Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns (Rome to Tuscany) (2025)

Begin your Italian adventure in the historic city of Rome. From there, journey through the picturesque regions of Umbria and Tuscany, discovering their endless treasures. Immerse yourself in the rich culture, history, and culinary delights that these regions have to offer.

Spend the day exploring Rome, Italy's dynamic capital city. Immerse yourself in the local culture and kick-start your journey with a delicious welcome dinner, offering a taste of the city's vibrant culinary scene.

Travel to the charming hill town of Spoleto in Umbria. Explore its historic streets with a local expert, marvel at the architectural wonders of the Rocca Albornoz castle and the Duomo of Santa Maria Assunta. Visit a family-owned olive presser and learn about the oil-making process before tasting the exquisite extra virgin olive oil produced there.

Journey to Assisi, the birthplace of St. Francis. Embark on a walking tour of the old city with a local guide, learning about its rich history. Visit the famous Basilica of St. Francis and enjoy a delightful lunch at a local family's country home, making friends and sharing stories.

Experience the epicurean side of Umbria. Join a local truffle hunter and his trained dogs in search of the elusive fungi in the shadow of the Apennines. Savor the taste of freshly found truffles during a rustic, home-cooked lunch before returning to your hotel in the late afternoon.

Leave Umbria and head to the picturesque villages of Tuscany. Taste the region's prized pecorino cheese at a local dairy farm and enjoy the serene views of the Val d'Orcia region. Arrive in Pienza, a UNESCO-listed Renaissance village, and spend the evening exploring the local scene.

Embark on a culinary journey through the Orcia Valley. Visit an artisanal pasta factory, explore the unique hamlet of Bagno Vignoni, and tour a winery in Montalcino. Indulge in a multi-sensory tasting, pairing wine with music. Spend the afternoon at leisure in Pienza, perhaps exploring the countryside along the white roads that cut through the farmland.

Take a guided walking tour through Siena, delving into the local history and learning about the world-renowned Palio Horse Race. Enjoy free time to explore more of this hilly town. An afternoon drive through Tuscany's Chianti Region takes you to your hotel, a beautifully restored Tuscan villa.

Explore Florence, the 'Cradle of the Renaissance,' during an extensive walking tour with a local expert. View the iconic Ponte Vecchio, the imposing Palazzo Vecchio, and the richly adorned Piazza del Duomo. Enjoy some free time to discover the city's endless treasures before returning to your Tuscan villa in the evening.

Spend your morning in San Gimignano, a town renowned for its 13th-century medieval towers. Enjoy authentic Italian gelato from an award-winning parlor as you wander the cobbled streets. Return to your hotel mid-afternoon and gather with your fellow travelers for a farewell dinner of Tuscan specialties as the sun sets.

Your journey through Tuscany and Umbria comes to a close today. Spend your final moments soaking in the serene beauty of your restored Tuscan villa, reminiscing about the unforgettable experiences of the past 10 days.