Tours/Florence/Premium Private Tour to Siena, Pisa, San Gimignano and Tuscany
Viator · Private tour

Premium Private Tour to Siena, Pisa, San Gimignano and Tuscany

4.8(149)Florence1 hour
VIATOR4.7(63)TRIPADVISOR4.9(86)

Description

Experience a full-day, private tour of the Tuscan gems, Pisa, Siena, and San Gimignano. Let your private driver do all the paperwork and explore Siena, Pisa and San Gimignano at your own pace. With hotel pickup and drop-off from Florence, you will be able to sit back and enjoy the picture postcard Tuscan countryside surrounding you and your travel companions. Make the most out of this private experience with a private and knowledgeable driver at your full disposal. Design with him the itinerary of your dreams!

Tour Options

English and Leaning Tower
  • Leaning Tower Ticket: Make your experience more exciting by adding skip-the-line tickets to the Leaning Tower of Pisa Pickup included
Private tour in English
  • Pickup included
Spanish and Leaning Tower
  • Leaning Tower Tickets: Make your experience more exciting by adding skip-the-line tickets to the Leaning Tower Pickup included
Private tour in Spanish
  • Pickup included

Itinerary

60 min

Begin your journey through the heart of Tuscany in absolute comfort… A private driver will pick you up directly from your accommodation in a luxury Mercedes vehicle. Then, you will be on your way, driving through the spellbinding scenery of Tuscany with its vibrant greenery, hilltop towns, and countless vineyards. You will arrive in Siena in about an hour.

120 min

Your driver will drop you off very close to the Siena Cathedral, a major perk of arriving in a private vehicle! Siena is a hidden gem of medieval glory in the Tuscany region. With a rich history of architecture, art, and culture, Siena itself is a UNESCO World Heritage Site. Enjoy two hours of exploration throughout the beautiful buildings, artisanal shops, award winning restaurants, and picturesque alleyways.

60 min

While discovering Siena, you will inevitably find your way to the most famous square in the city - Piazza del Campo. Not only is this piazza a popular place for locals to gather, but it is also home to an annual palio horse race, which is an epic competition between the different neighborhoods of Siena! After admiring the panoramic views of this large, shell shaped square, you will have free time to grab a cappuccino at one of the many cafes lining Piazza del Campo, experiencing Siena as the locals do.

30 min

Rising above Piazza del Campo, you can find Torre del Mangia, the intriguing clock tower of Siena. This incredible tower dominates the city's skyline and is the third tallest tower in all of Italy! Interestingly, the tower was built to be the exact same height as the Siena Cathedral. If you are looking for unique views of the city and Cathedral, climbing the tower is a great way to discover the beauty of Siena. Entrance is not included in this tour.

Admission not included30 min

Make your way to the beating heart of Siena - the Siena Cathedral. At first sight, you will notice the breathtaking facade and its various colored marbles and a unique example of Romanesque-Gothic architecture. Inside, you will immediately be amazed by the incredible marble, mosaic floors, which depict biblical stories on 56 different scenes. As you look up, you will see masterpieces throughout the church from Renaissance masters including Donatello, Pisano, Pinturicchio, and Michelangelo. Walk through the breathtaking atmosphere inside, and don't forget to stop in the striking Piccolomini Library on your way out! Entrance is included in the price of this tour.

30 min

After a captivating morning of exploration in Siena, you can relax in the backseat of the air conditioned, luxury vehicle. Your driver will take you to San Gimignano along some of the most picturesque streets in Italy. Scenes that you have only seen in postcards will truly come to life! On this private tour, you have the perk of being able to ask your driver to stop as you prefer, so you can take incredible photos that will remain in your memory forever.

60 min

From a distance, you will begin to see San Gimignano, with its unmistakable medieval “skyscrapers.” Sometimes called a medieval Manhattan, there are still thirteen towers intact in this perfectly preserved hilltop town. Your driver will drop you off outside the ancient gate of the city, and where you can find a famous panoramic viewpoint of the Tuscan countryside. You will have an hour to explore the lovely town of San Gimignano as you please.

15 min

As you wander through the characteristic alleyways of San Gimignano, the streets will lead you to Piazza della Cisterna. This is the main square of the city, and where you can find the Cathedral, Duomo, and striking medieval architecture! You can grab a gelato or a coffee during your free time while enjoying the lovely views of this Renaissance city.

Admission not included15 min

During your free time in San Gimignano, discover the historic Cathedral and Duomo. Inside, you can find ancient and beautiful frescoes colorfully decorating the walls of the Cathedral. Many tourists skip entering this sacred church, and it is truly a hidden gem in the center of the town.

60 min

After exploring the timeless beauty of San Gimignano, it will be time to depart for a great symbol of Italy - Pisa! The drive will last about an hour, as you travel in complete comfort.

Admission not included30 min

With the Leaning Tower right in front of you, a visit inside will be irresistible! Enhance your experience in Pisa by making your way to the top of the Leaning Tower. From the peak, you can admire the stunning and diverse views of Pisa from above the rooftops of these ancient buildings. Enjoy the breeze on your skin, and then take some fun photos before heading back down! Admission fee is not included.

30 min

In the center of Piazza dei Miracoli, you will find the Cathedral of Pisa. Often overlooked by the Leaning Tower, this church is a hidden gem of pure beauty in Tuscany. The Cathedral is one of the first examples of “Pisan Romanesque” architecture, a form of design only found in Pisa and towns nearby. Discover the intricate carvings on the facade of the building, so precise it is almost unbelievable this was completed over almost a thousand years ago. Enter the Cathedral for truly heavenly views: Cimabue’s iconic fresches, Giovanni Pisano’s pulpit, and golden ceilings.

