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Siena and San Gimignano
Livorno Shore Trips - Siena and San Gimignano
 



Private Siena and San Gimignano tour from the Livorno cruise port, visiting two UNESCO World Heritage historic centers in Tuscany. See Siena's Piazza del Campo and Duomo, then continue to San Gimignano, nicknamed Medieval Manhattan for its skyline of 13th century towers. Private English speaking driver guide, round trip from the Port of Livorno.

9 hours (private)
private excursion
driver guide
english speaking local
all group sizes
sedan to full size coach
››
port or hotel
pick up either location
  • Pick up from Port of Livorno
  • Your contact will hold a welcome sign with your name written
  • Private English Speaking Driver Guide
  • Round Trip Transportation in Private Vehicle
Read Full Tour Description





Tour Number:
ILIVO-05


Group Size (Prices in USD)*:
2 People - $626 Per Person
3 People - $416 Per Person
4 People - $320 Per Person
5 People - $256 Per Person
6 People - $214 Per Person
7 People - $196 Per Person
8 People - $172 Per Person



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TOUR DESCRIPTION
 

Siena & San Gimignano Shore Excursion from Livorno

This option explores both Siena and San Gimignano. It is the most popular tour for people who want to see typical Tuscan towns but also avoid the hordes of tourists in Florence and Pisa.

After meeting your driver guide at the pier in Livorno your exploration begins with a drive through the lovely Tuscan countryside to the historic town of Siena, located about 78 miles (126 km) from Livorno. Your driver guide will talk to you about sites you will see today, but you have the freedom to choose what interests you the most.

Upon arrival, you have time to visit Siena's pedestrian zone on foot. Siena's historic center is a UNESCO World Heritage Site. Explore the small medieval streets lined with splendid palaces. Many visitors like to visit the Cathedral to see the striking exterior which is lined with black and white marble. You might choose to visit the interior which is rich in frescoes, several statues made by Michelangelo, a pulpit which depicts scenes from Jesus' life. Also important to note is the inlaid marble floor which is decorated with religious symbols and stories.

You have time for lunch (meal not included), and Siena is loaded with cafes and restaurants serving Tuscan cuisine.

End your visit at the Piazza del Campo, one of the most beautiful squares in the world. The shell shaped square has been the center of Siena since the 1300s and it is still the hub of the city for both locals and tourists. On the square is the impressive Public Palace, where governors have lived for over 700 years. If you are up for a serious climb, you can ascend 400 steps to the top of the Mangia Tower for splendid views. This piazza is also the site of the world famous Palio race which is held every year. A rite of passage as a visitor is to lie on your back in the square and take in the city views and Tuscan sun.

Next you visit the Tuscan town of San Gimignano, a poster child for Tuscany and the epitome of a medieval Italian hilltop town. San Gimignano's historic center is also a UNESCO World Heritage Site. It gets the nickname "Medieval Manhattan" from its skyline of 14 medieval towers. By the 13th century the town had 72 towers and was home to many families whose fortunes grew from the fabric trade. The height of a family's tower was the sign of their wealth, and also served as a way to display their fabrics when unfurled from the top. In 1348 a plague devastated the town and ultimately lead to its decline and submission to Florence.

You visit the old town center on foot. There are several sites worth visiting but most people who are only here a short time just like to soak up the town's beauty and climb to the top of one of its towers for splendid views. There are also several places in town where you can sample local wines.

You may wish to visit the 13th century Palazzo del Popolo (The People's Palace) filled with coats of arms, frescoes by Sodoma and home of the Museo Civico featuring 14th century Florentine and Sienese art and decorative objects. Other favorites include the Duomo or Basilica of Santa Maria, consecrated in 1148, and frescoed with scenes depicting the Old and New Testament, and a noteworthy Last Judgment.

You may also choose to shop for local wares, including ceramics galleries and many quality leather shops.

At the end of the day, you return to the pier in Livorno.

If you cannot find what you are looking for, our Livorno tours and Livorno Shore Excursions can also be customized to fit your needs. If you have a larger group, we can offer you a private Livorno tour using a mid-size bus or full size coach. Please contact us with any questions or to receive a customized quote.

Please note
  • Mobility: Due to uneven surfaces, steps, and walking distances, this itinerary is not suitable for guests using wheelchairs. Please contact us for alternative sightseeing options, including private driving tours that may better accommodate your needs.

What's Included

Included

  • Pick up from Port of Livorno
  • Your contact will hold a welcome sign with your name written
  • Private English Speaking Driver Guide
  • Round Trip Transportation in Private Vehicle

Not Included

  • Meals and beverages not mentioned in the itinerary
  • Gratuities (optional, at your discretion)
  • Personal shopping

Tour Timing

All times are approximate and will vary based on your group's pace and interests.

