Pienza - San Gimignano

Cultural Tuscan Hill Towns

Pienza - San Gimignano
Dates From
6 Nights
7 Days
Price From
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Three night stays in the small Tuscan hill towns of Renaissance Pienza, the ideal city, and medieval San Gimignano, the city of beautiful towers. Brunello and Chianti wine tastings at Montalcino and Castellina in Chianti. A Pecorino cheese factory visit at Montepulciano. Step back 2,500 years at ancient Etruscan sites in Sovana and Pitigliano and the Etruscan Museum at Cortona. Italy’s most beautiful square, the Piazza del Campo, at Siena. The 9th century Abbey ofSant’ Antimo, pici pasta and the fabulous vistas of the Orcia Valley are just a few more of the highlights. Michelangelo’s David at the Accademia Museum and a pre tour exploration of Florence is included!


  • All activities and admissions
  • Pickup Florence & Pisa airports at scheduled times
  • 6 nights accommodation in charming hotels
  • Tourist accommodation tax
  • All breakfasts, 3 dinners, beverages included
  • Full-time professional tour manager
  • Porterage
  • All ground transportation Days 2 - 6
  • Morning transfers to Florence & Pisa airports, station or hotel


Day 1

The name Tuscany means “land of the Etruscans“. These were the ancient peoples who controlled a large part of the Italian peninsula prior to the rise of the Romans. They were great builders and engineers. Many of their temples and roads and burial chambers can still be seen today. They drained swamps, had indoor plumbing and painted frescos. Etruscan women were allowed to own property and drive chariots.

The obvious reason the ancient Etruscans and their successors constructed their towns on hilltops was for defense. Another reason was to avoid lowland swamps and malaria-carrying mosquitoes. The location of  the Tuscan hill towns has not changed so be prepared for winding roads and wonderful vistas.

Our early afternoon transfer is from Florence airport where you’ll be met by your tour manager. Heading south into the heart of Tuscany our first stop is the 13th century walled fortress of Monteriggioni; the ancient hamlet within still retains its original appearance and counts just 42 inhabitants.

Then we transfer to one of the most charming towns in Italy, Pienza, the Renaissance “ideal city”. Constructed in the latter part of the 15th century at the behest of native son Pope Pius II Pienza overlooks the rolling cypress-lined hills of the stunning Orcia Valley. Our lodging is Hotel Corsignano (3 nights) located just outside the town walls. Introduction to the delicious local cuisine at our welcome dinner.

Day 2

Cortona, one of the original 12 Etruscan city-states, is reputably the oldest continuously inhabited town in Italy. Situated on a commanding hill overlooking Lake Trasimeno, it has cyclopean walls – huge boulders roughly fitted together without mortar – that date back 3,000 years.

Cortona was conquered in the 16th century by Florence. We’ll begin our morning with a look at the Medici fortress after which we’ll learn about Cortona’s earliest residents at the Museum of the Etruscan Academy.  Winding lanes, medieval squares and great small restaurants await your midday break.

Montepulciano, which has its roots in Roman times, is home to grand piazzas, noble palazzos and ancient alleys. After a guided walking tour we’ll complete our visit with a tasting of pecorino at a cheese factory served with local wines.

Day 3

This morning we go to the very south of Tuscany passing through mysterious landscapes to visit the tiny town of Sovana and the nearby Archaeological Park where we’ll have a fascinating guided tour of the 2,700 year old Etruscan necropolis and the profound experience of walking along ancient Etruscan roads.

Pitigliano is one of the most unusual towns you can imagine, sitting atop a sheer cliff lined with holes that were once Etruscan tombs and now used as cantinas, stables and storehouses. It has a lovely medieval center with 16th century fortress, massive aqueduct and old Jewish ghetto.

Included dinner in Pienza.

Day 4

An early morning visit to the vineyards and cantina of Il Casato to have a taste of their Brunello wines. Then we’ll take in the hill-town and castle of Montalcino, with some of the most scenic settings on our tour.

Afternoon visit to the beautiful 9th century abbey St. Antimo where we’ll hear the monks’ Gregorian chants.

San Gimignano, originally an Etruscan settlement, became an important medieval town due to its location along the Francigena Way – the famous pilgrim route from northern Europe to Rome. It’s known as the city of the beautiful towers – once there were 72, now 14. In 1353 it was overpowered by the might of Florence and was forbidden further construction. In addition, the Francigena Way was relocated – diminishing the city’s importance. The result is that, today, San Gimignano retains its same charming 14th century appearance. We’ll be staying at the 13th century Hotel La Cisterna , set in the main square of town.

Day 5

Early morning free in San Gimignano followed by a drive into Chianti wine country. Our first stop is Castellina in Chianti, an attractive hill-town that was once the fortified border between Florence and Siena. It still retains its 15th century defensive look with imposing walls and fortress but these days is more inviting with shops vending wine, olive oil and other local products.
This afternoon we’ll have a guided tour of a local vineyard and taste their Chianti wines.

Day 6

Our last excursion is to the enchanting Gothic city of Siena, home to one of Italy’s most beautiful squares, the Piazza del Campo and a marvelous cathedral. Originally founded as a Roman military colony, Siena flourished during medieval times as an important banking center and was a powerful rival to Florence. In the mid 14th century the Black Death put a halt to cathedral construction as Siena lost 70% of its population. The combined might of Spain and the Medici family put an end to the Republic of Siena in 1559.

Our local guide will walk us through the contrade (wards) of Siena with an entertaining explanation of their role in contemporary social life and the competition of the famous horse race, the Palio. After which we’ll leave you on your own for shopping, lunch and, perhaps, to climb the 503-step Torre del Mangia.

Our San Gimignano farewell dinner restaurant is located in the historic center with stunning views over the valley.

Day 7

Morning transfers to Florence airport, train station & hotels; Pisa airport.


Starts Ends Price Status Book
18/10/201924/10/2019$3,500 p/p twin shareAvailable
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29/05/202004/06/2020$3,650 p/p twin shareAvailable
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23/10/202029/10/2020$3,650 p/p twin shareAvailable
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Single supplement (is available if required)
Optional excursions/sightseeing
Meals and beverages other than those specified
Everything which is not clearly specified under inclusions