You may have the world if I may have Italy — Giuseppe Verdi

Upon arrival in Italy, your private driver will whisk you from Rome or Florence to a family-owned winery surrounded by rolling vineyards and silvery olive groves. Over the next two nights, you’ll settle into the rhythm of the Tuscan countryside, where every detail reflects a deep respect for land and season.

Your first evening is a celebration of your arrival. Gather for a special welcome dinner prepared with the freshest local ingredients — handmade pastas, garden herbs, and produce sourced just steps from the kitchen. Each course is thoughtfully paired with wines from the estate, chosen to highlight the balance and character of both the food and the land. As the sun dips behind the hills and glasses are raised, it’s the perfect beginning to your journey through Tuscany.

Today, you’ll join Marco Molesini, owner of Enoteca Molesini and renowned sommelier, for a private winery tour and tasting at the estate. Stroll through the vineyards, explore the cellars, and meet the winemaker to gain a deeper understanding of what makes this region so exceptional. It’s a day designed to bring you closer to the art and soul of Tuscan winemaking.

This evening, your driver will take you to a nearby hilltop town, where your group will have the evening free to dine as you wish. Wander its cobblestone streets, follow the aroma of wood-fired cooking, and let curiosity guide you to the perfect spot for dinner. It’s a night to Savor Tuscany at your own pace.

This morning, you’ll pack your bags and set out toward Cortona, your home for the next four nights. Along the way, we’ve arranged a special stop that captures the essence of Tuscany’s culinary heart with a private visit to Frantoio Pruneti, one of the region’s most celebrated olive oil producers.

Your experience begins with a guided tour of the mill and surrounding groves, where you’ll learn how the olives are cultivated, harvested, and pressed to create their award-winning oils. Afterwards, enjoy a hands-on cooking class that showcases the many ways olive oil enhances both food and drink, from traditional dishes to inventive cocktails.

By late afternoon, you’ll arrive in Cortona and settle into your beautiful apartment in the heart of town. To mark the beginning of your stay, stop by Enoteca Molesini for a welcome glass of wine, the perfect introduction to life in this charming hilltop town.

Today is dedicated to discovering the charm of Cortona, a town that feels like the heart of Tuscany itself. Begin your morning with a private wine tasting at Enoteca Molesini, where you’ll sample a curated selection of regional wines guided by expert insight and warm hospitality. From there, enjoy a leisurely lunch at La Dispensa del Preludio, a beloved local spot known for its fresh, seasonal dishes and relaxed atmosphere.

The afternoon is yours to explore at your own pace. Wander through the cobblestone streets, browse the boutiques and artisan shops, or simply find a quiet café to take in the view over the Val di Chiana.

As evening falls, return to your apartment and come hungry. Tonight, a private chef will prepare an unforgettable dinner in the comfort of your home away from home. Savor each course as it’s paired with local wines and flavors that reflect the spirit of Cortona—a true celebration of good company, good food, and the beauty of slow living in Tuscany.

Thursday is yours to design, a day to follow your curiosity and savor Tuscany in your own way. We’ll share a selection of optional add-ons, each one thoughtfully chosen from some of our favorite experiences in the region. Whether you’d like to visit another winery, unwind at a nearby spa resort, or spend the day in Siena taking in the grandeur of its historic streets and piazzas, we’ll help tailor the day to your interests. Or, if you prefer a slower pace, simply linger in Cortona and enjoy its inviting rhythm of cafés, shops, and quiet corners.

As evening arrives, you can choose between two distinct experiences. Join the town’s festive Wine, Dine, Shine celebration, where jewels, lights, and laughter fill the streets, or enjoy a more intimate evening at Al Tocco, where Chef Mattia Santiciolli will prepare a special multi-course menu created exclusively for your group.

On your final full day in Tuscany, we’ve arranged an experience that perfectly captures the spirit of the week. Based on your group’s preferences, we’ve hand selected another distinctive wine region to explore, this time accompanied by wine specialist Michela Santiccioli. Together, you’ll tour the vineyards, learn about the terroir and winemaking philosophy of the estate, and enjoy a private lunch paired with exceptional wines that showcase the character of the region.

After returning to Cortona, the evening is dedicated to celebrating the friendships and memories made along the way. Your farewell dinner will take place at Ristorante Ambrosia, where Chef Matteo Sciarri will prepare a thoughtful multi-course meal highlighting seasonal ingredients and local flavors. Surrounded by good company and great wine, it’s the perfect finale to your Tuscan journey — a night to savor every last moment before departure.

Today you say arrivederci to Tuscany, carrying with you the memories and connections that make this region so special. Over the past week, you’ve walked its ancient hills, met the people who devote their lives to its wines, and shared meals that reflect the soul of the land itself. 

As you continue your travels, we’re here to help guide the way. Our concierge travel services are available should you wish for recommendations on where to go next, from hidden hilltop towns to seaside villages, from the perfect trattoria to a stay that feels like home.

While your time in Tuscany may be complete, the journey doesn’t have to end. We invite you to join us on a future Savor & Cellar trip, perhaps through the sunlit vineyards of Sicily or the refined hills of Piedmont. Each region offers its own beauty, flavors, and friendships waiting to be discovered.

Buon viaggio, and until we meet again, cheers to the memories made in Tuscany.