Day 1: Overnight Flight
Board your overnight flight to the Italian capital of Rome.

Day 2: Rome, Italy - Tour Begins
Meet your fellow travelers in Rome for a welcome dinner in a local restaurant • Join in an interactive and fun presentation on Italy’s wines given by the restaurant’s sommelier • Indulge in a traditional 4-course meal, paired with some of the country’s finest wines.

Day 3: Rome - Orvieto - Umbria
Depart Rome • Travel to the Etruscan hill town of Orvieto, known for its white wine and Gothic cathedral housing a Signorelli fresco • Take time for a leisurely lunch or explore this town on your own • Spend the next four nights in a palace in the pristine Umbrian town of Trevi.

Day 4: Umbria - Spoleto - Cooking Class - Umbria
Embark on a guided walking tour of historic Spoleto • See medieval palaces, the ornate Duomo of Santa Maria Assunta, and the magnificent Ponte delle Torri, an aqueduct dating back to the 13th century • Enjoy free time to peruse the town’s shops and cafes • Pay a visit to a country restaurant housed in a 16th century farm house • The chef here provides a hands-on Umbrian cooking lesson • Indulge in an early dinner in the countryside.

Day 5: Umbria - Olive Oil Factory - Norcia - Montefalco - Umbria
Explore Umbria’s specialty food items through a series of tastings • Start the day with a visit to a local olive oil factory in the area of Trevi • Travel to Norcia, where skilled butchers have been handcrafting salumi for centuries • Taste some of their sausages and pecorino cheeses during a guided walking tour • Visit the basilica of St. Benedict • Stop off in Montefalco, nicknamed the Balcony of Umbria • Visit a local café to sip some of this region’s most prized wine, the Sagrantino.

Day 6: Umbria - Assisi - Cortona - Umbria
Travel to the walled city of Assisi • Enjoy a guided tour of the old city • See the Basilica dedicated to St. Francis, founder of the Franciscan order of monks • Experience this spiritual locale at your own pace • Later, continue to Cortona, the Etruscan town made famous in the film Under the Tuscan Sun • Enjoy a stroll around town, followed by a Tuscan dinner in one of Cortona’s historic locandas.

Day 7: Umbria - Siena - Monteriggioni - Tuscany
Travel to the city of Siena • Enjoy a walking tour and visit the historic piazza famous for the Palio Horse Race • Continue to the walled town of Monteriggioni for a stroll along quaint streets • Take a coffee break and try some Tuscan pastries before travelling to the town of Montaione • Make yourself at home in Tuscany for the next four nights.

Day 8: Tuscany - Florence - Tuscany
Set out on a short journey to Florence, “cradle of the Italian Renaissance” • Begin your day with a guided walking tour of the city sights, including the cathedral of Santa Maria Del Fiore, located in the religious center of the Piazza Del Duomo and the Palazzo Vecchio • Join your local guide in exploring the unique qualities of the city • Focus on Florence’s local artisans and visit their workshops • Spend some free time shopping and investigating Florence on your own • Return to Montaione.

Day 9: Tuscany - Winery - Montepulciano - Tuscany
Travel through southern Tuscany • A winery visit showcases the wine cellar, family estate, vineyards, olive groves and stunning views • The winery’s chef prepares an authentic Tuscan lunch, expertly paired with wines produced on site • Explore the town of Montepulciano before returning to Montaione.

Day 10: Tuscany - San Gimignano - Volterra - Tuscany
Spend your morning in San Gimignano, known as the "Medieval Manhattan" • Look for the town's fourteen medieval towers that date back to the 13th century • Enjoy a stroll along Piazza del Duomo and Piazza della Cisterna • Travel to Volterra, a former Etruscan city which sits high above the Tuscan countryside • Visit one of the most famous Etruscan museums in Italy, the Guarnacci Museum • Enjoy a farewell dinner with your fellow travelers.

Day 11: Tuscany - Tour Ends
Your vacation comes to a close in Montaione.