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Shore Excursions from Livorno to Siena and San Gimignano

driver with two guests and san gimignano

Private shore trip from Livorno to Siena and San Gimignano with private English speaking driver-guide.

A beautiful trip discovering the heart of Tuscany, travel immersed in the authentic Tuscan countryside shaped by vineyards and olive groves, by winding dirty roads climbing gentle hills bordered by lines of cypresses and end up to ancient farm-houses.

The shore excursion from the port of Livorno will take you discovering Siena and San Gimignano, two charming towns both UNESCO sites and framed in a perfect architecture of the landscape. Siena, home of the Palio (horse race) and home of the first bank ever founded in the world. Rich of art and traditions, deserves more time to be explored on your own or with a local guide.

San Gimignano is smaller but even charming. It lies on top f a hill that overlooks the Elsa river valley, rich of ancient tower-houses is also called “The Medieval Manhattan”. Here you can stroll after in its backstreets after a tasty lunch in a wine farm.

siena, main square with the comunal palace and the tower


Private tour with English-speaking driver.
Comfortable A/C minivan.
Travel through the authentic Tuscan countryside.
Visit the highlights of Siena at your own pace: Duomo, Piazza del Campo.
Visit San Gimignano on your own.
Snack lunch-Wine tasting in a local farm.
Eventual photo stop in Monteriggioni.


Meet the driver in Livorno and set off for your shore excursion to Siena, travel through the rolling hills of Tuscany as far as the home of Palio di Siena, the traditional horse race that has been running for centuries. Take your time to explore Piazza del Campo with the town hall palace, stroll along the main streets as far as the Duomo. During your visit, don’t miss tasting the local sweet specialties like Ricciarelli biscuits or the Panforte.

Afterward, depart to a winery immersed in the typical Tuscan countryside for savoring the local food specialties paired with the famous Chianti wines. 

In the afternoon, walk off the food and wine by strolling through San Gimignano. There is a lovely atmosphere in town, especially if you walk the backstreets of this village characterized by the presence of several tower-houses still standing since 1100 arriving also at 60-70 mt. height.

tuscany wine tasting, glasses of wine and bruscehttas

Price per person € 240,00 calculated on a base of 4 participants.
If your party is smaller or bigger, we will send you a customized quotation.



  • Private tour
  • Minimum #1 maximum #7 participants. If you have a bigger party we will arrange for you a bespoke program.
  • Full day English speaking driver.
  • Comfortable A/C minivan.
  • Lunch in local winery


  • Local tour guide
  • Museum tickets. We can make reservation/purchasing of skip-the-line tickets
  • Tips (optional).

Tour details

  • Meeting point: Livorno cruise terminal or nearby the ship.
  • Duration: 9 hours
  • Activity Level: Light: no special skills are required, and even people without a fitness base will enjoy these trips. The guided walks take place mostly on flat or slightly sloping surfaces, with a possibility of few steps to climb. If there are people with certain disabilities or needing to move with the wheelchair, please inform us, we will design a tour fitting your needs.
  • The tour runs with rain or shine, but in case of weather alert the tour can be modified or canceled.
  • Advised clothing: comfortable shoes and clothes, sunglasses, hat/cap, sunscreen.

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