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Villages of Tuscany - Small Group
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13 hours ago
10 daysDuration
Group TourJoin a group of travelers
48 peopleMaximum group size
5 - 99 yearsAge range for participants
EnglishGuide language
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Highlights
Explore Rome, Orvieto, Pienza, Siena, Volterra, Grosseto and Pitigliano
See Roman Forum, Piazza del Campo and Duomo, Roman Theatre, and the Palazzo dei Priori
Visit a Contrada museum in Siena, the hilltop village of Orvieto and a local weekly market in Siena
Discover winemaking traditions in Montepulciano, the town of Orvieto by funicular, the timeless art of carving alabaster, the local traditions of the Sienese during the Palio and the importance of pecorino cheese in Pienza
Rome: Take in your first views of Rome on an orientation through the Italian capital, where ancient sites, grand squares and monumental landmarks reveal the scale of the city. Along the way, see the Roman Forum, centre of public life in ancient Rome, and the Trevi Fountain, one of Rome’s most famous Baroque landmarks.
Ride the funicular up to Orvieto’s old town, set on volcanic rock above the Umbrian plain. With your Travel Director, explore a town shaped by its strategic position, where narrow streets and historic buildings reveal a very different side of Umbria.
Montepulciano: Explore Montepulciano with your Travel Director before tasting Vino Nobile di Montepulciano, the DOCG red produced in the vineyards around the town. Made primarily from Sangiovese, known locally as Prugnolo Gentile, it is one of Tuscany’s best-known wines and a defining part of Montepulciano’s identity, served where the wine’s story begins.
Montalcino: Pause in Montalcino to take in views over the Val d’Orcia, the UNESCO-listed landscape seen in Gladiator. From this hilltop position, look out across the cypress-lined roads, fields and villages that have made this one of Tuscany’s most recognised landscapes.
Pienza: Explore Pienza with your Travel Director and get to know the town Pope Pius II reshaped as his ideal Renaissance city. Its orderly streets, stone buildings and compact historic centre give it a very different feel from Tuscany’s medieval hill towns. While you’re here, taste the pecorino cheese that has long been associated with Pienza and the surrounding countryside.
Siena: Visit the Mercato delle Merci, one of Tuscany’s biggest weekly markets, where locals come to shop for food, household goods and everyday essentials. Browse the stalls and look out for ricciarelli, the almond biscuits closely associated with the city.
Siena: With your Local Specialist, see Siena through the shell-shaped Piazza del Campo, home of the Palio, and the black-and-white marble Duomo, one of the city’s great artistic landmarks. Then step inside a district museum linked to the Palio, where you’ll find banners, costumes and historic memorabilia connected to one of Siena’s historic districts.
San Gimignano: Explore San Gimignano with your Travel Director, a UNESCO World Heritage Site known for the towers that still rise above the town. It was an important stop for pilgrims travelling the Via Francigena and grew wealthy through trade and passing traffic. Today, its preserved medieval centre and surviving towers make it one of Tuscany’s most recognisable hill towns.
Volterra: See how local artisans work alabaster, one of Volterra’s best-known materials and a craft closely tied to the town. As you watch this soft white stone being shaped, you’ll get closer to a tradition that has been part of Volterra since Etruscan times and remains one of its defining local industries.
Pitigliano: Get to know the Pitigliano’s Jewish history, which earned it the name Little Jerusalem. Built into tufa rock in southern Tuscany, the town became a place of refuge for Jews fleeing the Papal States in the 16th century. As you walk its streets, you’ll come across a story that sets Pitigliano apart from other Tuscan hilltop towns.
Step into Il Giardino dei Tarocchi and discover a very different side of Tuscany through the large-scale sculptures of artist Niki de Saint Phalle. As you explore the garden, you’ll see colour, mosaic and symbolism brought together in a setting that stands apart from the region’s medieval towns and hilltop villages.
Siena: Head into the Tuscan countryside for dinner at a local agriturismo, enjoy a wine tasting as you hear from the family about the history and culture of the region.
Ride the funicular up to Orvieto’s old town, set on volcanic rock above the Umbrian plain. With your Travel Director, explore a town shaped by its strategic position, where narrow streets and historic buildings reveal a very different side of Umbria.
