Journey from the timeless streets of Rome into the heart of Tuscany, where rolling vineyards, medieval hill towns, and breathtaking landscapes create one of Italy’s most unforgettable regions.
Discover the Renaissance beauty of Montepulciano while sampling its world-famous Vino Nobile, take in the spectacular views across the UNESCO-listed Val d’Orcia, explore the lively piazzas and historic streets of Siena, and uncover the fascinating Etruscan heritage of Volterra.
This immersive Tuscany experience blends authentic wine, rich history, and unforgettable scenery into a journey you’ll treasure for a lifetime.
Join us on this small group tour of up to 18 travelers journeying through Italy’s most iconic Tuscan towns for an experience of a lifetime!
Submit form for air itinerary and price of the tour with airfare from your city.
Highlights
Tuscany Sightseeing Highlights
- Rome Orientation Walk
- Visit Orvieto Hilltop Village
- Visit Montepulciano and Taste Vino Nobile Wine
- Views of Val d’Orcia
- Orientation and Pecorino Tasting in Pienza
- Sightseeing in Siena with Visit to Contrada Museum
- Visit San Gimignano
- Enjoy Dinner at an Agriturismo
- Volterra visit Alabaster Workshop
- Visit Pitigliano
Tuscany Tour Includes
- Small group up to 18 travelers.
- Airline taxes & fuel surcharges
- 9 nights First Class accommodations
- Airport transfers with air inclusive Italy tour package
- All transfers between cities in Italy
- Daily Breakfast & 5 Dinners
- Sightseeing per itinerary in modern air-conditioned motor coach
Accommodations
Precise House Mantegna Roma, Rome – 1 Night ★★★★
Montepulciano – 2 Nights ★★★★
Siena – 2 Nights ★★★★
Volterra – 1 Night ★★★★
Grosseto – 2 Nights ★★★★
Rome – 1 Night ★★★★
Optional Tours
Optional tours are not included in the base price. They are scheduled during free time.
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Tuscany Tour Daily Itinerary
DAY 1, Depart the USA For Overnight flight to Italy
Depart the USA for Italy. Your flight includes meals, drinks, and in-flight entertainment for your journey
DAY 2, Arrive in Rome
Arrive in Rome, the Eternal City, and transfer to your hotel.
Depending on your arrival time, you have the freedom to start exploring this romantic and historic city at your leisure. Experience the enchantment of Rome as evening sets in, when its streets come alive with a captivating charm.
Wander through picturesque streets and charming piazzas, immersing yourself in the city’s world-renowned gastronomy.
Enjoy an overnight stay in Rome, soaking in the atmosphere of this timeless destination
Overnight: Rome
Meals: Dinner
DAY 3, Rome to Orvieto and Montepulciano
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.
Afterward, 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.
Overnight: Montepulciano
Meals: Breakfast
DAY 4, 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.
Overnight: Montepulciano
Meals: Breakfast & Dinner
DAY 5, 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.
Overnight: Siena
Meals: Breakfast
DAY 6, 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 dinner at a local agriturismo, where wine, history and local culture come together.
Overnight: Siena & Dinner
Meals: Breakfast
DAY 7, 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.
Overnight: Volterra
Meals: Breakfast
DAY 8, 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.
Overnight: Grosseto
Meals: Breakfast & Dinner
DAY 9, 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.
Day 10, 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.
Overnight: Rome
Meals: Breakfast & Dinner
Day 11, Tour Ends in Rome
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.
