Prestige Rent

Private Tour to Siena & San Gimignano from Livorno Port

Wander the Tuscan countryside, discover Siena and San Gimignano from Livorno Port! Enjoy the perfect experience exploring 2 medieval gems

from €650β‰ˆ $751 Β· Β£556Other currencies at today’s rate β€” you are charged in euro

Location:
Livorno
Duration:
9 hours
Language:
English
Tour type:
Shore excursion
Group:
Your party only
Free cancellation:
Up to 24 hrs
Ticket:
E-ticket on your phone
  • Back on board before all aboard, guaranteed
Private Tour to Siena & San Gimignano from Livorno Port
Private Tour to Siena & San Gimignano from Livorno Port
Private Tour to Siena & San Gimignano from Livorno Port
Private Tour to Siena & San Gimignano from Livorno Port
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Why you will remember it

  • Free cancellation up to 24 hrs – no charge if ship misses port – full refund if cruise is canceled
  • Private is just for you! Pick up/drop off directly at your ship
  • Enjoy a private tour to Siena and San Gimignano from Livorno Port: explore two beautiful medieval cities
  • See the magnificent Cathedral , the shell-shaped Piazza del Campo and much more
  • Fall in love with Tuscany, driving through marvelous postcard views
  • Stroll around picturesque San Gimignano famous for its medieval towers and local wine
  • Relaxing worry-free ride back to Livorno Port, with guaranteed on-time return to your ship
Free cancellation up to 24h β€” 100% refundInstant confirmationBest price guaranteed β€” no booking fee

The itinerary

Wander Tuscany, discover Siena and San Gimignano from Livorno

The perfect experience to visit two of the most charming medieval cities in Tuscany and the world-famous Tuscan countryside. See the highlights of Siena, take a picture of the hilltop fortress in Monteriggioni, admire the beautiful Tuscan countryside and walk narrow quaint streets in San Gimignano from Livorno!

SIENA

Your private day to Siena and San Gimignano from Livorno Port starts with a scenic one-hour drive through the Tuscan countryside. The first stop is Siena, the birthplace of the beloved Italian Saint Catherine.

Wander narrow streets and medieval towers

This beautiful city is made of brown Siena-colored bricks, that’s how they named the color! A jumble of narrow streets and delightful squares with medieval towers that make a spectacular skyline, the magnificent Cathedral and the tall and trim Torre del Mangia. Enjoy the enticing atmosphere almost like stepping back in time.

Discover famous Piazza del Campo

Siena was built on three hills and is home to one of the most authentic and important Gothic cathedrals. Despite the city’s architectural masterpieces, it is the unusual shell-shaped Piazza del Campo that receives the most consideration, famous location for films and photographs.

Palio race

In this brick-covered square twice a year takes place the famous Palio horserace. It involves the entire population and it is considered one of the most important events in the life of the Senese people. Almost anything will be done to win this extremely competitive race and bring home the palio, a silk banner proudly displayed in the ‘contrada’ or neighborhood it represents.

MONTERIGGIONI

Stop in Monteriggioni, a 13th-century hilltop fortress. A tiny village that has maintained its original defensive walls and medieval atmosphere, surrounded by spectacular views over the countryside.

TUSCAN COUNTRYSIDE

While traveling to San Gimignano, admire the typical Tuscan landscape with postcard views over vineyards, olive groves, rolling hills and old stone buildings and wineries.

SAN GIMIGNANO

Explore medieval San Gimignano, a small town in Tuscany famous for its splendid skyline made up of 13 towers! This hilltop 11th-century town rises along the ancient road ‘Via Francigena’ on which traders and pilgrims going to Rome traveled. San Gimignano prospered considerably during this period thanks to this route and all the inns built along its way to host travelers.

Ancient towers and museums

Besides its 13 remaining towers, see the ‘Duomo’ or Collegiate Church and its magnificent frescoes, ‘Palazzo del Popolo‘ and ‘Palazzo Nuovo del PodestΓ ’ now the town hall. Enter the church dedicated to Saint Augustine, the Museum of Holy Relics, and the infamous Museum of Torture with its macabre displays of early torture instruments.