60 min

After grabbing some last minute souvenirs from Pisa, hop into the backseat of your comfortable, private vehicle, and you will be on your way. Enjoy the return drive in the comfort of a private, luxury vehicle. The drive will take about one hour, and you will be dropped off at your accommodation in Florence.

Highlights

Air conditioning and USB charger on board
Independent Sightseeing in Pisa, Siena and San Gimignano
Entrance to the Leaning Tower in Pisa - if option selected
Expert Professional Driver at your full disposal
Commentary on board
Bottled water
Door to door Hotel pickup and drop-off
Photo Stops along the Way to portray the most beautiful landscapes of Tuscany
Dedicated office support available before, during, and after the tour to customize the experience
Flexible itinerary
Direct access to the historic centre of UNESCO Listed Art Cities
Fully-fitted Mercedes vehicle with Free Wifi on board

What's included

Included
Air conditioning and USB charger on board
Independent Sightseeing in Pisa, Siena and San Gimignano
Entrance to the Leaning Tower in Pisa - if option selected
Expert Professional Driver at your full disposal
Commentary on board
Bottled water
Door to door Hotel pickup and drop-off
Photo Stops along the Way to portray the most beautiful landscapes of Tuscany
Dedicated office support available before, during, and after the tour to customize the experience
Flexible itinerary
Direct access to the historic centre of UNESCO Listed Art Cities
Fully-fitted Mercedes vehicle with Free Wifi on board
Not included
Lunch
Siena

Pickup Locations & Times

We also offer a pick up service to private homes and apartments

Traveller Ratings

4.8
149 reviews
5
137
4
6
3
1
2
3
1
2

Important Information

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Specialized infant seats are available
  • Not recommended for travelers with spinal injuries
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness

Reviews(149)

H
H184SVtinaf
July 6, 2026
A Fabulous Day in Tuscany

Today we spent an incredible 10 hours on a private tour with Ciao Florence Tours and Travels, and it absolutely did not disappoint! Our driver, Cristian, was fantastic. He was friendly, knowledgeable, and shared the history of every place we visited, which made the day even more special. Each winery was better than the last, and we enjoyed a delicious lunch at Teruzzi Winery. It was a perfect day in Tuscany and an experience we will always remember. Highly recommend!

J
jadaw318
May 30, 2026
My family and I had an amazing tour!!

Christian was an amazing driver with a rich knowledge of the history of Florence! We booked a tour from 8:30-5, and there was never a dull moment. He was friendly and had amazing recommendations for food, gelato, and photo opportunities. My family and I had a great time.

A
Ann H
May 19, 2026
Enjoyable time in Tuscany

We found Cris prompt, knowledgeable, enthusiastic, down to earth and very receptive to what we wanted in our tour. He really took good care of us. He slightly adjusted our tour to meet our needs and interests. Whenever possible, he took us the most scenic way to enjoy the Tuscan countryside. If our future guides during the rest of our time in Italy are half as good as Cris, we will continue to have a wonderful time! Bruce S & Ann H

Y
Yousuf_A
May 2, 2026
One of the best tours...

One of the best tours with a fantastic vineyard tour and lunch! Punctual with probably the best guide who made this trip efficient and memorable with two toddlers!

P
Patricia_V
April 7, 2026
A Must!!!! Fabulous

Christin was the most amazing guide!!! We had him for 10 hrs and it was outstanding!!! Christin also Went out of his way to find me the most amazing olive oil!!!

M
Manoj_P
March 29, 2026
An incredible private...

An incredible private tour that made exploring Tuscany effortless and memorable. Visiting the iconic Leaning Tower of Pisa was a highlight, and the charm of Siena and San Gimignano truly stood out. The guide was knowledgeable, friendly, and kept the day perfectly paced while sharing great insights along the way. Traveling by private car made everything comfortable and seamless. Highly recommend for anyone wanting to experience the beauty of Tuscany in a relaxed, personalized way!

G
George_V
September 7, 2025
Tuscan Super Man

If you are looking for the man who knows everyone in Florence, just call Placido. Placido was super and provided a wealth of information about Florence and Tuscany. What a great experience and a fun day. Top notch tour and Placido went above and beyond to make our day WONDERFUL. Thank you Placido from Georgia. We will call soon.

C
C8668AFjamesa
September 4, 2025
Incredible experience

Cristian was an incredible host with a vast knowledge of everything we experienced! Very easy to talk to and made our incredible trip even more special!

M
M6350WWta
September 4, 2025
Expertly Guided, Perfectly Planned, and So Memorable!

Our guide Christian was amazing! He really took the time initially to understand our preferences and personalized the trip for us — even updating timelines at each stop so we could spend more time on the experiences we would enjoy the most (and he was right!). He shared just the right details to help us navigate each site smoothly, while allowing us to relax and enjoy. His vast knowledge and engaging conversation throughout the day made it truly memorable. 10 hours flew by and we did and saw a lot. We couldn’t have asked for a better guide! Thank you!

C
Charles_I
August 26, 2025
A wonderful day touring the Tuscan region

What a wonderful day we had with tour guide Cristian, he expertly guided us around the crowds at all three destinations. This allowed to maximize what we experienced. Pisa was awesome, San Gimignano was charming and Siena’s square amazing. Cristian arranged for us to enjoy a scrumptious lunch and wine tasting, and shared interesting information about Italy and the places we visited. After a full day of touring Cristian expertly drove us back to our Villa. All in our party agreed that we thoroughly enjoyed the trip!

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