Italy’s dynamic capital city beckons. When in Rome, start your journey at a welcome dinner. Stay: Hotel Kolbe (D)

Olive and cypress trees dominate the Etruscan hill town of Orvieto. Stroll the historic streets as a local expert points out the city’s many treasures and visit the prominent Gothic cathedral to gaze at a remarkable Signorelli fresco. Orvieto’s many faces are yours to uncover independently this afternoon. Eat, drink, and disappear into the local scene – perhaps with a glass of Pinot Nero or Sangiovese in hand. Spend the next four nights enveloped in the splendors of country life in a pristine Umbrian hill town. Stay: Hotel Antica Dimora Alla Rocca, Trevi (4 Nights) (B/D)

Medieval palaces dominate the foreground of ancient Spoleto. In the shadow of the Apennines, a walking tour through the city’s streets reveals centuries of architectural history, from the Ponte delle Torri aqueduct to the gilded elegance of the Duomo of Santa Maria Assunta. Have the pleasure of exploring Spoleto’s many shops and cafes during time on your own this afternoon. A visit to a country restaurant, sheltered inside a 16th-century farmhouse, is the Italy few get to experience. Stroll the herb garden (weather permitting), and learn how cheese is made on the farm. Your palate-expanding journey continues as you join the chef for a hands-on Umbrian cooking lesson. Afterward, enjoy an early dinner in the countryside. (B/D)

Explore the charming medieval town of Montefalco, and take a step back in time in the place they call the “Balcony of Umbria” – a moniker given to the town for its unobstructed views of the Umbrian countryside. Sagrantino is this region’s most-prized wine; head to a local winery to see why during a tasting before sampling a variety of authentic Umbrian dishes at lunch. In Bevagna, marvels of Roman and medieval archaeology and architecture highlight an impressive walking tour. Cap the day off learning about local olive oil at a family-run ‘frantoio’ or olive presser. (B/L)

Travel to Assisi, birthplace of St. Francis. Set out on a walking tour of the old city with a local guide. Come to know its history as you stroll the medieval streets, pausing along the way to see its famed Basilica of St. Francis. Later, a local family welcomes you to their country home for lunch as their honored guest. Share stories and make an Umbrian friend (or two). (B/L)

Time slows down among the sunflower-covered hills and villages of Tuscany’s Val d’Orcia region. Among the vineyards and olive groves of this UNESCO World Heritage site, tour a winery’s family estate and cellar before indulging in an authentic Tuscan lunch, created by the winery’s chef and paired expertly with the vineyard’s very own wines. Retire later to a restored Tuscan palazzo. Stay: UNA Palazzo Mannaioni, Montaione (4 Nights) (B/L)

Explore another age altogether on a locally guided walking tour of Florence, the “Cradle of the Renaissance.” Behold the Cathedral of Santa Maria del Fiore in the religious center of the Piazza del Duomo and the Palazzo Vecchio, and tap in to Florence’s creative side at a local artisan’s workshop. After, take some time on your own to explore the city’s bounty of treasures, both historic and modern. (B)

Medieval Italy at its most visually striking is in Siena. On a visit to the Piazza del Campo during your guided walking tour of the city, learn about the world-renowned Palio Horse Race – which the historic piazza plays host to twice each year. Then, it’s your choice! Explore Siena’s beautiful Gothic cathedral at your own pace -OR- join a guide and immerse yourself in local life in a contrada, one of many small, close-knit communities, each one unique with traditions all its own. In the walled town of Monteriggioni, wander its quaint streets, seemingly frozen in time. (B)

Country roads lead to the “City of Alabaster,” Volterra. A former Etruscan city, this walled town perched high above the countryside boasts a history that dates back to the 7th century B. C. Spend time inside the Guarnacci Museum, one of the oldest public museums in Europe, circa 1761. Delight in witnessing a live alabaster-carving demonstration at a local workshop. Travel later to the “City of Beautiful Towers,” San Gimignano. Below fourteen 13th-century medieval towers, stroll the Piazza del Duomo and Piazza della Cistema. Tonight, gather together for a farewell dinner paired with an entertaining interactive presentation on wine, delivered by the restaurant’s own sommelier. (B/D)

