Vacation Overview
Tour Details
Villages Of Tuscany - Small GroupTravel 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.
Dining Summary- 5 Dinner (D)
- 9 Breakfast (B)
Must-see Highlights- Explore Rome, Orvieto, Pienza, Siena, Volterra, Grosseto and Pitigliano
- See Roman Forum, Piazza del Campo and Duomo, Roman Theater and the Palazzo dei Priori
- Visit the hilltop village of Orvieto, a Contrada museum in Siena, and a local weekly market in Siena
- Discover Rome, the town of Orvieto by funicular, winemaking traditions in Montepulciano, the importance of pecorino cheese in Pienza, the local traditions of the Sienese during the Palio and the timeless art of carving alabaster
Iconic Experience- 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, center 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 recognized 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 center 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 traveling the Via Francigena and grew wealthy through trade and passing traffic. Today, its preserved medieval center and surviving towers make it one of Tuscany’s most recognizable 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 color, mosaic and symbolism brought together in a setting that stands apart from the region’s medieval towns and hilltop villages.
Be My Guest- 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.
Daily Itinerary
Trafalgar Tours: Villages of Tuscany - Small Group
Day 1 - Welcome 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 travelers as historic Rome sets the scene for the journey ahead.
Meals: Dinner
Day 2 - Head into the Tuscan Countryside
Travel to Orvieto and ride the funicular up to its hilltop old town, where your Travel Director introduces you to this Umbrian city of volcanic stone, cathedral facades and streets built high above the valley below. Take time to explore at your own pace and find somewhere local for lunch. Continue through Tuscany’s wine region, a landscape shaped by vineyards and long-standing wine traditions, before arriving in Montepulciano for an orientation of the village with your Travel Director. Later, you’ll enjoy a tasting of local wines and discover the character of one of Italy’s best-known wine regions.
Meals: Breakfast
Day 3 - Views and Tastes of Tuscany
Spend the day in two of southern Tuscany’s best-known hilltop towns. In Montalcino, join your Travel Director for an orientation, then take time to explore and pause for a cappuccino with views over the Val d’Orcia. Continue to Pienza, the Renaissance town created under Pope Pius II, where your Travel Director introduces the layout and history of this UNESCO-listed center. Then taste the pecorino cheese the town is known for before free time for lunch. Later, return to Montepulciano, where the evening is yours to relax or head out with your small group for a plate of pici all’aglione in town.
Meals: Breakfast, Dinner
Day 4 - A Day in Siena
Drive through the Tuscan countryside to Siena, a medieval city best known for the shell-shaped Piazza del Campo and its Gothic Duomo. Spend time at the Mercato delle Merci, one of Tuscany’s biggest weekly markets, where locals come to shop for everything from food to everyday goods. Browse the stalls, step into Siena’s small stores and perhaps try panforte, the dense fruit and nut cake closely tied to the city. Later, join your Local Specialist to explore Siena’s historic districts, see the Piazza del Campo and Duomo, and visit a contrada museum.
Meals: Breakfast
Day 5 - Walls of Chianti and on to San Gimignano
Start in Certaldo, where your Travel Director introduces a hill town with strong medieval roots in the heart of Val d’Elsa. You’ll have time to walk the walls, look out across Chianti and perhaps settle into the square for a cappuccino before exploring the shops and museums. Continue to San Gimignano, the UNESCO-listed town that rose to prominence on the Via Francigena pilgrimage route and is still known for its skyline of medieval towers. Later, head into the Tuscan countryside for your Be My Guest experience at a local agriturismo, where wine, history and local culture come together.
Meals: Breakfast, Dinner
Day 6 - Crafts of Volterra
Head to Volterra with your Travel Director to explore a hill town known for its Etruscan roots and medieval streets. In the historic center, see the Roman Theater, the Cathedral and the Palazzo dei Priori, the oldest town hall in Tuscany. You’ll also get to witness the ancient local tradition of alabaster sculpting, one of Volterra’s best-known crafts, and for which the town is still renowned today.
Meals: Breakfast
Day 7 - South through Tuscany
Enjoy a morning a leisure in Volterra with time to explore more of the town at your own pace. Then head south to the Abbey of San Galgano, where the roofless church and monastic ruins make a striking stop in the Tuscan countryside. Continue to Grosseto, a walled city in southern Tuscany, for an orientation with your Travel Director. As you get your bearings, see the layout and landmarks of a historic center shaped by Medici rule and still enclosed by its star-shaped walls.
Meals: Breakfast, Dinner
Day 8 - Thermal Baths and Hilltowns of Tuscany
Stop at Cascate del Mulino, part of the thermal baths of Saturnia, where mineral-rich waters flow through the white limestone pools. Then continue to Pitigliano with your Travel Director and explore one of southern Tuscany’s most distinctive hill towns. Built into tufa rock and known as Little Jerusalem for its long Jewish history, Pitigliano stands out for both its setting and its story. As you walk through the town, take in its lanes, arches and views before time to look around further at your own pace.
Meals: Breakfast
Day 9 - Etruscan Legacies and Return to Rome
This morning make your way to the enchanting hilltop village of Capalbio, also known as "Little Athens". Visit Il Giardino dei Tarocchi, where large-scale sculptures by Niki de Saint Phalle bring color and character to the Tuscan landscape. This evening, you’ll gather for dinner with your small group and raise a glass to your journey through Tuscany.
Meals: Breakfast, Dinner
Day 10 - Arrivederci Roma
Your journey through Tuscany comes to an end today as you say goodbye to your Travel Director and fellow travelers. Take with you the hilltop towns, local flavors and moments shared along the way.
Meals: Breakfast