Magpie
4.6(680 reviews)

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
680 reviews
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Tuscany day trip

The overall experience was satisfactory. However, I suggest that our guide, Marina, endeavor to be more energetic and clear in her English delivery, as her accent occasionally presented comprehension difficulties. We noted a more positive experience with previous day trips. Additionally, a cautionary note for elderly participants: this tour involves a significant amount of walking, as bus stops are located at least 300 meters from each destination.

Hardik0231Jul 6, 2026TRIPADVISOR

Nice

The trip was amazing! Marina was so nice and her smile made me feel so safe since I traveled alone.

loow616Jul 6, 2026TRIPADVISOR

3 city

Perfect 🤩 comfortable bus, nice guide!

magdalenarW6639YQJul 6, 2026TRIPADVISOR

Get ready to walk

You should be physically fit for this tour and have plenty of time. At each destination you have 15 minutes of walking to the attraction and an additional 15 walking back to the bus. Skip Pisa if you can. The winery was beautiful and the food was delicious. San Grimigiano (spelling) is a must see with great shopping and amazing views.

Tara KJun 29, 2026TRIPADVISOR

Tour of Pisa , SAN Giminiano, Siena and Chianti

Our tour guide, Marina, was fantastic. She took the time to explain everything thoroughly and always did so with a smile. Our bus driver, Francesco, was an absolute sweetheart—always cheerful, friendly, and incredibly helpful. We had a wonderful day thanks to both of them. I would highly recommend this tour to all my friends and anyone looking for a memorable experience. Your Montreal friends

angelalF9977BFJun 25, 2026TRIPADVISOR

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.
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