Eyes of Rome

Shore Excursion: Siena and Chianti

Discover the Tuscan Countryside: Medieval villages and Tuscan Vineyards


  • Art
  • Food&Wine
  • History
  • Nature

What makes this tour Special

Have the chance to discover the intriguing history of the large medieval town that still practices their proud traditions.

You'll be driven into the heart of Tuscany, giving you the opportunity to admire the scenic views while driving between sites.

While you are surrounded by vineyards and Tuscan hills, you will be introduced to the best of Chianti wines at a family run winery.

What to Expect


Enjoy your tour with your own private tour expert at your party's disposal only


12 hours




Meet&Greet at your hotel/accomodation. Private Driver included throughout the tour


This tour is suitable for kids of all ages


You will be accompanied through this one day tour by your private driver guide.

What's Included
  • Meet & Greet your driver at Livorno Port
  • Round Trip from Livorno with Private English Speaking Driver

Not Included/ Optional Extras
  • Meals
  • Gratuities
  • Blue badge private guide in Siena (available upon request)
  • Entrance tickets to any desired sites

Sites you’ll visit

  • Port of Livorno
  • Siena
  • Chianti Countryside
  • The city of Livorno flourished under the Medici family, who turned it into a prosperous port. In the late 16th century Livorno was officially given the status of city and the architect Bernardo Buontalenti designed the city as an 'ideal town' with a population of 20,000 and a port that could hold 300 ships.
  • One of the must see highlights of Tuscany. Siena's historic centre is so beautiful and rich in medieval history, the entire centre is protected under UNESCO. The Medieval past is regularly showed with pride at the twice a year horse show, "il palio" - The city also carries a vast and deep rivalry with the capital of Tuscany, Florence, of which can be noticed throughout the various building designs.
  • Famous in the world as "The Rolling hills of Tuscany" is the Chianti countryside. Home to the best red wine producers in Italy and many opportunities to experience the wine making life with vineyard tours and quaint local bed and breakfasts.

Tour description

This is the perfect Shore Excursion if you want to experience the green Tuscan countryside at the fullest. 

You will have the chance to visit the medieval town of Siena and the greenish area of the Chianti’s Hills, renamed “Chiantishire”, famous for its characteristic vineyards.

Tasting the unique wine of this flourishing Region is something you can’t miss!

From meeting your Private driving guide at Livorno port, you'll be smoothly taken to the medieval hilltop city of Siena. The largest city in Tuscany to keep and regularly practice the tradition of their fruitful past. Learn from the local perspective of their strong and fearsome rivalry with neighbouring Florence that dates back to Italy's medieval times as well as the less gruesome tales of the now world famous, annual Palio horse racing event through the picturesque Piazza del Campo in central Siena.

Once your adventure of Siena has come to an end, you'll head right into the Chianti countryside to get a taste of what makes the hilly land so very famous in the world. In the heart of Chianti is a tranquil paradise of rolling landscapes and hidden family run wineries that you will get the chance to discover during this shore excursion.

After tasting the top Italian wines of Tuscany, you will take the relaxed journey back to the port of Livorno with your private driving guide.

Cancellation Policy

Please note that Eyes of Rome® applies the following cancellation policy for the selected product:

  • Eyes of Rome reserves the right to charge 50 % of your bookingfor no-shows or cancellations made within 168 hours of your tour date. For bookings confirmed through deposit-downpayment, Eyes of Rome reserves the right to charge the remaining tour balance on the day of the tour on the credit card provided during check out
  • For no shows on the day of the tour or cancellations/amendments requested less than 168 hours from the tour starting time, Eyes of Rome reserves the right to hold the amount paid during check out and charge any remaining balance for incomplete payments

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