Day 1 – Sunday, September 19 | Overnight Flight

Depart on an overnight flight to Florence. Relax and look ahead to vineyards, stone villages, and Tuscan flavors waiting just beyond the horizon.

Day 2 – Monday, September 20 | Florence • Siena • Tuscan Countryside

Arrive in Florence and travel into Tuscany, stopping in Siena for lunch and a guided walking tour of the historic center and Piazza del Campo. Continue to Le Terre dei Cavalieri Agriturismo, where Marco Lori welcomes you with wine and a festive welcome dinner. (D)

Day 3 – Tuesday, September 21 | Cortona & Countryside Cooking

Enjoy breakfast overlooking rolling fields before a hands-on cheese-making and cooking class at Fattoria Bistecca, followed by a farm lunch with wine. Visit the hill town of Cortona for a guided introduction and free time to explore. Evening at leisure back at the agriturismo. (B, L)

Day 4 – Wednesday, September 22 | Lake Trasimeno & Isola Maggiore

Travel to Passignano sul Trasimeno and ferry to Isola Maggiore, where lace-making traditions endure. Enjoy a lakeside fish lunch, then continue to Castiglione del Lago. Return to the resort for a private food and wine pairing dinner hosted by Marco. (B, L, D)

Day 5 – Thursday, September 23 | Montepulciano & Olive Oil Traditions

Visit Frantoio Burraschi to learn the craft behind Tuscan olive oil. Continue to Montepulciano for free time before touring the atmospheric De Ricci wine cellars. Enjoy a small-plates dinner paired with Marco’s selected wines. (B, D)

Day 6 – Friday, September 24 | Arezzo & Villa La Ripa Winery

Discover the art of prosciutto-making at Pratomagno Prosciutti, then explore Arezzo with time for lunch and browsing. This evening, enjoy a private tour and tasting at Villa La Ripa winery. Dinner on your own. (B)

Day 7 – Saturday, September 25 | Perugia & Tuscan Cooking Class

Visit a Perugia chocolate factory and browse the vibrant Pian di Massiano Market. Back at the agriturismo, take part in a hands-on cooking class using market-fresh ingredients, followed by a celebratory dinner of your creations. (B, D)

Day 8 – Sunday, September 26 | Brunello, Montalcino & Pienza

Travel through vineyard country to Fattoria dei Barbi for a Brunello tasting and traditional lunch. Enjoy free time in Montalcino, then visit Pienza, a UNESCO World Heritage Site. Farewell dinner this evening hosted by Marco. (B, L, D)

Day 9 – Monday, September 27 | Florence Highlights

Return to Florence for a guided city tour featuring reserved entry to Michelangelo’s David and the Duomo. Enjoy lunch and free time to explore before checking into your hotel. Evening at leisure. (B, L)

Day 10 – Tuesday, September 28 | Departure

Transfer to the Florence airport for your flight home, carrying memories of Tuscan flavors, sunsets, and shared moments. (B)