Welcome to Chianti: Where Wine, History, and Heart Meet

Day 1

Arriving at Villa Gran Sogno. There's something magical about those first moments in Chianti. As our Mercedes curves through cypress-lined roads, we can't help but be amazed — vineyards roll out like waves, medieval villages dot the hillsides, and some of the world's finest wines are aging quietly in centuries-old cellars below. Home for the week is Villa Gran Sogno, and what a home it is! This beautiful stone building started life as horse stables back in the 1350s, but Mauro and Connie have transformed it into something special. Walking into the lounge, we're greeted by Mauro's signature "Ciao Bello!" and one of his famous bear hugs (trust me, they're legendary). He pours everyone a glass of Chianti, and we toast to the week ahead. Mauro's love for this region overflows as he shares stories of his Italian roots. "This isn't just land," he tells us with a spark in his eye, "this is a story of generations of winemakers." The evening finds us by the pool, overlooking gardens that would make any chef jealous. Mauro shows us around the raised beds — his pride and joy. "Everyone talks about 'farm to table,'" he says with a grin, "but we Italians, we invented it!" The gardens are bursting with tomatoes, eggplant, and peppers that'll be starring in tomorrow's meals. And because no Italian welcome would be complete without it, we wrap up with Aperitivo and Aperol Spritz. Looking at the smiles around me, I can already tell — this week is going to be something special.

Day 2

Truffle Hunting & Kitchen Magic. We awake to a view that belongs in "A Room with a View" — morning mist dancing over the vineyards as the sun peeks over the hillside. With coffee in hand (Italian, of course), we take a peaceful walk to the hilltop, soaking in the quiet countryside. Then the real adventure begins: Recardo and his talented dogs join us for a private truffle hunt in the nearby woods. Next up? It's time to channel our inner Italian chef! Mauro leads us through his vibrant garden, teaching us to pick ingredients with a practiced eye. "Cooking," he shares while guiding us through the art of pasta-making, "is about respect. Respect for ingredients, for tradition, and for the land." His stories about generations of Italian cooking have us laughing and learning in equal measure. The reward? Enjoying our handmade feast on the villa's terrace, overlooking the very grounds where our ingredients were picked. The afternoon takes us to what Mauro calls "the neighbor's house" — a charming 13th-century village where a fifth-generation family makes wine in Castellina. We watch Mauro and vineyard owner Sergio chat in rapid-fire Italian about Sangiovese grapes (or was it soccer? We're still not sure!). The highlight? Tasting wine straight from the barrel — each sip tells a story of sun, soil, and centuries of tradition. We cap off the day in the village of Castellina with dinner followed by two Italian essentials: gelato and passeggiata. As Mauro explains, passeggiata isn't just an after-dinner walk — it's about slowing down, enjoying life's simple pleasures, and yes, maybe having just a bit more gelato!

Day 3

Wine Wisdom & Liquid Gold. Today is special — we're meeting Mauro's friend Alessandro, a winemaking legend who's achieved what no other vintner has: two wines on Wine Spectator's Top 100 list. Over a five-course lunch at Vallepicciola (prepared by Alessandro's personal chef!), we sample exceptional vintages while Alessandro shares stories of triumphant harvests and challenging years. The afternoon finds us among ancient olive trees, their silver-green leaves shimmering in the light. We're lucky enough to catch the harvest, and Mauro walks us through the fascinating process of creating extra virgin olive oil. "This is liquid gold," he says, reverently tasting freshly pressed oil. "And those 91 trees over there? They're 150 years old — think of the history they've seen!" Dinner is something extraordinary. We head to Osteria di Passignano, tucked inside a historic abbey complex. Here, refined Tuscan cuisine meets perfectly paired Antinori wines. Pure magic!

Day 4

Siena Secrets & Market Adventures This morning we're off to Siena, a UNESCO treasure that takes our breath away. Our guided walk through this medieval masterpiece leads us to the famous Piazza del Campo and the stunning Duomo di Siena. And if you're in the mood for shopping, you're in luck — Connie says this is her favorite spot to find hidden gems! Later, we dive into the bustling markets of Greve and Panzano, watching Mauro in his element as he works his magic at Dario's (the world-famous butcher of Chianti) — there's always a line, but trust me, it's worth the wait! He moves through the market stalls like a culinary detective, picking perfect tomatoes, chatting with farmers, sniffing out the freshest pecorino, and negotiating for the most delicate prosciutto. "Every ingredient has a personality," he tells us with a wink. "You must listen to what it wants to become." Back at the villa, Mauro hosts one of his legendary wine and food pairing sessions — casual, fun, and guaranteed to teach you something new about Italian wines.

Day 5

Grand Finale Our final day begins lazily with breakfast and coffee on the terrace, because by now, we've learned to embrace the Italian art of taking our time. The afternoon takes us through Castellina's historic center, where we explore the fascinating Underground Tunnel (Via delle Volte) before treating ourselves to a private tasting of aged Chianti Classico Riserva wines. For our farewell dinner, Mauro and Connie have planned something special. Under a canopy of stars, we feast on a meal where everything comes from within 10 kilometers: wild mushrooms gathered that morning, local lamb slow-roasted with herbs from the surrounding hills, and the perfect dessert — cantucci cookies dipped in Vin Santo, capturing the very essence of Chianti. Each course comes paired with the region's finest wines, of course. As the sun sets on our Chianti adventure, Mauro shares one last bit of wisdom: "Travel is not just about the food and wine. It's about connection — to the land, to history, to each other." And he's right. This week hasn't just been about incredible meals and amazing wines — it's been about learning to shop like an Italian, understanding centuries-old traditions, and most importantly, learning to relax, forget about time, and simply enjoy life.

Want to know the best part about traveling with Mauro? He doesn't just teach — he shares stories from the heart. Every tale, every tip, every tradition comes from his genuine love for this special corner of Italy. And somehow, by the end of the week, you're not just a visitor anymore — you're part of the story too.

Extra Treats Throughout Your Stay

• Private drivers whisk you between venues in comfort

• Exclusive access to wine cellars usually closed to the public

• Easy wine shipping so you can send your favorites home

• Flexible scheduling to catch seasonal festivals and events

• Optional sunrise hot air balloon ride over Chianti's stunning landscape