Tour begins: 6:00 PM, Villa La Massa. A transfer is included from Florence's Peretola Airport to Villa La Massa in Candeli on the outskirts of Florence, set at the gateway of the Chianti wine region in Tuscany. Meet your fellow travelers at a welcome reception and dinner tonight at your historic luxury hotel – a former 16th-century Renaissance estate of the Medici family on the banks of the Arno River, surrounded by 22 acres of gardens, olive groves and lemon trees.

Chianti, one of the oldest wines in the world, has been produced in Tuscany since the ancient Etruscans tended their vineyards here 2,500 years ago. Imagine its long-lived history as you drive through the Chianti countryside this morning to a farmhouse cooking school in the ancient Tuscan village of Montefiridolfi. This morning's hands-on cooking class with the former head chef of a Michelin-starred restaurant introduces you to the tastes and traditions of its regional food through anecdotal stories that add more flavor to this immersive culinary experience. Enjoy a wine tasting of Antinori wines at their Fonte De' Medici agriturismo as well as a farm to table lunch.Wine tasting is on the menu during a farm to table lunch, then return to your hotel; join us for dinner tonight at a typical Tuscan restaurant.

Travel this morning to the ancient hilltop Tuscan city of Arezzo, whose long history predates the Roman Empire, going all the way back to the days of the Etruscans in the 4th and 5th centuries BC. Today a city of just under 100,000 people, Arezzo possesses a wealth of historic architecture spanning the 11th to the 19th centuries – some of which you'll see on a walking tour – including many piazzas, palaces, churches and basilicas, as well as a 16th-century Medici fortress (the Fortezza Medicea). After more time to explore and have lunch as you please in Arezzo, continue your journey to Lake Trasimeno and on into the province of Umbria. Arrive early evening at your hotel in Gubbio, set in a 17th-century stone monastery overlooking wooded hills, and enjoy dinner there at your leisure tonight.

Note: On tours of May 29; September 6, 13; October 4 and 11, guests will have an alternate itinerary for day 3 featuring an opportunity to meet Author Frances Mayes (Under the Tuscan Sun) in her adopted home town of Cortona, Italy, for a talk on her life in Italy over the last 30 years. In addition to a guided walking tour of Cortona with a local historian and guide, you'll attend a fine dining lunch prepared by a Michelin star chef featuring local wine.

Explore medieval Gubbio on a walking tour this morning with a local guide. View the town's well-preserved Roman amphitheatre still in use today, its 13th-century church of Sant'Agostino, adorned with spectacular frescoes, and the turreted tower of Palazzo dei Consoli, built between 1332-1349. Spend some time discovering more of Gubbio on your own, including its many craft boutiques known for their pottery and ceramics. The "black diamonds" of Umbria, truffles, known as tartufi in Italian, are mushrooms so rare and unique-tasting that they can cost hundreds, if not thousands, of dollars per pound. Enjoy a precious taste of these subterranean delicacies during lunch in a charming renovated castle on a truffle farm... then sniff them out on a private truffle-hunting experience in the Umbrian woods with an experienced guide and his trained dog who lead you to the prize! The evening is free to enjoy as you wish in Gubbio.

A UNESCO World Heritage Site, Assisi reigns over Umbrian landscapes atop a hilltop perch that has welcomed travelers for centuries, especially pilgrims in search of heaven-sent miracles from St. Francis, who was born here. A guided walking tour of this medieval gem includes visits to the Basilica of San Francesco, eternal resting place for its patron saint, adorned with 13th-century frescoes by Giotto depicting the life of St. Francis and other works from the medieval and Renaissance periods. A Tauck-Exclusive al fresco lunch in the vineyards of Lungarotti Winery ensures an unforgettable taste of the bounty of land and vine in Torgiano (weather permitting). Continue on this afternoon to Umbria's capital city, Perugia, once one of the key cities of the Etruscan civilization. Your hotel for the next two nights is located in the historic heart of Perugia, where your evening is free.

Your day begins with a guided visit of Perugia; from your hotel walk down Corso Vanucci to the main fountain; tour the square and inside visit of the Collegio del Cambio, home to remarkable frescoes. Enjoy some free time to explore as you wish, or join us for a short drive to the nearby workshop of Giuditta Brozzetti, housed in the former Church of San Francesco. Inspired by the women's tradition of producing the necessary materials for the household, Brozzetti sought out Umbrian traditional designs and in 1921 founded this workshop / school. One of the few remaining ateliers of hand-weaving on antique "Jacquard" frames in Italy, it is known for its unique characteristics typical of medieval Perugia. Tonight you have a choice of dining at your hotel's restaurant or a local taverna.

You may be familiar with the saying that "all roads lead to Rome." Today they do just that with a few stops along the way. From Perugia drive to Spoleto for a guided tour of the city. Famous for the Ponte Delle Torri (Bridge of Towers) erected in the 14th century on the foundations of a Roman aqueduct, the bridge is 262 feet high and 755 feet across and built with an impressive set of 10 arches. See the bridge, visit the 12th-century Duomo of Spoleto and spend some free time in town, enjoying lunch as you please in Spoleto before traveling to Narni for a fascinating afternoon of exploration. Visit Narni Sotterranea (Narni Underground), the ancient Roman ruins which lay hidden underground for centuries until six young speleologists on a caving expedition rediscovered them in a vegetable garden in 1979. Hear all about the infamous tales that led to this hidden archaeological find as you discover a 12th-century chapel covered in frescoes, secret tunnels leading under the monastery complex of San Domenico, a Papal inquisition torture chamber and a prison cell covered in cryptic graffiti. Then drive on to Rome, arriving late afternoon for an overnight stay; join us for a farewell reception and dinner tonight.

Tour ends: Rome. Fly home anytime. A transfer is included from Hotel Indigo St. George to Leonardo da Vinci Airport in Fiumicino or Rome Termini Train Station. Allow three hours for flight check-in at the airport.