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Villages of Tuscany - Small Group
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.
Included With Your Trip
- An expert Travel Director and professional Driver Cherry-picked hotels, all tried and trusted All porterage and restaurant gratuities Private air-conditioned vehicle All hotel tips, charges and local taxes Breakfast daily and up to half of your evening meals Must-see sightseeing Audio headsets for flexible sightseeing Optional Experiences and free time On occasion, hotels of similar standard and location may be utilized
Additional Information
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Departure Dates
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Start: April 4, 2027 End: April 13, 2027 Price: $5,325 pp | Land Only Price My Trip |
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Start: April 18, 2027 End: April 27, 2027 Price: $5,325 pp | Land Only Price My Trip |
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Start: May 2, 2027 End: May 11, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: May 16, 2027 End: May 25, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: May 30, 2027 End: June 8, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: June 13, 2027 End: June 22, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: June 27, 2027 End: July 6, 2027 Price: $5,395 pp | Land Only Price My Trip |
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Start: July 11, 2027 End: July 20, 2027 Price: $5,395 pp | Land Only Price My Trip |
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Start: July 25, 2027 End: August 3, 2027 Price: $5,395 pp | Land Only Price My Trip |
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Start: August 8, 2027 End: August 17, 2027 Price: $5,395 pp | Land Only Price My Trip |
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Start: August 22, 2027 End: August 31, 2027 Price: $5,395 pp | Land Only Price My Trip |
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Start: September 5, 2027 End: September 14, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: September 19, 2027 End: September 28, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: October 3, 2027 End: October 12, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: October 17, 2027 End: October 26, 2027 Price: $5,425 pp | Land Only Price My Trip |
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Start: October 31, 2027 End: November 9, 2027 Price: $5,295 pp | Land Only Price My Trip |
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Product Code: TTUSAS-YVTUN27