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Three Days in Tuscany - Siena, Pienza and Chianti with Wine Tasting

Private Tuscany tour includes:

  • Three Days of Touring
  • Private transportation for transfers and tours as indicated in the itinerary
  • Services of your driver guide
  • Wine tasting in Chianti
  • Accommodations at a four-star hotel for two nights
  • Taxes, parking, tolls

Enjoy a three-day, mini-trip from Rome to Tuscany featuring tours of Siena, Pienza and Chianti with wine tasting. Explore the historic sights and streets of Pienza and Siena, and savor a day in scenic Chianti sampling wines during your tours of Greve and Castellina-in-Chianti.

Day 1 - Travel to Siena, Overnight in Siena

You will have an early morning departure from Rome to Siena, the first stop on your mini-trip to Tuscany. Built on three hills in the middle of the Via Francigena (pilgrimage road), Siena is one of Tuscany's crown jewels. It has an outstanding Gothic Duomo and another important church, San Domenico, which claims the skull of St. Caterine. It also has one of the most beautiful squares in Italy, il Campo, where the famous Palio horse race is held twice a year.

Your private guided tour will give you an overview of Siena's most important neighborhoods, squares and churches, before giving you some time to explore them on your own.
Day 2 - Chianti Tour: Greve, Castellina-in-Chianti, Wine Tasting, Overnight in Siena

Today you will enjoy a private tour of Chianti, Tuscany's most picturesque area, a territory of vineyards and hill-towns that stretches from Florence to Siena. The Chianti region, known all over the world for its great wines, offers travelers scenic roads dotted with cypress trees, grapevines and olive groves.

Your Chianti private tour will take you to one of the nicest villages in the Chianti area, Greve. There are several wine shops, including a small wine museum where you can taste and purchase wine and olive oil. There are also numerous shops surrounding Greve’s main square, Piazza Matteotti. You’ll have free time for lunch in Greve before going to another winery for more wine tasting. 

Your guided Chianti tour will also take you to Castellina-in-Chianti, another lovely town of the Chianti area. You will return to your hotel at Siena at the end of the day.

Day 3 - Transfer back to Rome, Stop in Pienza and Abbey Sant'Antimo.

Today, before returning back to Rome, you will have a stop in the charming Renaissance town of Pienza. This town sits at the heart of the Orcia Valley, a spectacular area that stretches from Montepucliano to San Quirico. You will be treated to a beautiful landscape dotted with cypress trees and other vegetation. 

You will have free time to wander through the lovely streets of Pienza.  Note the street names:  Via dell’Amore (Street of Love), Via del Bacio (Street of the Kiss), and Via della Fortuna (Street of Luck). The beautiful Via del Casello has a spectacular panoramic view of the Orcia Valley.  You may also enjoy the great shopping in Corso Rossellino, or visit the beautiful cathedral and the Pope Palace.  Pienza is known all over Italy for its fragrant, flavorful Pecorino cheese, which you can sample here. In the late afternoon, we will continue traveling Tuscany's backroads to reach the Romanesque Abbey of Sant'Antimo, an unforgettable 9th-century Benedictine monastery. It is a simple yet magnificent stone church, set amongst the field of olive trees. An important monastic community once flourished here; today, the monks here follow the rule of St. Benedict, praying seven times a day with Gregorian chants.

We will transfer you back to your hotel in Rome at the end of the day.

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