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Unlock Authentic Tuscany

Your Exclusive Chef-Led Wine Trip to Italy’s Heartland – October 2026

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Priority Waitlist Now Open — Only 8–14 Guests Per Journey

Marcus or Jamie Will Personally Share More Tour Details.

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Wake up in a 16th Century Medici Estate over looking Florence

Imagine awakening in a magnificent 16th-century Medici Estate, the golden Tuscan sun streaming through your window, revealing a breathtaking panorama of Florence and its iconic Duomo. This isn’t just a fleeting moment, but a cherished part of our most sought-after Italian journey. Your adventure begins in the historic embrace of Rome, gracefully winding through the enchanting regions of Lazio and Umbria, before culminating in the Renaissance heart of Tuscany. Along the way, we’ll explore sun-drenched vineyards and wander through the cobblestone streets of ancient medieval cities, each step a discovery, each vista a masterpiece.

 

This VIP Winery adventure is more than a tour; it’s an intimate exploration of Italy, personally guided by us, Marcus and Jamie Guiliano. We delight in sharing our treasured finds with you – from hidden gem restaurants where the flavors of authentic Italy come alive, to charming boutique hotels that feel like a home away from home, and, of course, the exceptional, family-run wineries where you’ll taste the passion in every glass. We believe in “non-touristy” experiences, taking you beyond the well-trodden paths to uncover the true soul of this captivating country.

Prepare to fall deeply in love with classic Italy as we reveal its authentic beauty and timeless allure. This journey is meticulously crafted to be a “soul-shifting” experience, rich with genuine connections and unforgettable moments. It’s no wonder this particular Italian dream consistently sells out quickly! Are you ready to discover why this is the Italian escape everyone is talking about?

A Taste of Tuscany: Daily Itinerary for a Gastronomic Adventure

  • Setting Forth from Rome: Our expedition starts from the Eternal
    City as we voyage towards the heart of Tuscany, where the wine heavens beckon.
  • Falesco Winery Rendezvous: Engage with the maestro, Riccardo Cotarella. Witness the artistry and dedication that mold the perfect
    vinous elixir.
  • Journey through Bagnaregio: Wander Italy’s mystic city, Civita di Bagnoregio. Unveil its architectural marvels, intertwined tales, and
    the hallowed San Bonaventura Cave.
  • Culinary Joy: Relish a Tuscan feast, with Bagnaregio’s vistas
    enhancing the flavors.
  • Alta Rocca Wine Resort Oasis: Nestle into opulent Italian comforts amidst verdant landscapes.
  • Vinous Indulgence: Explore Alta Rocca’s prized wines, a reflection of Tuscany’s terroir.
  • Dinner Delights: Experience Alta Rocca’s gastronomic excellence, a culinary journey through Tuscany’s heritage.
  • Orvieto Exploration: Traverse a city frozen in time; where every cobblestone whispers ancient tales, and Gothic cathedrals punctuate the skyline.
  • St. Patrick’s Well: Marvel at this medieval marvel, an ode to yesteryear’s architectural prowess.
  • Orvieto Flavors: A feast showcasing centuries of culinary artistry.
  • Mottura Wine Odyssey: Sip the region’s vinous gems, tales of sun, soil, and passion in each glass.
  • Evening Elegance: Mottura’s acclaimed restaurant promises an unforgettable Italian feast.
  • Montalcino Unveiled: Roam the sanctum of Brunello wines. Montalcino’s history beckons with its winemaking legends.
  • Corte Pavone’s German-Italian Romance: Embrace the fusion of German heritage with Italian vinous artistry at this organic wonderland.
  • Altesino’s Legacy: Journey into Brunello’s heart at Altesino. Treasures, from age-old vintages to the Vin Santo chamber, await.
  • La Magia’s Mountaintop Elixir: Revel in breathtaking vistas, complemented by wines that echo the passion of Tuscany.
  • Morning at Avignonesi: Traverse the estate, from its storied roots to Virginie Saverys’ passionate stewardship. Discover their commitment to nature, crafting wines that are as organic as the Tuscan air.
  • Siena Unfolded: Dive into a city where art, culture, and history meld seamlessly.
  • Gourmet Choices: Delight in Sienese flavors at Particulara or Campo Cedro, Michelin-star experiences assuring culinary rhapsody.
  • Night at Podere Spedalone: Retreat to this haven, where verdant expanses, farm-fresh dishes, and camaraderie blend seamlessly.
  • Torciano’s Truffle Odyssey: Embark on an exhilarating truffle chase at Torciano. Later, let wines and truffle delicacies serenade your senses.
  • Montenidoli’s Legacy: Traverse Elisabetta Fagiuoli’s world, where abandoned Tuscan vineyards bloomed again. Discover their unique terroir and Elisabetta’s community-driven dreams.
  • Winery Feast: Dine amidst vineyards, celebrating Tuscany’s myriad flavors.
  • Medieval Wonders: Revel in San Gimignano’s towering history, its 13th-century skyline, and UNESCO recognized splendor.
  • Villa Cafaggio’s Vinous Ensemble: Embrace wines crafted through time, reflecting Tuscany’s soul.
  • Night at San Vito: Rest amidst rustic comforts, where nature’s bounty and organic practices forge wines of distinction. Dine with wines that echo Tuscan whispers.
  • Malenchini Odyssey: Dive deep into wines that mirror Italy’s soul and history.
  • Florentine Wonders: Walk through renaissance magic, with artisans’ crafts beckoning.
  • Culinary Fantasia: Cucuulia’s culinary tapestry, curated by Chef Oliver Betancourt, promises a gustatory spectacle.
  • After a final Italian breakfast, we’ll arrange your transit to Bari airport, your hearts and minds filled with the unforgettable tastes and experiences of Southern Italy.
  • As our Italian wine saga concludes, we return to Rome, memories and Tuscan wines in tow, promising a reunion with the enchanting lands of Italy.