15

Pass by: Come back in the evening at the same point in the city center

Admission: NOT_APPLICABLE

Meeting point

Start Location

Unknown location

Important information

Know before you book

  • The tour operates in English; ensure you understand the language for a full experience.
  • Confirm the departure time and location in advance to avoid any confusion.
  • Be aware that the itinerary may involve walking on uneven surfaces; consider your comfort and mobility.

Know before you go

  • Wear comfortable walking shoes suitable for cobblestone streets.
  • Bring a camera to capture the stunning landscapes and historic sites.
  • Check the weather forecast and dress accordingly for the day's conditions.

Cancellation policy

Free cancellation up to 1 days before the activity starts

For a full refund, cancel at least 24 hours before the scheduled departure time.

Accessibility

  • Stroller Accessible
  • Easy Public Transport
  • Infants Required On Laps

Good to know

  • The order of visits may change.
  • In order to reserve a seat even for children under 4 years of age, it is necessary to select the free rate "children (0-3)" during the purchase phase.
  • Possibility to have a dedicated menu for vegetarians or people with intolerances. We kindly ask you to promptly notify us of any special dietary requirements or intolerances once the purchase the tour by sending an e-mail.
  • Meeting point at Sightseeing Experience Visitor Center inside Train Station Santa Maria Novella
  • Pisa tower: entry is not allowed for children under the age of 8 (completed or to be completed in the current year)
  • No refunds are given in case of delay at the meeting point at Sightseeing Experience Visitor Center
  • Maximum punctuality is recommended at each meeting points during the excursion. For the success of the tour, no waiting times are expected in case of delays by ustomers and no refunds will be granted
  • The order of visits may change
  • Transfer Only option includes only bus and assistance on board.
  • Travelers cannot book options with "+ Tower" if they have a child, due to Pisa Tower restrictions that prohibit children under 8 years old from entering.

Traveler reviews

4.6
664 reviews
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509
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12

Must to See Tuscan side in one day!

Our tour was with Barbara and she was very informative and inclusive in all aspects. Barbara arranged accommodations as needed. Overall tour was great to be able to see the Tuscan side in one full day, although about 1-2 hours were spent in each location and the rest was travel but that is something to expect coming from Florence. I would definitely do this tour again! Be prepared to walk 20k steps.

miream_cMay 22, 2026VIATOR

Can't Miss Tuscany, but Wish for Better Hospitality

READ BOTTOM 3 PARAGRAPHS FOR TIPS ON PISA & SAN GIMIGNANO. 10 years ago, I did almost an identical tour. It feels as though the service industry as a whole has declined. You pay more for less. While our tour guide was great, my main complaint is that I had expected an English tour and it was bilingual because there were 4 Spanish speakers. This drastically limited how much our tour guide could share because she had to repeat everything in a 2nd language. And while her English was perfectly fine, she did have an accent, so sometimes I thought she was still doing the Spanish translation, but realized she had switched back to English and I missed information because I had tuned out during the Spanish. Secondly, when we came 10 years ago, we got an amazing tour of the winery and farm, a 3-course lunch with dessert and extra wine, and very personal attention from the winery hosts for at least 90 minutes, if not 2 hours. This time, you get 1 hour, there's SO many people (2 groups crammed together, and our group alone had 34 people which was apparently "small"), no tour of the winery, and almost no communication from the hosts. While the winery is beautiful and the views spectacular, there is just no hospitality, and the food left much to be desired--mostly bread, cheese, and sliced meats. No dessert, only 3 small tastings of wine. Some people at our table had the "vegetarian" option which I almost wish I picked because it was a full plate of balsamic parmesan squash which looked delicious. In San Gimignano, last time our tour guide showed us the best view, this time we had to Google it--"Parco della Rocca"-- TIP: make sure to keep walking because the view gets better. You won't have any time for shopping, so consider staying a couple days in a nearby hotel to truly appreciate it. This is what we did so we missed the Siena portion of the tour. As for Pisa, make sure you get the free Cathedral ticket right away, because we didn't realize it was timed entry, so we got the ticket with 30 minutes left, and the timed entry was for an hour after we left so we couldn't enter. However, I highly recommend taking the 10-minute walk to "Caffè Antiche Terme". Perhaps our best cafe experience in Italy so far. Lastly, the tour guide and bus driver were very accommodating as we brought our suitcases to put underneath so we could get off at San Gimignano for our hotel. While I sound negative in the review, the locations are still so amazing that it's worth doing the tour and I gave it 4 stars. You can't miss seeing the beauty of Tuscany.

837zachtMay 10, 2026TRIPADVISOR

Siena, San Gimignano, Pisa tour

This is a great tour. The tour guide was very knowledgable in the locations visited and the towns we drove by. The wine tasting was fun but the food was pretty average. Timing for everything went smoothly. We would have liked a bit more time in Siena and less time in Pisa but all in all was an excellent tour and well worth the money.

Ryan_BApr 10, 2026VIATOR

Wonderful day out

Great tour and stress free, Barbara and the team looked after us throughout the trip. Very informative and not an over load of information. Wine tasting and lunch was wonderful with great views. Had a wonderful day seeing all three sights.

Sonia_DApr 7, 2026VIATOR

The worst! Do not use this operator!

At one in the morning on a Friday, I thought I was booking the tour for Sunday. Immediately upon booking, I realized that I booked it for the same day, six hours later. I immediately called Viator got them on the phone, and emailed and texted the tour operator explaining that it was the wrong date and please change it to Sunday. I tour said they could do nothing because it was the same date, but that first thing in the morning I would hear from them because they were closed. The tour company reached out to me after 9 AM, when the tour was meeting at 7 AM,. They said “ we can’t change the date, and ,no refund will be given.” !!!! I wasted over $200 in a matter of minutes. An honest mistake, which I realized immediately. Horrible operator! Never again would I book anything with them. They were so robotic and unsympathetic and uninterested in helping me. Ignored my text and my follow up email. we were so disappointed. Do not book with them! And shame on Viator for not doing anything either. I have booked so many tours with them.

Jenine_SMar 27, 2026VIATOR

Additional information

The order of visits may change. In order to reserve a seat even for children under 4 years of age, it is necessary to select the free rate "children (0-3)" during the purchase phase. Possibility to have a dedicated menu for vegetarians or people with intolerances. We kindly ask you to promptly notify us of any special dietary requirements or intolerances once the purchase the tour by sending an e-mail. Meeting point at Sightseeing Experience Visitor Center inside Train Station Santa Maria Novella Pisa tower: entry is not allowed for children under the age of 8 (completed or to be completed in the current year) No refunds are given in case of delay at the meeting point at Sightseeing Experience Visitor Center Maximum punctuality is recommended at each meeting points during the excursion. For the success of the tour, no waiting times are expected in case of delays by ustomers and no refunds will be granted The order of visits may change Transfer Only option includes only GT bus and assistance on board. Travelers cannot book options with "+ Tower" if they have a child, due to Pisa Tower restrictions that prohibit children under 8 years old from entering.