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.

   Meals: Dinner
   Accommodation: Hotel Antica Dimora Alla Rocca, Trevi

3. Rome - Orvieto - Umbria

   Olive and cypress trees accent the Etruscan hill town of Orvieto. Stroll the historic streets with a local expert and visit the prominent Gothic cathedral to gaze at a remarkable Signorelli fresco. Continue to discover Orvieto on your own this afternoon. Eat, drink, and disappear into the local scene before taking in the splendors of country life in a pristine Umbrian hill town, your home for the next 3 nights.

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

4. Umbria - Spoleto - Olive Oil Mill - Umbria

   Medieval palaces command the foreground of ancient Spoleto. In the shadow of the Apennines, embark on a walking tour to see centuries of architectural history, from the Ponte delle Torri aqueduct to the gilded elegance of the Duomo of Santa Maria Assunta. Explore more of Spoleto on your own before learning about olive oil at a family-run frantoio (olive presser). Venture into a local restaurant in the Nera Valley, where you’ll enjoy a cooking class in a former 12th-century abbey. Dig in to your handcrafted meal for dinner.

   Meals: Breakfast & Dinner
   Accommodation: Hotel Corsignano, Pienza

5. Umbria - Assisi - Home-Hosted Lunch - 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).

   Meals: Breakfast & Lunch
   Accommodation: Hotel Corsignano, Pienza

6. Umbria - Pecorino Cheese Farm - Orcia Valley - 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.

   Meals: Breakfast & Lunch
   Accommodation: Villa San Lucchese Hotel, Northern Tuscany Countryside

7. Pienza - Bagno Vignoni - Brunello di Montalcino Winery - 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 the evening, maybe you’ll explore the countryside along one of the many white roads that cut through the farmland.

   Meals: Breakfast
   Accommodation: Villa San Lucchese Hotel, Northern Tuscany 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.

   Meals: Breakfast
   Accommodation: Villa San Lucchese Hotel, Northern Tuscany Countryside

9. Chianti Region - Florence - Chianti Region

   Explore Florence, the “Cradle of the Renaissance,” with a local expert on foot. Wander along the glittering storefronts on the Ponte Vecchio, where gold shops adorn the only Florentine bridge to survive WWII. You’ll also take in the Palazzo Vecchio, the Piazza della Signoria, and Santa Croce. Take some time on your own to explore the city’s seemingly endless treasures, both historic and modern. Return to your Tuscan villa in the evening.

   Meals: Breakfast

10. Chianti Region - San Gimignano - Chianti Region

    Choose** how to explore Tuscan landscape because it’s your choice! Join a local truffle hunter in search of the elusive mushroom and sample the goods yourself -OR- take to the countryside on an ATV adventure along winding dirt roads, followed with a taste of truffle bruschetta. 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.

    Meals: Breakfast & Dinner

11. Chianti Region - Tour Ends

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

    Meals: Breakfast