Tour with Private Wine Tastings, Meals Featuring Regional Specialties, and Cultural Side Trips

In central Italy, the regions of Umbria and Tuscany are known for their medieval towns, rolling countryside, and wines—both the brunello and orvieto classico call this area home. You’ll get a chance to sample these as well as other local wines and regional specialties during the five-day, four-night luxury Italian food-and-wine tour from Ciao Andiamo, a tour company that earned praise from Newsday for its focus on small, family-run businesses. Each tour is limited to eight people to ensure each participant receives personalized and attentive service.

The culinary tour includes four nights of luxury accommodations, some meals, and daily excursions that delve into the region's food and wine. Each tour also includes a special culinary experience that changes each season: autumn travelers might visit an olive grove for an olive-oil pressing and tasting, whereas springtime excursions visit an Old-World bread-making factory. View the full itinerary here. Three-day post-trip extensions and other add-ons are available for an additional fee.

Day 1: You’ll be picked up in Rome to make the 1.5-hour drive north to Orvieto, a city in southwestern Umbria famous for producing orvieto classico, a dry white wine made from five grape varietals. Here, visit a local winery to taste several Umbrian wines with a spread of cheeses and bruschetta. Then it’s on to the Hotel Palazzo Bocci in Spello, about 60 miles (96 km) northeast, where you’ll settle into double rooms. Due to availability, a similar four-star hotel in the region may be substituted if necessary. That night, the tour heads into the city for a dinner of tagliatelle with cheese and black peppercorns, oven-roasted lamb, black-truffle frittata, and other classic Umbrian dishes.

Day 2: In the morning, the group will drive about 90 minutes to Cortona for a private tour of the centuries-old Fortress of the Girifalco and Museo Etrusco, where you’ll see ancient artifacts from the Etruscan civilization. You’re on your own for lunch, but you can stop at a local trattoria to sample dishes flavored with regional olive oils, black truffles, and sheep’s-milk cheeses. After visiting a goldsmith workshop, you’ll get an exclusive visit at Braccesca dei Marchesi Antinori, a local winery that’s closed to the general public.

Day 3: A full-day, private trip into Tuscany brings you to the towns of Pienza and Montalcino—known for pecorino cheeses and brunello wines, respectively—as well as Montepulciano, where you’ll taste wines and antipasti at one of the region’s oldest wineries. At sunset, the group will head to a local farm for a hearty dinner.

Day 4: In the morning, you’ll learn to create classic Umbrian cuisine during a family-run cooking class, and then eat your handiwork for lunch. That afternoon, the group heads 30 minutes south to tour Spoleto, a medieval city best known for storied basilicas (one dates back to the fourth century) and the Tower's Bridge constructed of 10 stone arches. In the evening, you’ll return to Cortona for country-style pizza served in a family home—a quintessential Italian experience.

Day 5: The drive back to Rome includes a stopover in Montefalco, where you’ll have lunch with regional wines, as well as a visit to Cascata delle Marmore, the world’s tallest manmade waterfall, created by the ancient Romans.