Tuscany and lesser-known Umbria are two of Italy’s most beautiful—and bountiful—regions. Sitting next to each other in the center of Italy, both boast cypress trees, olive groves, medieval hill towns, and vineyards galore. That said, both are also famous for their fantastic food and wine.
On this 11-day tour, you’ll soak up Rome’s passionate street culture and then travel to the laid-back Umbrian region to wander the cobbled lanes of Orvieto. You’ll ogle the medieval fortress in Spigeto and get an Umbrian cooking lesson inside of a 16th-century farmhouse. Next, you’ll be whisked to Montefalco and sip the region’s most prized wine, Sagrantino, and visit a family-run frantoio (olive presser). The beauty of Assisi will simply beguile you, and then it’s on to Tuscany’s Val d’Orcia region where more wine tasting awaits. Feast on Tuscan cuisine and world-class art in Florence, and then explore the charming Tuscan villages of Siena, Monteriggioni, San Gimignano, and Volterra.
Itinerary / 11 daysPLAN YOUR TRIP
DAY 1Night Flight to Rome
DAY 2Rome's Dolce Vita
Later, join the stylish aperitivo (pre-dinner drinks) crowd and then move on to meet your travel group over a delicious welcome dinner.
DAY 3Cinematic Umbria: Orvieto
In the afternoon, you’ll be free to wander solo. Eat, drink, and soak up the local culture with a glass of Pinot Nero in hand and a tartufo (truffle) on your fork. Take it in slowly, you’ll have the next four nights to embrace these rustic Umbrian splendors.
DAY 4Culinary Umbria: Spoleto
Few travelers get to experience a country restaurant nestled inside of a 16th-century farmhouse, but this evening, after exploring the farm’s herb garden and cheese-making process, you’ll join the restaurant’s chef for a hands-on cooking lesson and then dine in the countryside.
DAY 5Montefalco and Bevagna
Later, a local family will welcome you into their country home for a delicious homemade lunch. Prepare to make an Umbrian friend or two.
DAY 7Tuscany: the Val d’Orcia Region
In Tuscany, locals spend an inordinate amount of time talking about food and wine. Join the conversation during a tour of a local winery’s family estate and enjoy a Tuscan lunch, created by the winery’s chef and paired with the vineyard’s own wines. Afterwards, relax at a restored Tuscan palazzo.