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Three Days in Tuscany - Cortona, Pienza, Montalcino with Wine Tasting, Abbey of Sant'Antimo, Montepulciano

Private Tuscany tour includes:

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

Enjoy a Three-Day Mini-Tour from Rome to Tuscany featuring Cortona, Pienza, Montalcino and Montepulciano. This mini-tour package includes wine tastings and tours in Montalcino and Montepulciano, a guided tour of the ancient Etruscan hill town of Cortona, a visit to the Benedictine Abbey of Sant'Antimo and the historic sights of beautiful Pienza.

Day 1 - Travel to Cortona, Overnight in Cortona

You will have an early morning departure from Rome to make the most of our day in Cortona. After check-in at an elegant hotel, you will have a guided tour of Cortona, one of the oldest hill towns and best-preserved Etruscan cities in Tuscany. As you follow Cortona’s meandering medieval walls, you will be treated to magnificent views of vineyards, olive groves and Lake Trasimeno.  As you explore Cortona’s charming medieval streets, it will be clear why it was chosen as the setting for the movie “Under the Tuscan Sun.” The town is also known as the birthplace of the Renaissance painter Luca Signorelli. You will have free time to explore Cortona’s main attractions, including churches, museums, and the shopping area of Via Nazionale. You can also visit a very interesting Etruscan Academy displaying bronzes, vases and other objects from the Etruscan era.
Day 2 - Montalcino with Wine Tasting, Pienza, Abbey Sant'Antimo, Overnight in Cortona
Today your private tour of Tuscany will take you to Montalcino, Pienza and Sant'Antimo. First stop will be the wine-producing town of Montalcino, where you will visit the 14th century fortress, the cathedral and the old Etruscan hilltop streets dominating the valley for miles around. Montalcino is known as the birthplace of one of the finest wines of Italy, the Brunello di Montalcino. You will visit a wine producer and enjoy tasting their fine wines. You can pick up a few bottles of this fabulous red at a winery or in one of the shops you'll find on your stroll through the town of Montalcino.
Next your private tour of Tuscany will take you to the charming and picturesque town of Pienza. Pope Pius II conceived Pienza, his birthplace, as a Utopian “new town.” The construction of Pienza began in 1459; architect Bernardo Rossellino worked on its main sites under the guide of Leon Battista Alberti, the great theorist of Renaissance art, building and town planning.
You will have free time to explore Pienza. Time permitting, you may also enjoy the great shopping in Corso Rossellino, or visit the beautiful cathedral and the Pope Palace.
In the late afternoon, you 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.

Day 3 - Stop in Montepulciano, Transfer back Rome

Today you will have a lovely drive to reach the medieval and Renaissance town of Montepulciano.  It is one of the highest hill towns of Tuscany, built along a narrow tufa ridge, with a long main street and alleys that drop away to the walls. This car-free town, endowed with dozens of Renaissance palaces and churches, is a delight to explore on foot. It is also well known for its wine, which you may sample. You will return to Rome after your exploration of Montepulciano.


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