Hill Towns of Italy



Join us for an enriching discovery of Tuscany and Umbria, regions cherished the world over for its breathtaking natural beauty, superb cuisine, delectable wines and rich cultural heritage. Tuscany’s historic hilltop towns are living postcards, where ancient ramparts encircle colorful piazzas, elegant Etruscan fountains, stately palazzos and bustling cafés. Settle in Cortona and join excursions to Orvieto, Montepulciano, Siena and Assisi. Uncover Cortona’s Etruscan legacy, relish hearty Brunello di Montalcino wine and the sharp flavors of local cheeses, and hone your cooking skills with a Tuscan cooking demonstration. This Tuscan sojourn is sure to delight all of your senses!

Pricing from
Trip Type
Individual Travel Tour, International Land & Rail Voyages
Departure Dates
Jun 16, 2020 - Jun 24, 2020




  • day 1

    In Transit

    Depart for Florence, Italy

  • day 2

    Florence, Italy | Cortona

    Transfer to Cortona. Check in to the Villa Marsili. This evening, meet your fellow travelers during a Welcome Reception and Dinner at the villa.

  • day 3


    Discovery: The Tuscan Countryside. Travel through the Val d’Orcia, a patchwork of burgeoning hill country. Partake in a culinary experience at a family-owned winery in the Brunello di Montalcino region. Tour the winery and sample satisfying vintages and delicious local cheeses.
    Take pleasure in leisure time back in Cortona. Enrichment: Cortona and its Environs. Examine Cortona’s history and its relationship to Tuscany. Discovery: Walking Tour of Cortona. Admire Cortona’s artistic and historical treasures. As you stroll past historic palazzo, notice the village’s Etruscan features. Dwell in the Piazza della Repubblica and admire the town hall. Appreciate the façade of the Museo Diocesano, and discover soul-stirring vistas from the town’s ancient porta.

  • day 4


    Discovery: Siena. Siena claims a lofty perch atop three hills. See the architecture surrounding the Piazza including the 14th-century Torre del Mangia, the Piazza Chapel and the Civic Museum. Then step into a true masterpiece of Italian Romanesque-Gothic architecture when you visit the Duomo, home to fascinating works of art and sculpture.
    Free Time: Craft your own itinerary at leisure.
    Meander along Siena’s winding cobblestones, or climb to the top of the Torre del Mangia. Enrichment: Renaissance Art. Discuss various influences that shaped the art of the Renaissance. Gather for an authentic Italian dinner.


  • day 5


    Discovery: A Taste of Umbria in Orvieto.
    Encounter this quaint hilltop town while exploring its charming piazzas and winding lanes. Visit the village’s immense cathedral decorated with dazzling golden mosaics, and relish colorful panoramas highlighting Umbria’s rolling hills and lush countryside.
    AHI Connects: Olive Oil. Tour a family-owned olive oil farm outside of Orvieto. The property features an insightful museum that showcases the region’s rich agricultural traditions. Enjoy a delicious lunch and savor a tasting of the farm’s olive oil.

  • day 6


    Enrichment: Contemporary Italy. Learn about Italy’s place in the European Union and its modern-day political, economic and social status.
    Discovery: Montepulciano. Travel through the Val di Chiana to the ancient Etruscan city of Montepulciano. En route to this walled-in city, pause at the bottom of the hill for a visit to the Church of the Madonna di San Biagio. Consecrated by Pope Clement VII in 1529, the church features large arches and bell towers. In Montepulciano, walk with your group up to Piazza Grande, located at the city’s highest point. Known as the village’s social center, the square features the Palazzo Comunale, or town hall, which boasts a soaring clock tower.
    Free Time: Enjoy leisure time in Montepulciano.
    Stroll from the Piazza Grande to the bottom of the hill. Along the way, chat with artisans in their workshops and peek into centuries-old wine cellars.
    Dine on classic Tuscan cuisine for lunch. Free Time: The remainder of your evening is at leisure in Cortona to make your own discoveries.

  • day 7


    Discovery: Tour of Assisi. Encounter magnificent Assisi. Visit the Basilica of San Francesco, which is dedicated to St. Francis, and step inside the Basilica of Santa Maria degli Angeli. Have time for lunch at your leisure before departing Assisi.

  • day 8


    Discovery: Museum of the Etruscan Academy.
    Visit the 14th-century Praetorian Palace and discover archaeological finds and important Etruscan, Greek, Roman and Egyptian works of art, plus see mosaics and collections of engraved gems.
    AHI Connects: Tuscan Cuisine. Savor the sight, smells and flavors of Tuscan cuisine today as you watch a cooking demonstration. Then celebrate your new knowledge while enjoying lunch.
    Tonight, gather with your fellow travelers for a Farewell Reception and Dinner at the villa.

  • day 9

    In Transit

    Transfer to the Florence airport for the return flight to your gateway city.

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