Arrival & Welcome to the Castle Florence → San Gimignano → Winery Visit → Castello delle Serre We’ll meet in Florence at LHP Hotel River, our designated departure point, and depart promptly at 11:30 AM aboard our private air conditioned coach. Our first destination is the postcard-perfect town of San Gimignano, famous for its striking medieval skyline and towering stone architecture. Once home to more than 70 towers built by noble families eager to display their wealth, only 16 remain today—still standing proudly over the Tuscan countryside. Stroll through charming cobblestone streets lined with artisan boutiques, ceramic shops, and art galleries… or climb a tower for panoramic views you’ll never forget. Afterward, we’ll head to our first winery experience, where we’ll enjoy a tour, a delicious lunch, and a guided tasting to begin our week in true Tuscan style. Later, we arrive at Castello delle Serre, your home for the next seven nights. Settle in, take in the magic, and join us for a welcome dinner prepared by the castle owners.

Chianti & a Legendary Estate Today we journey into the rolling vineyards of the Chianti region, a landscape straight out of a Renaissance painting— dotted with castles, monasteries, olive groves, and vineyards stretching toward the horizon. Along the way we’ll visit charming villages and learn the rich history behind Chianti’s winemaking legacy, before arriving at the spectacular Tenuta Arceno for an unforgettable property and cellar tour, followed by a special tasting lunch. Dinner will be enjoyed back at the castle tonight.

Val d’Orcia & Montepulciano Few places in the world feel as cinematic as the UNESCO-protected Val d’Orcia—a landscape of cypress-lined roads, golden fields, and hilltop towns that define Tuscany. Our day begins in the magical town of Pienza, where you’ll have time to stroll independently and take in its stunning views and charming streets. Next, we continue to Montepulciano, where history and wine are woven into every stone. Here, you’ll have the chance to visit the incredible underground wine cellars of a historic winery, followed by a guided tasting of Vino Nobile di Montepulciano and a leisurely lunch. Return to the castle for time to freshen up, then we head out again for dinner in a nearby town.

Truffle Hunting & Brunello Celebrations Today is a true highlight: a once-in-a-lifetime truffle hunting experience in the Tuscan countryside. We’ll arrive in the woods and learn the fascinating story of truffles—how they grow, why they’re so prized, and what makes them such a treasured delicacy in Italian culture. Then, we’ll venture into the forest alongside specialized truffle dogs and expert hunters to witness the excitement firsthand. After the hunt, we’ll head to a nearby winery for a special lunch featuring truffles from our own adventure, paired with internationally celebrated Brunello wines. We return to the castle in the afternoon to relax and freshen up before our farewell dinner, hosted at a wonderful local farm-to-table setting—a fitting celebration to end an extraordinary week.