Upon arrival in Italy, your private driver will escort you to Dievole, a picturesque working winery whose roots stretch back over a thousand years. Set among rolling vineyards and silvery olive groves, the estate offers a serene introduction to the Tuscan countryside. Over the next two nights, settle into its unhurried rhythm, where every detail reflects a quiet reverence for land, season, and tradition.

Your first evening offers a warm welcome to Tuscany. Gather for a special dinner at Novecento, prepared with the freshest local ingredients — handmade pastas, garden herbs, and produce sourced just steps from the kitchen. The courses are thoughtfully paired with wines from the estate, each one selected to highlight the balance and character of both the food and the land. As the sun sets behind the hills and glasses are raised, it’s the perfect start to your journey through Tuscany.

Today, you’ll be joined by Marco Molesini, renowned sommelier and owner of Enoteca Molesini, for a private tour and tasting at a nearby family-run winery. Stroll through the vineyards, explore the cellar, 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 tradition of Tuscan winemaking.

In the evening, your driver will bring you to a classic 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 depart for Cortona, your home for the remainder of the journey, with a compelling stop along the way that captures the essence of Tuscany’s culinary traditions. A private visit to Frantoio Pruneti offers an intimate introduction to one of the region’s most celebrated olive oil producers.

Your time at the mill includes a guided walk through the olive groves and production spaces, where you’ll learn how olives are cultivated, harvested, and transformed into award-winning oils. The experience, available only to Savor & Cellar guests, concludes with a cooking demonstration that explores the versatility of olive oil, showcasing its place in both classic dishes and more modern interpretations, including creative cocktails.

By late afternoon, arrive in Cortona and make yourself at home in the beautifully appointed and centrally located Apartment Vagnucci. By design, you’ll spend four nights in Cortona, creating space to settle in, form connections with locals, and experience the town beyond its highlights. Stop by Enoteca Molesini for a welcoming glass of wine, then take time to wander the streets before deciding where to enjoy dinner, with recommendations available should you wish.

Today is dedicated to discovering the charm of Cortona, a town that reflects the heart of Tuscany. Begin your morning with a private wine tasting at Marco’s wineshop, where you’ll sample a curated selection of wines from across Italy. Expert insight and genuine hospitality guide a tasting defined by your group’s curiosity and a seemingly endless selection of exceptional bottles. Afterwards, move from palate to plate with a leisurely lunch at La Dispensa del Preludio, a beloved local spot known for its fresh, seasonal dishes and relaxed atmosphere.

The afternoon is reserved for exploring in your own way. Browse the boutiques and artisan shops, visit the acclaimed MAEC Museum or simply find a quiet café to take in the view over the Val di Chiana. As evening falls, return to your accommodations and be sure to bring an appetite as we’ve organized a private chef to prepare an unforgettable dinner in the comfort of your private apartment. Savor each course as it’s paired with local wines and flavors that reflect the spirit of Cortona—a true celebration of good friends, good food, and the beauty of slow living in Tuscany.

Today’s plans are shaped around what appeals to you! We’ll share a selection of optional experiences drawn from some of our favorite places in the region. You might enjoy visiting a winery in nearby Montepulciano, unwinding at a spa resort, or spending the day in Siena exploring its ancient streets, historic cathedral and unrivaled Piazza del Campo.

As evening approaches, choose between two distinct dining experiences. The first, Wine, Dine, Shine, combines Italian wine, food, and jewelry at a family-owned restaurant in the heart of Cortona. Local gastronomy is elegantly paired with an array of wines from regions throughout Italy. And for those interested in the “jewelry tasting” part of the experience, you’ll be invited to sample and wear fine jewelry from DelBrenna for the evening! 

For those looking to enjoy a more quiet, intimate evening, we’ll organize dinner at Ambrosia, where Chef Matteo Sciarri will prepare a thoughtful meal highlighting seasonal ingredients and local flavors. Between courses, he’ll join you at the table to discuss the region’s evolving culinary scene, exploring how Cortona specifically is at the heart of many of these changes. Join in the conversation and embrace the opportunity to ask questions while learning from a local chef with deep knowledge on such an important part of Italian culture.

On your final day in Tuscany, we’ve arranged an experience that captures the spirit of the week with a visit to the acclaimed wine region of Montalcino. Accompanied by wine specialist Michela Santiciolli, you’ll explore estate vineyards, gain insight into the terroir and winemaking philosophy that shape Brunello di Montalcino, and sit down to a private lunch paired with an exceptional lineup of Brunellos that reflect the depth and distinction of the region. It’s not uncommon for the estate owner or winemaker to join the lunch, offering a personal glimpse into the people behind the wines.

After time in the vineyards, you’ll return with Michela to the wineshop, where there’s an opportunity to revisit and select some of the bottles you’ve enjoyed throughout the week. Any wines chosen can be shipped directly to your home, allowing you to enjoy a taste of Tuscany long after you’ve returned.

The evening is dedicated to celebrating friendship and recalling memories made during this time in Tuscany. Your farewell dinner will be hosted at Al Tocco, where Chef Mattia Santiciolli will prepare a delightful multi-course menu created exclusively for your group. The restaurant setting is uniquely beautiful and his food among some of the best in all of Tuscany. Surrounded by good company and great wine, it’s 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 heart and soul of the land. 

Whether you continue traveling through Italy or return home inspired, our team is here to assist with recommendations for additional adventures. 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. 

Until then, suluti to the memories made in Tuscany.