Day 1 – Depart for Italy

Your adventure begins with an overnight flight to Florence. Rest and dream of golden vineyards, stone villages, and the warm Tuscan light that awaits.

Day 2 – Siena and Arrival in Tuscany

Arrive in Florence and travel through the Tuscan countryside to the medieval city of Siena. Enjoy lunch in the historic center and a guided walking tour of its Gothic architecture and famous Piazza del Campo. Continue to Le Terre dei Cavalieri Agriturismo, your countryside retreat for the week. You’ll be greeted by Marco Lori, Italian Sommelier and Master Winemaker, who welcomes you with wine and true Tuscan hospitality. Gather this evening for a delicious welcome dinner and introduction to the flavors of Tuscany. (D)

Day 3 – Cheese Making and Cortona

Wake to peaceful countryside views before visiting Fattoria Bistecca for a hands-on cheese-making and cooking class. Enjoy your creations over a rustic farm lunch paired with local wine. In the afternoon, explore the hill town of Cortona, filled with cobbled streets, Renaissance churches, and panoramic views. Return to the agriturismo for a relaxed evening — swim in the pool, stroll the gardens, or sip Chianti beneath the stars. (B, L)

Day 4 – Lake Trasimeno and Food & Wine Pairing

Travel to Passignano sul Trasimeno, a lakeside gem where you’ll ferry to Isola Maggiore to discover its lace-making heritage. Enjoy a lakefront lunch featuring freshly caught fish, then continue to Castiglione del Lago, one of Tuscany’s most scenic hill towns. Back at the resort, unwind before an exclusive wine-pairing dinner hosted by Marco, where he connects each wine to the landscapes you’ve explored — a storytelling experience through flavor. (B, L, D)

Day 5 – Olive Oil and Montepulciano

Visit Frantoio Burraschi to learn how olives become Tuscany’s “liquid gold.” Continue to Montepulciano, famed for its Renaissance architecture and rich Vino Nobile wines. Explore at leisure, then descend into the atmospheric De Ricci cellars for a private tasting. Return to the resort for a small-plates dinner paired with Marco’s hand-selected wines — an evening celebrating history, hospitality, and the art of slow living. (B, D)

Day 6 – Prosciutto, Arezzo, and Villa La Ripa

Discover the craft behind Italy’s beloved prosciutto at Pratomagno Prosciutti, then explore the artistic city of Arezzo, known for frescoes and charming piazzas. This evening, visit Villa La Ripa, a stunning villa winery, for a private tasting. Return to the resort for a relaxed evening — dinner on your own, perhaps in Cortona, or quiet time under the Tuscan night sky. (B)

Day 7 – Perugia and Cooking Class

Today begins with a visit to a Perugia chocolate factory, followed by the lively Pian di Massiano Market filled with fresh produce and local specialties. Back at the agriturismo, join a hands-on cooking class using your market finds. Together, prepare a Tuscan feast — shared laughter, local wine, and the joy of cooking make this evening unforgettable. (B, D)

Day 8 – Brunello and Farewell Dinner

Travel through vineyard-draped hills to Fattoria dei Barbi, where Brunello wines have been crafted for generations. Enjoy a traditional lunch paired with their finest vintages, then continue to Montalcino for free time to explore. Visit Pienza, a UNESCO World Heritage town known for its pecorino cheese and Renaissance beauty. Tonight, celebrate with a farewell dinner hosted by Marco, raising a glass to new friendships and unforgettable moments. (B, L, D)

Day 9 – Florence and the Renaissance

Bid farewell to your Tuscan retreat and travel to Florence, the Renaissance capital. Enjoy a guided city tour including reserved entry to Michelangelo’s David and the breathtaking Duomo. After lunch, enjoy free time to shop, explore museums, or simply soak in the city’s beauty. Check into your Florence hotel and enjoy the evening at leisure. (B, L)

Day 10 – Departure

After breakfast, transfer to the Florence airport for your flight home. Return with fine wines, olive oils, and the richer treasures of Tuscany — laughter shared, sunsets savored, and the warmth of Marco’s hospitality. (B)