Montepulciano: Explore Montepulciano with your Travel Director before tasting Vino Nobile di Montepulciano, the DOCG red produced in the vineyards around the town. Made primarily from Sangiovese, known locally as Prugnolo Gentile, it is one of Tuscany’s best-known wines and a defining part of Montepulciano’s identity, served where the wine’s story begins.
Montalcino: Pause in Montalcino to take in views over the Val d’Orcia, the UNESCO-listed landscape seen in Gladiator. From this hilltop position, look out across the cypress-lined roads, fields and villages that have made this one of Tuscany’s most recognised landscapes.
Pienza: Explore Pienza with your Travel Director and get to know the town Pope Pius II reshaped as his ideal Renaissance city. Its orderly streets, stone buildings and compact historic centre give it a very different feel from Tuscany’s medieval hill towns. While you’re here, taste the pecorino cheese that has long been associated with Pienza and the surrounding countryside.
Siena: Visit the Mercato delle Merci, one of Tuscany’s biggest weekly markets, where locals come to shop for food, household goods and everyday essentials. Browse the stalls and look out for ricciarelli, the almond biscuits closely associated with the city.
Siena: With your Local Specialist, see Siena through the shell-shaped Piazza del Campo, home of the Palio, and the black-and-white marble Duomo, one of the city’s great artistic landmarks. Then step inside a district museum linked to the Palio, where you’ll find banners, costumes and historic memorabilia connected to one of Siena’s historic districts.
San Gimignano: Explore San Gimignano with your Travel Director, a UNESCO World Heritage Site known for the towers that still rise above the town. It was an important stop for pilgrims travelling the Via Francigena and grew wealthy through trade and passing traffic. Today, its preserved medieval centre and surviving towers make it one of Tuscany’s most recognisable hill towns.
Volterra: See how local artisans work alabaster, one of Volterra’s best-known materials and a craft closely tied to the town. As you watch this soft white stone being shaped, you’ll get closer to a tradition that has been part of Volterra since Etruscan times and remains one of its defining local industries.
Pitigliano: Get to know the Pitigliano’s Jewish history, which earned it the name Little Jerusalem. Built into tufa rock in southern Tuscany, the town became a place of refuge for Jews fleeing the Papal States in the 16th century. As you walk its streets, you’ll come across a story that sets Pitigliano apart from other Tuscan hilltop towns.
Step into Il Giardino dei Tarocchi and discover a very different side of Tuscany through the large-scale sculptures of artist Niki de Saint Phalle. As you explore the garden, you’ll see colour, mosaic and symbolism brought together in a setting that stands apart from the region’s medieval towns and hilltop villages.
Siena: Head into the Tuscan countryside for dinner at a local agriturismo, enjoy a wine tasting as you hear from the family about the history and culture of the region.
What's Included
Accommodation
Cherrypicked hotels, all tried and trustedAll hotel tips, charges and local taxesOn occasion, hotels of similar standard and location may be utilised
Meals
Breakfast daily and up to half of your evening meals
Transport
Private airconditioned vehicle
Guide
An expert Travel Director and professional Driver
Others
All porterage and restaurant gratuitiesMustsee sightseeingAudio headsets for flexible sightseeingOptional Experiences and free time
Travel from Rome into Tuscany on a Small Group tour through hill towns, vineyards and cities shaped by local tradition. Taste Vino Nobile in Montepulciano, pause over the Val d’Orcia, shop Siena’s weekly market and explore Volterra’s Etruscan and medieval past. You’ll also visit San Gimignano, Orvieto and Pitigliano, and join a Be My Guest experience in the countryside before returning to Rome.
day 1Welcome to Rome
Arrive in Rome, a capital built on the legacy of the ancient empire and the power of the papacy, then meet your Travel Director before heading out on an orientation. You'll see the Roman Forum, where public life once unfolded in the heart of ancient Rome, and the Trevi Fountain, a Baroque landmark that shows a later chapter of the city at full scale. This evening, sit down to dinner with your fellow travellers as historic Rome sets the scene for the journey ahead.