Your journey through Tuscany and Umbria comes to a close today in Montaione. (B)

Italy's dynamic capital city beckons. When in Rome, do as the Romans do - start your journey at a delicious welcome dinner. (D)

Olive and cypress trees accent the Etruscan hill town of Orvieto. Stroll the historic streets as a local expert points out the city's many treasures and visit the prominent Gothic cathedral to gaze at a remarkable Signorelli fresco. Discover Orvieto's many wonders independently this afternoon. Eat, drink, and disappear into the local scene – perhaps with a glass of Pinot Nero or Sangiovese in hand. Spend the next four nights enveloped by the splendors of country life in a pristine Umbrian hill town. (B/D)

Medieval palaces command the foreground of ancient Spoleto. In the shadow of the Apennines, a walking tour through the city's streets reveals centuries of architectural history, from the Ponte delle Torri aqueduct to the gilded elegance of the Duomo of Santa Maria Assunta. Explore Spoleto's many shops and cafes during time on your own this afternoon. Sit down to a once-in-a-lifetime meal inside a 16th-century farmhouse nestled in the Italian countryside. There, you can stroll the herb garden (weather permitting), and learn how cheese is made on the farm. Your palate-expanding journey continues as you join the chef for a hands-on Umbrian cooking lesson followed by your early dinner in the countryside. (B/D)

Explore the charming medieval town of Montefalco, and step back in time in the place they call the “Balcony of Umbria” – a name given to the town for its unobstructed views of the Umbrian countryside. Sagrantino is this region's most-prized wine; head to a local winery to see why during a tasting before sampling a variety of authentic Umbrian dishes at lunch. In Bevagna, marvels of Roman and medieval archaeology are the highlights of an impressive walking tour. Cap the day off learning about local olive oil at a family-run frantoio or olive presser. (B/L)

Travel to Assisi, birthplace of St. Francis. Set out on a walking tour of the old city with a local guide. Learn all about its history as you stroll the medieval streets, pausing along the way to see its famed Basilica of St. Francis. Later, a local family welcomes you to their country home for lunch as their honored guest. Share stories and make an Umbrian friend (or two). (B/L)

Time slows down among the sunflower-covered hills and villages of Tuscany's Val d' Orcia region. Among the vineyards and olive groves of this UNESCO World Heritage site, tour a winery's family estate and cellar before indulging in an authentic Tuscan lunch. Created by the winery's chef, this meal is expertly paired with the vineyard's very own wines. Retire afterwards to a restored Tuscan palazzo. (B/L)

Get at a glimpse at another age on a locally guided walking tour of Florence, the “Cradle of the Renaissance.” Behold the Cathedral of Santa Maria del Fiore in the religious center of the Piazza del Duomo and the Palazzo Vecchio, and tap in to Florence's creative side at a local artisan's workshop. After, take some time on your own to explore the city's bounty of treasures, both historic and modern. (B)

Siena is medieval Italy at its most visually striking. Take a guided walking tour of the city, and learn about the world-renowned Palio Horse Race, held twice a year at the historic Piazza del Campo. Then, it's your choice! Explore Siena's beautiful Gothic cathedral at your own pace -OR- join a guide and immerse yourself in local life in a contrada, one of many small, close-knit communities, each one unique with traditions all its own. In the walled town of Monteriggioni, wander its quaint streets, seemingly frozen in time. (B)

Country roads lead to Volterra, the “City of Alabaster.” A former Etruscan city, this walled town perched high above the countryside boasts a history that dates back to the 7th century B. C. Spend time inside the Guarnacci Museum, one of the oldest public museums in Europe, built in 1761. Witness a live alabaster-carving demonstration* at a local workshop. Travel later to the “City of Beautiful Towers,” San Gimignano. Stroll the Piazza del Duomo and Piazza della Cistema, and marvel at a skyline dotted with more than a dozen 13th-century medieval towers. Tonight, gather together for a farewell dinner paired with an entertaining interactive presentation on wine, delivered by the restaurant's own sommelier. (B/D)

Your journey through Tuscany and Umbria comes to a close today in Montaione. (B)