Guided Tours

From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip

Name: From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip
Start: 2026-10-02T07:30:00
End: 2026-10-02T19:00:00
Location: Florence

On a guided tour from Florence, visit the World Heritage sites of San Gimignano, Pisa, one of the 7 world wonders, and Siena.

4.5/5(2,059)

Viviana M

Couple

Verified booking

Last week

Booking a last-minute day tour to Siena, San Gimignano, and Pisa can be risky, but this experience exceeded all expectations. The entire itinerary matched the app’s description perfectly, leaving zero room for confusion or unexpected hiccups along the way. The app itself made navigating the schedule, meeting points, and tour details effortless. Compared to other travel platforms I’ve used in the past, it provides far better organization and unbeatable value for money

Pinelopi A

Group

Verified booking

Jul 2026

Although we lost half of the trip because we could not find the meeting point we managed to find our group and live the experience at sienna ! The girls at the meeting point were very polite and helped me book train tickets to find the other people of my group. Barbara was super guide and kind! Thanks also rachel from headout chat who gave me some credits for another trip. I am grateful.

Fabrizio T

Solo

Verified booking

Jun 2026

An exciting experience. Highly recommended and impeccably organized from start to finish. One of the highlights was Sandro, our guide. Professional, empathetic, engaging, and tireless. You can tell he loves his job. Lucky him—and lucky are those who get to work with him. I’d also put Adele, the guide who welcomed us in Siena, on the same level. Professional, engaging, empathetic, and special. She makes you want to return to Siena tomorrow to discover the countless things this Tuscan gem has yet to reveal to a fly-by visitor—things that she, as a true Sienese, surely knows.

Rubén A

Group

Verified booking

Mar 2026

It was a truly wonderful tour. Our driver, Daniel, was a true professional, and our guide, Constantino, was very friendly and made the tour enjoyable by providing us with useful information throughout. A day to remember

Adriana V

Couple

Verified booking

Mar 2026

I really liked how easy it was to get there. I didn't like the amount of time allotted for lunch. Eating lasagna and tasting wines in just an hour was terrible. I suggest simply spacing things out better.

Discover the Tuscan experience with its lyrical landscapes and edgy world-class art, with a guide in the language of your choice!

Visit the walled hill city of Siena, known for its medieval appeal and Gothic appearance. Check out the Piazza del Campo, known famously to hold the Palio Horse Race every year.

Explore the World Heritage Site of San Gimignano, an eternally sought-after destination with its skyline of medieval towers.

Discover Pisa and its renowned charm with places like Piazza dei Miracoli, and the famous Leaning Tower.

Enjoy a delicious Tuscan lunch with a local wine-tasting tour amidst the rolling hills in the Chianti region.

Full-day tour of Tuscany, Siena, San Gimignano and Pisa

Expert English, Spanish, Italian, Portuguese, or French-speaking guide

Round-trip transfers from Florence by coach

Typical Tuscan lunch with drinks (optional)

Wine tasting (optional)

Entry to Leaning Tower of Pisa

Entry to Siena Cathedral

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

2,059 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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What our guests say
Viviana M
Couple
Verified booking
Last week
Booking a last-minute day tour to Siena, San Gimignano, and Pisa can be risky, but this experience exceeded all expectations. The entire itinerary matched the app’s description perfectly, leaving zero room for confusion or unexpected hiccups along the way. The app itself made navigating the schedule, meeting points, and tour details effortless. Compared to other travel platforms I’ve used in the past, it provides far better organization and unbeatable value for money
Mihociu C
Group
Verified booking
Last week
That there was something for everyone, a good route, and the schedule was respected.
Pinelopi A
Group
Verified booking
Jul 2026
Although we lost half of the trip because we could not find the meeting point we managed to find our group and live the experience at sienna ! The girls at the meeting point were very polite and helped me book train tickets to find the other people of my group. Barbara was super guide and kind! Thanks also rachel from headout chat who gave me some credits for another trip. I am grateful.
Hartmut P
Couple
Verified booking
Jul 2026
I enjoyed the variety of this tour. The information provided by the tour guide was very inadequate. We would have liked to learn more about the places we visited.
Fabrizio T
Solo
Verified booking
Jun 2026
An exciting experience. Highly recommended and impeccably organized from start to finish. One of the highlights was Sandro, our guide. Professional, empathetic, engaging, and tireless. You can tell he loves his job. Lucky him—and lucky are those who get to work with him. I’d also put Adele, the guide who welcomed us in Siena, on the same level. Professional, engaging, empathetic, and special. She makes you want to return to Siena tomorrow to discover the countless things this Tuscan gem has yet to reveal to a fly-by visitor—things that she, as a true Sienese, surely knows.

Kickstart the tour with Siena and some authentic wine tasting

As Italy’s most-frequented province, there is little doubt that Siena is amongst the country’s most beautiful locations. Located in the Tuscany region, Siena is known primarily for its diverse range of historical monuments from the medieval period. The landscape is dotted with Romanesque and Gothic monuments. Your tour begins here, with a visit to Piazza del Campo where the famous Palio Horse Race is held twice annually, following the Piazza del Duomo, where you can soak in the stunning exterior of the magnificent Cathedral. After whiling away time doing your own thing, you will head to a winery located in between Siena and San Gimignano. Here, you will indulge in an authentic wine tasting experience with addition to a delectable Tuscan menu for lunch. The lunch consists of Bruschetta for starters, salami and fresh cheese, as first course tagliatelle with ragù sauce (upon request with tomato) and a typical dessert (wine and water included) to end the meal.

Experience the medieval atmosphere of San Gimignano

San Gimignano, famously known as the Town of Fine Towers, is your next attraction on the itinerary. With numerous churches like the Collegiate Church and the Church of Sant'agostino, this gorgeous walled town embodies the true essence of medieval Europe. Here, you can make the most of your free time with a visit to Piazza della Cisterna and Piazza del Duomo. Try out the world famous Gelato and capture stunning photos that will remain in your mind’s eye for years to come.

Discover the best attractions in Pisa

After San Gimignano, you will follow the picturesque roads rolling down the Chianti region to the compelling city of Pisa. Discover the treasures hidden within Piazza dei Miracoli, from the Baptistery to the Leaning Tower of Pisa. The Leaning Tower, constructed in the 12th and 13th centuries is one of the most notable landmarks in Europe and one of the seven wonders of the world. It stands at a height of 56 meters, and leans at almost 4 degrees, which led to its now famous name. After spending some free time here, your tour will come to an end. Head back to Florence with a boat load of memories that will last you a lifetime.

Accessibility

This tour is not wheelchair accessible.

Additional information

For lunch, a vegetarian menu is available on request. Dietary requirements should be specified at the time of booking.

Customers must be able to climb and descend stairs. Please note that a moderate amount of walking is involved.

The order of your visit may change.

Note: Seine refers to the town and not the Cathedral.

Reach at the meeting point 15 minutes early to avoid cancellation due to delays. In such cases, refunds will not be granted.

Your voucher will be emailed to you instantly.

Please display the voucher on your mobile phone 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. Students must show their valid student IDs.

Meeting point

Please check your final voucher for the meeting point details and specific instructions.