Today, its important cultural and natural heritage has been recognized by UNESCO.

Local crafts

Wander up and down the main street in San Gimignano, go in and out of the numerous specialty shops! The ceramics are beautiful here and there are also places for buying leather goods and linens.

Taste vernaccia wine

Are you a food and wine lover? Many shops and wine bars have delicious local products including the Vernaccia wine typical from here, one of the most ancient grape varieties in Italy even mentioned by Dante Alighieri in his Divine Comedy!

Your perfect tour to Siena and San Gimignano from Livorno Port ends with a relaxing drive back to your ship.

This tour β€” everything you need to know

Included:

  • Private service: your party will be the only one in the vehicle
  • Free Cancellation up to 24 hours prior to departure
  • Special Prestige Rent’s worry-free policy for cruisers: guaranteed on-time return to your ship – no charge if ship misses port – full refund if cruise is canceled
  • Pick up and drop off directly at your ship in Livorno Port
  • Knowledgeable English-speaking driver to lead you through the experience
  • Transport with fully equipped Mercedes vehicle, free Wi-Fi and fresh bottled water
  • Free time to visit Siena at your own pace
  • Free time to visit San Gimignano at your own pace
  • All taxes, tolls and gasoline
  • No hidden costs

Not Included:

  • Entrance fees (if applicable)
  • Meals

Optional:

  • Gratuities
  • Private local guide for 2 hours in Siena (Euro 250.00 per party)
  • Winery visit with wine tasting – Approx. Euro 40.00 per person
  • Winery visit with wine tasting and light lunch – Approx. Euro 70.00 per person
  • Extra hours to extend your day, Euro 90.00 per hour, per party, (if feasible according to your ship schedule)
Viator Experience Award Winner 2025 and 2023 β€” rated 4.9 out of 5 on Viator and TripadvisorTripadvisor Travelers' Choice Awards 2025
1.1M+guests since 2000
4.9average guest rating

What our guests actually say

Every review below is public on the platform it came from.

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Mario is a Wonderful Driver
Mario was a wonderful driver! He is so kind, knowledgeable, and accommodating. We asked if we could go to Volterra and Siena instead of the original itinerary, and he did this for us. We were even able to stop at Monteriggioni. We highly recommend him!
Mary B. Β· July 2026
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Amazing day in Tuscany
Donatello was AWESOME and we recommend him highly. By the end of the day he felt like an old friend. He was willing to customize our route to our preferences including taking us to the Elsa cascades. Our day was the perfect mix of info and conversation with Donatello and alone time to wander. We had a fantastic time and recommend this excursion, Donatello, and Prestige very highly. Would not hesitate to book again. Thank you much Donatello!
Erica J. Β· May 2024
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Great day in Siena and San Gimignano
Our driver/tour guide, Donatello, was wonderful! He was waiting for us as we got off our ship with a clean and new Mercedes van. He gave us lots of great information about our two planned stops, plus two other fabulous and unplanned stops that he suggested. It was a great day and our group of 6 were so happy with the wonderful day. I highly recommend using PrestigeRent!
Julie L. Β· October 2023
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Wonderful day with a great driver!
Instead of doing the crowded and overrated cruise excursion, we opted for a private car and driver through Prestige Rent. The car was impeccably clean and the driver, Donatello was wonderful. He was knowledgeable, personable and entertaining. Once we told him what we wanted to do, he made suggestions that improved our experience. We spent the day visiting walled hill-top towns, wine tasting, and general sightseeing. Furthermore, every email I sent to…
Cindy M. Β· September 2023

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The Prestige Rent team in Italy β€” real people ready to help you

Have questions? Let’s chat!

Meet our native English-speaking experts, Violeta and Carrie. A different pick-up time, a second vehicle for a larger family, a licensed guide, a winery to add, a wheelchair to fit in the boot, a drop-off at the airport on your last day β€” tell them what your day needs to look like and they will build it.

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Private Tour to Siena & San Gimignano from Livorno Port
from €650 per partyβ‰ˆ $751 Β· Β£556
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