  • 1
    2.5 Hours (traffic pending)
    Drive to Siena
  • 2
    2.5 Hours
    Explore Siena
  • 3
    45 Minutes
    Drive to San Gimignano
  • 4
    1.5 Hours
    Explore San Gimignano
  • 5
    1.5 Hours (traffic pending)
    Return to pier in Livorno

Resources

Port of Livorno, Porto di Livorno 2000 Cruise Terminal. Official cruise terminal operator, departure point for this excursion. Official Website

Frequently Asked Questions

What is the history of Siena?
Siena began as an Etruscan settlement called Sena before the Romans conquered it and renamed it Saena Julia in the 1st century CE. It grew into a self-governing commune by the 12th century and became one of medieval Italy's wealthiest city-states through banking and the wool trade. On September 4, 1260, Siena defeated rival Florence at the Battle of Montaperti, one of the bloodiest battles fought in medieval Italy.
Why is San Gimignano nicknamed Medieval Manhattan?
By the 13th century, wealthy families in San Gimignano had built as many as 72 stone towers, competing to display their wealth and status through height. Only 14 towers remain today, giving the small hilltop town a distinctive skyline that inspired the nickname.
Can you really visit both Siena and San Gimignano in one day?
Yes. The tour is structured around both stops, with about 2 to 2.5 hours to explore Siena, a short 45 minute drive to San Gimignano, and 1.5 hours to explore there before returning to the pier in Livorno.

Also Available:

›Flexible Florence and Pisa - another great option from this port: Tuscany and Florence shore excursion from Livorno cruise port - private guided visit to the Leaning Tower of Pisa and the Duomo (cathedral), a Romanesque masterpiece dating back to the 11th century with a licensed English-speaking driver guide.
›Extended Day - Florence and Pisa - prefer an organized full day covering both Florence and Pisa, this tour includes a licensed guide, entry into the Accademia or Uffizi Gallery, and stops at Giotto's bell tower and the Leaning Tower of Pisa
›Highlights of Rome - Rome shore excursion from Civitavecchia cruise port - private guided visit to the Coliseum, the Arch of Constantine, the Roman Forum, Trevi Fountain, the Spanish Steps, the Pantheon with a licensed English-speaking guide.
›Venice Highlights & Gondola ride - Venice shore excursion from Venice cruise port - private guided tour including a Grand Canal cruise, exterior visits to the Doge's Palace and St. Mark's Basilica, and a gondola ride through the canals with a licensed English-speaking guide.

Our Back-to-Ship Guarantee

Every excursion returning 1.5 hours before departure is covered. If we are late, we cover your costs to reach the next port. More info ›


Average Rating: Average Rating: 5 of 5 5 of 5 Total Reviews: 66 Write a review »

  3 of 3 people found this review helpful:
 
5 of 5 Review Location- Livorno Saturday, August 8, 2026
Reviewer: Walter H from Union Hall VA  
We had a wonderful vacation. Every one of the tour guides were great. My family was really impressed with their knowledge, service, and friendliness. I was pleasantly surprised with how much better an experience we had compared to the Princess Cruise Ship Tours. For example, our tour guide for the Amalfi Coast and Pompeii knew that Pompeii was closed until 1130 AM and changed our itinerary to travel along the coast in the morning and go to Pompeii at the end of the day. The other tours just took people to the gate and waited for two hours. Thanks again. My wife and kids felt that each guide was a   friend   by the end of the tour. The guides in Florence and Ephesus were probably the highlight for us. The Mercedes vans that were used in most cities were always nice and all of our drivers were really great. Ive already recommended you to a friend.

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  0 of 0 people found this review helpful:
 
5 of 5 Review Location- Livorno Sunday, August 2, 2026
Reviewer: Awilda L from Coral Gables FL  
We had a great time. Max did A great job. We really enjoyed it. Stefano was our driver a great help. Thank you.  We tipped him well.  Hope he remembers us!

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  0 of 0 people found this review helpful:
 
5 of 5 Review Location- Livorno Sunday, July 26, 2026
Reviewer: Anna A from Nicosia, Cyprus  
Indeed the private shore trip to Pisa and Florence was fantastic. Our driver, Max was very friendly and helpful.

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  0 of 0 people found this review helpful:
 
5 of 5 Review Location- Livorno Thursday, July 23, 2026
Reviewer: Ken Z from Calgary AB  
Today was our last excursion booked through your company. The trips in Florence and Nice were both great, with good hosts. But by far the best guide was Tom today in Kotor. He is excellent and I cannot say enough good about his knowledge and demeanor. 5 stars for him.Thanks for all

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  2 of 2 people found this review helpful:
 
5 of 5 Review Location- Livorno Sunday, June 14, 2026
Reviewer: David R from COVINGTON, LA  
We booked a few tours at last minute from our cruise ship as our Oceania shore excursions were pretty bad. We arranged our trip through Steven by email and Internet was spotty on the ship. He was quick to respond and was able to customize our trip for the day. We had 3 couples and Ynne was our guide. He was the best guide that we had had during our 12 day trip.

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