This tour starts Spoleto, Italy and ends in Volterra, Italy.

3 nights in SPOLETO: Meet me in Spoleto, one of the most beautiful hilltowns in Umbria. With my expert local friend, we’ll discover the remnants of its Roman, Lombard, and Renaissance history, including its gorgeous cathedral and towering 800-year-old bridge. On a truffle hunt we’ll follow the dogs to unearth this delicacy, then enjoy it in our dinner. You’ll have free time to explore the crooked lanes (with moving sidewalks that let you skip some of the steepest stretches), hike or bike through the forest, or just relax in a cozy trattoria.

3 nights in ASSISI: The hometown of St. Francis is imbued with peacefulness. We’ll join a fantastic Umbrian guide to tour the medieval streets and the basilica with its art-history-making frescoes. At a family-owned winery, we’ll tromp through the autumn-tinted vineyard and enjoy a tasting with the charming winemaker herself. We’ll have a meal of local ingredients with a new twist at my favorite restaurant in town; in the tranquil countryside, we’ll savor a traditional “zero-kilometer” dinner and “la dolce far niente”--the sweetness of doing nothing. In your afternoons off, you could visit a spa, climb up to the fortress, or make your own pilgrimage to more sacred sites

3 nights in the SIENA area: En route to our next destination, let’s stop to explore remarkably well-preserved and relatively undiscovered Gubbio. Our local expert will bring its long history to life–from its pre-Etruscan version of the Rosetta Stone, to its Roman theater, to its medieval churches and their Renaissance art. Feeling brave? Join me on the “birdcage” chairlift for bird’s-eye views. In Siena, there’s always more to discover. My passionate local friend will lead us to corners many tourists don’t find, and will share firsthand stories of the excitement and rivalries of the famous Palio horse race. We’ll climb up to the cathedral’s rooftop to admire angelic views across the Tuscan hills. You’ll have plenty of time to relax over a coffee or glass of wine while people-watching on Europe’s finest piazza.

3 nights in the VOLTERRA area: Colle di Val d’Elsa, an untouristed town not far away in Tuscany, is a sweet surprise. Its walled center stretches along a ridge, the main street lined with medieval palazzi. Colle is famous for its crystal production and we’ll learn about its long history (since the 1300’s!) in the crystal museum. In remarkable plateau-topping Volterra, my brilliant local friend will share fascinating stories of the town’s Roman, Etruscan, and WWII eras, and watch an artisan at work on its beautiful alabaster. On our last evening together, we’ll toast our new friends over a harvest feast.

Optional FLORENCE 3-night extension: Even if you’ve come to Florence before, consider joining me to discover more of this world-class city’s sights, neighborhoods, and food. My favorite local guides will teach us about life in the Renaissance–and what it’s like to live in the city today. We’ll get hands-on experience with a working artist, and we’ll have a Tuscan cooking class with a friendly chef. My restaurateur friends will welcome us with seasonal fare in their cozy spaces, concluding our time together with more soul-satisfying meals together.

Itinerary subject to change.