Panorama of Siena, Tuscany, Italy

Explore Scenic Siena and San Gimignono

Tour and explore the beautiful, scenic cities of Siena and the cultural and agricultural heritage of San Gimignano in an air conditioned Mercedes sedan or limo minivan over the course of a 9-hour full day trip through the Tuscan countryside.

Your English speaking driver will pick you up at 8am in a private, deluxe car or minivan and drop you off at the dock on or before 5pm. You’ll be exploring the medieval architecture and historic edifices with your tour guide or independently.


  • Private, comfortable trip from Livorno port to Siena and San Gimignano and back to the port on time
  • See incredible medieval architecture in San Gimignano and its Fine Towers
  • Enjoy the picturesque scene as you drive through Tuscany
  • Visit the enduring crown-shaped fortress called Monteriggioni
  • Enjoy the “Vernaccia” wine
  • Admire the gothic cathedral in Siena
  • Participate in a bareback horse race in Siena



See One of the Most Spectacular Cathedrals in Italy in Siena

Your English speaking guide and chauffeur will come pick you at the Livorno port in an air conditioned Mercedes sedan, limo or minivan to help you explore these hilly towns. From there, it’s a straight two hour drive through the beautiful countryside of Tuscany to Siena.

While you’re here, your guide will show you the best sights and attractions in the city. Siena is so rich in history and culture that you can actually feel some of it as you walk the quaint, beautiful back streets.

Major tourist attractions you want to see in Siena are the gothic Cathedral of Siena which is an architectural masterpiece. And for book lovers, the huge library called the Piazza del Campo provides enough activities. Your guide will also take you to the Torre del Mangia.

Your guide will also take you through the Jewish Ghetto, while informing you of the upcoming bareback horse race called the Palio di Siena which takes place twice a year on the 2nd of July and the 16th of August.

If this interests you, try booking early to visit on these two days. The horse race which holds in the Piazza del Duomo is considered the most important event in the city every year because of its historical significance, and brings out the spirit of patriotism and fierce competitiveness in the locals.

While in the Piazza del Duomo, you can explore the architectural and artistic masterpieces of the cathedral and its surrounding buildings on foot. Your guide will also show you another magnificent architecture that’s a castle within a castle (Castellare degli Ugurgieri). The city is small enough for walking and seeing everything that’s interesting, so this will be a walking tour.

Your guide will also suggest excellent local cuisines and wines that you eat and drink for lunch whilst taking a break and preparing for the second part of the tour to San Gimignano.

Once done, your driver will take you to San Gimignano. On your way, you’ll stop over at the charming little village of Monteriggioni with its impressive walls. This is one of Italy’s most popular walled cities. Foodies looking to have a taste of true Tuscan meals in a proper trattoria can do so here.

Experience the Hilltop City

Once you’re done in Monteriggioni, you can then proceed on your second leg of the tour, to San Gimignano, a hilltop city with its enduring 14 towers –there were 72 initially- that have been there since the 11th century.

This Medieval Manhattan of Tuscany city is located on a hilltop that overlooks the Elsa Valley, providing an amazing aerial view of the green, lush valley. The 14 towers and adjoining medieval architecture make up what is known as its historic center “San Gimignano delle belle Torri”, which is listed as part of UNESCO’s world heritage sites.

Activities here include walking the tiny, winding medieval walkways between the towers, whilst listening to the history of the place and commentary by your guide, going to the Piazza della Cisterna with its surrounding beautiful towers and palaces to get some locally made souvenirs as well grab some food if you’re hungry. Gelato lovers will get the absolute best gelato there is in Tuscany at the gelateria also located at the square.

Once done at 3.00pm, you can hop in the vehicle and enjoy the comfortable 1hr 40mins ride back to Livorno port knowing you have ticked off one of the items on your bucket list.


  • Siena
  • Monteriggioni
  • San Gimignano


  • Transportation from/to the Livorno port
  • Mineral Water
  • Visit to Siena
  • Visit to Monteriggioni
  • Visit to Gimignano


  • Fee for local operator guided tour Florence
  • Cost of lunch
  • Gratuities –solely at the client’s discretion

Meeting Point: 

Arranged meeting at Livorno port.


From 1 to 8 passengers travel in a Mercedes class sedan or minivan limo.

Pricing is based on number in your private tour or tour package and may be modified by seasonal prices. Email us the tour you are interested in and number in your tour and we will provide you our most affordable quote.

Once arrangements are settled and with your approval we will send you an invoice for 10% down via paypal then remainder to be collected at the end of the trip. The English-speaking driver will pick you up at the port of Livorno, at the terminal where cruise-ships dock. You will meet your guide directly in Florence.

The English-speaking driver will pick you up at the port of Livorno, at the terminal where cruise-ships dock. At the end of the excursion you will be taken back to the port of Livorno for other appointments you might have. is a transport service and transport host and is not a travel agency. Our job is to escort you on your visit and provide you with affordable professional transportation to your choice of attractions and destinations and return you to your appointed destination. Our knowledgeable and professional drivers will avail all their knowledge of the locale and suggest and avail you to top local professional guides, wineries, and local services