Experience Italy Like A Local

Depart the USA for arrival at Rome FCO before 9am, you will be met and chauffeured through the Tuscan countryside to the Buccelletti Estate in Castiglion Fiorentino. Upon arrival, you will be personally welcomed by the Buccelletti family and escorted to your fully stocked private villa, where you may unwind and settle in before the evening’s Welcome Dinner.

As the sun sets, enjoy an elegant al-fresco dining experience featuring refined local cuisine thoughtfully paired with wines from the Buccelletti cantina—an unforgettable introduction to Tuscany and the days ahead.

After a leisurely breakfast buffet, enjoy a guided tour of the Buccelletti Estate, including the olive mill and wine-processing rooms. Throughout the visit, you’ll taste fine estate wines while learning the rich history of this storied family and their deep roots in the region.

Following the tour, gather for lunch before returning to your villa for a relaxed afternoon—unwind by the pool, enjoy the hot tub, or simply take in the sweeping Tuscan views.

In the late afternoon, depart for the historic walled city of Cortona, where you’ll enjoy time for sightseeing and shopping before dinner at Logetta, set against one of Tuscany’s most iconic backdrops.

After breakfast, set out on a full-day Val d’Orcia excursion, beginning with visits to the Montepulciano wine region. Enjoy a guided winery tour and tasting, paired with traditional local Tuscan products that highlight the flavors of the region.

The journey continues to Pienza, the celebrated Renaissance hill town, where you’ll visit an organic cheese farm to learn how the world-famous Pecorino is produced. The experience concludes with a memorable lunch served from one of the valley’s most breathtaking vantage points.

Following lunch, spend time exploring the medieval center of Pienza at your leisure—browse artisan shops, wander the cobblestone streets, and indulge in gelato before returning to the estate.

In the evening, gather back at the villa for a relaxed pizza party, featuring estate wines and local charcuterie—an easy, convivial close to a day immersed in the heart of Tuscany.

This day is yours to enjoy at your own pace, with a selection of optional excursions available—private winery visits, natural hot springs, guided hiking or biking experiences, or even a private cooking class hosted in your villa.

In the evening, gather for dinner at the world-famous Da Muzzicone, where the highlight of the meal is the legendary house-made pasta Umbilici—a dish with a storied, secret past—paired with a classic Tuscan ribeye, delivering an unforgettable culinary finale.

Travel by local train to Florence for a guided culinary walking tour that eats and drinks its way through one of the world’s most iconic cities. Along the way, you’ll receive a curated tote bag and detailed maps highlighting the day’s stops, as well as select partner shops offering exclusive discounts to explore at your leisure.

Iconic landmarks such as Michelangelo’s David, the Ponte Vecchio, and the Duomo will be within reach as you experience Florence through its food, wine, and culture. At the Mercato Centrale, enjoy a memorable lunch at a Michelin-starred restaurant, featuring one of Florence’s historic wine windows—an authentic and rare Tuscan tradition.

In the evening, return to the Buccelletti Estate, where an elegant al-fresco pasta dinner awaits, showcasing local delicacies prepared by award-winning chefs—bringing the flavors of Florence back to the tranquility of the Tuscan countryside.

After breakfast, depart for the Chianti wine region, where you’ll explore exceptional wines from local producers, visit picturesque hillside towns, and enjoy a leisurely lunch along the way.

On the return journey, stop in the spiritual medieval village of Monteriggioni, a remarkably preserved walled town that offers a glimpse into Tuscany’s storied past.

In the evening, enjoy a curated wine-pairing dinner at the Buccelletti Estate, weather permitting. Alternatively, dinner will be hosted in the nearby town of Sinalunga, offering another opportunity to savor the flavors of the region.

Your final full day before departing for Rome is yours to enjoy at a leisurely pace. Private drivers can be arranged for visits to nearby towns such as Perugia or Assisi, or for a relaxing excursion to the region’s natural hot springs. Alternatively, the train to Arezzo offers an easy fifteen-minute ride, inviting you to explore a vibrant local city at your own pace.

On our final evening together, gather for a truly special farewell—an intimate dining experience set among the vineyards, celebrating the journey, the friendships formed, and the flavors of Tuscany.

Early in the morning, depart for Rome’s airport for your return journey. A thoughtfully prepared breakfast to-go will be provided, with direct drop-off at the terminal for a seamless departure.

For those wishing to extend their stay, additional nights in Rome may be arranged for an additional fee. As always, we are happy to assist in curating accommodations and bespoke experiences throughout Rome for guests who choose to continue their journey.