Guided Tours

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

Name: From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip
Start: 2026-08-02T07:30:00
End: 2026-08-02T19:00:00
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(2,054)

Pinelopi A

Group

Verified booking

Last week

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.

David N

Couple

Verified booking

Mar 2026

Our guide was Aaron, who was very fluent in several languages and had a special way about him—he was warm and friendly. The experience was truly incredible; I highly recommend it to everyone. Tuscany has hidden treasures that you’ll discover on this tour. I don’t regret taking it. Lunch was excellent, in true Tuscan style, accompanied by a superb wine tasting. I also want to give a shout-out to the drivers, Silvio and Mikel, who did a great job throughout the entire trip.

Ana R

Couple

Verified booking

Feb 2026

I liked all the places we visited, each one was truly wonderful. Even though the weather was terrible, we still enjoyed the destinations. The guide (Ilaria) and the driver (Plácido) were great, super punctual. Maybe a little more time for sightseeing would have been better, but I understand that it would have made the day much longer, and it was already quite intense. As for lunch and the wine tasting at the winery, everything was pretty good, except for the lasagna, which, considering we were in Italy, wasn't what we expected... it tasted like "gas station food." But the rest of the day was fantastic. I would recommend it 100%.

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.

2,054 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
Pinelopi A
Group
Verified booking
Last week
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
3 weeks ago
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.
David N
Couple
Verified booking
Mar 2026
Our guide was Aaron, who was very fluent in several languages and had a special way about him—he was warm and friendly. The experience was truly incredible; I highly recommend it to everyone. Tuscany has hidden treasures that you’ll discover on this tour. I don’t regret taking it. Lunch was excellent, in true Tuscan style, accompanied by a superb wine tasting. I also want to give a shout-out to the drivers, Silvio and Mikel, who did a great job throughout the entire trip.
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

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.