Itinerary

1. Overnight Flight

   On a journey through Italy’s roads less traveled, discover its endless treasures from Rome to Umbria to Tuscany, and the marvels of wine, cuisine, culture, and history in between.

   Accommodation: Hotel Antica Dimora Alla Rocca, Trevi

2. Rome, Italy - Tour Begins

   Italy’s dynamic capital city beckons. Get a taste of the local culture and start your journey at a delicious welcome dinner.

   Meal included: Dinner
   Accommodation: Hotel Antica Dimora Alla Rocca, Trevi

3. Rome - Spoleto - Umbria

   Olive and cypress trees accent the Etruscan hill town of Spoleto. Stroll the historic streets with a local expert and see centuries of architectural history, from the Ponte delle Torri aqueduct to the gilded elegance of the Duomo of Santa Maria Assunta. Continue to discover Spoleto on your own this afternoon. Eat, drink, and explore the local scene. Then take in the splendors of country life in a pristine Umbrian hill town, your home for the next 3 nights.

   Meal included: Breakfast & Dinner
   Accommodation: Hotel Antica Dimora Alla Rocca, Trevi

4. Umbria - Assisi - Umbria

   Travel to Assisi, birthplace of St. Francis. Set out on a walking tour of the old city with a local guide, learning about its history as you stroll the medieval streets. Visit the famous Basilica of St. Francis. Later, a local family welcomes you to their country home for lunch as their honored guest. Share stories and make an Umbrian friend (or two).

   Meal included: Breakfast & Lunch
   Accommodation: Hotel Corsignano, Pienza

5. Umbria

   In the shadow of the Apennines, embark on a culinary journey through the dense olive groves of Umbria to an award-winning frantoio (olive presser), where olives are pressed each November.* After learning about the many varieties of trees and oil-making methods, join a tasting of the different kinds of EVOO produced at the mill. Your exploration of Umbria’s gastronomy continues with a visit to an artisanal factory where the same family has been producing pasta since 1918. After touring their museum, learn about the production process during a factory visit.

   Meal included: Breakfast
   Accommodation: Hotel Corsignano, Pienza

6. Umbria - Pienza

   Leave Umbria for the villages of Tuscany, nestled among the rolling hills and cypress trees of the Val d’Orcia region (UNESCO). Taste the flavors of the region at a local pecorino cheese farm. Snack on some of the cheesemaker’s creations and take in the views of the sparse farmhouses and open fields on your way to Pienza (UNESCO), a Renaissance village where flowers and plants adorn the cobblestoned streets.

   Meal included: Breakfast & Lunch
   Accommodation: Villa San Lucchese Hotel, Chianti Countryside

7. Pienza

   Traverse the Tuscan countryside to the unique hamlet of Bagno Vignoni, whose central piazza is filled with thermal water once used to cure pilgrims who stopped here on their way to Rome. Then explore hilltop Montalcino, namesake to one of Italy’s great red wines, the Brunello. Tour a winery’s estate and cellar before indulging in a multi-sensory tasting, pairing wine with music. Back in Pienza for an afternoon at leisure, maybe you’ll explore the countryside along one of the many white roads that cut through the farmland.

   Meal included: Breakfast
   Accommodation: Villa San Lucchese Hotel, Chianti Countryside

8. Pienza - Siena - Chianti Region

   Take a guided walking tour through Siena, delving into the local history as you learn about the world-renowned Palio Horse Race. Enjoy free time to explore more of this hilly town, perhaps visiting its cathedral or the town hall’s frescoes. An afternoon drive through Tuscany’s Chianti Region takes you to the restored Tuscan villa* where your hotel is located.

   Meal included: Breakfast
   Accommodation: Villa San Lucchese Hotel, Chianti Countryside

9. Chianti Region

   Explore Florence, the “Cradle of the Renaissance,” during an extensive walking tour in the company of a local expert. View the Ponte Vecchio, the only Florentine bridge to survive WWII. Take in the Palazzo Vecchio, where, for over 300 years, the Medici Family ruled over the city. Admire the Piazza del Duomo, richly adorned by polychrome marble and gilded bronze doors. Take some time on your own*** to explore the city’s seemingly endless treasures, before returning to your Tuscan villa in the evening.

   Meal included: Breakfast

10. Chianti Region

    Experience Tuscany’s epicurean side and join a local truffle hunter in search of the elusive fungi in company of his trained, truffle-sniffing dogs. Sample the goods yourself during a rustic, home-cooked lunch. Spend your afternoon in San Gimignano, whose beautiful 13th-century medieval towers stand tall over the surrounding vineyards. As the sun begins to set, gather with your fellow travelers for a farewell dinner of Tuscan specialties.

    Meal included: Breakfast, Dinner & Lunch

11. Chianti Region - Tour Ends

    Your journey through Tuscany and Umbria comes to a close today in your restored Tuscan villa.

    Meal included: Breakfast