Wine & Dine in Italy

Main Destination Italy

Wine & Dine in Italy

Tuscany & Umbria

Embark on an unparalleled journey through the heart of Italy's most renowned wine regions—Tuscany and Umbria—where luxury, gastronomy, and heritage converge. This exclusive itinerary invites you to immerse yourself in Italy's rich winemaking traditions and savor its culinary treasures, all while staying in some of the country’s most prestigious accommodations.

Your adventure begins in Florence, where you’ll be greeted with personalized service and enjoy a welcome dinner at a top-rated restaurant. From Florence, you’ll traverse the stunning Tuscan countryside, exploring the legacy of the Antinori family at their architectural marvel of a winery and dining at the Michelin-starred Osteria di Passignano.

The journey continues with a truffle hunt in the rolling hills of Tuscany, offering a unique opportunity to discover the art of truffle hunting with experts and savoring the delicacies in an exclusive lunch. This is followed by indulgent stays at luxurious countryside resorts, including Castello del Nero and L'Andana Tenuta, where you’ll experience both relaxation and refined dining.

In the Bolgheri region, you’ll tour the prestigious Ornellaia winery and enjoy a gourmet lunch crafted by their talented chefs. Your exploration of Tuscany's wine country includes visits to iconic wineries such as Petra and Le Ripi, where you’ll sample exceptional wines and delve into the innovative techniques that define the region’s winemaking.

The itinerary also includes a focus on local specialties, with visits to renowned cheese farms and charming towns like Massa Marittima and Montepulciano. Here, you’ll taste artisanal Pecorino cheese and explore the medieval and Renaissance heritage of these picturesque locations.
Transitioning to Umbria, the experience continues with a visit to the Torgiano Wine Museum, where you’ll explore 5,000 years of wine history. In Assisi, you'll discover the city's spiritual and historical significance, including a tour of the Basilica di San Francesco.

On the way to Rome, visit Orvieto, its stunning Duomo with Luca Signorelli's magnificent frescoes. Conclude the journey with an exclusive, after-hours visit to the Vatican Museums. Explore treasures like the Sistine Chapel and Raphael’s Rooms without the crowds.

Throughout the trip, you'll enjoy luxurious accommodations, from Florence’s Four Seasons to the exclusive Castello di Velona, and savor exquisite meals and wines paired with stunning regional flavors. Each day combines rich historical exploration with exceptional culinary experiences, promising a journey that celebrates Italy’s finest wine and gastronomy.

Terms, conditions and restrictions apply; pricing, availability, and other details subject to change and/ or apply to US or Canadian residents. Please confirm details and booking information with your travel advisor.

What our guests thought of this experience:

We did not really know what to expect. The food, the wine, the truffle hunting, the cooking class were all terrific. Not too much time spent on the bus. The private tour of the Vatican was so inspiring and wonderful. It would be very hard to replicate this trip as an individual. This is a unique experience to meet some great new people, taste some delicious wine and to learn more about them. This is a trip anyone who has not been to Italy can enjoy as can people like us who have already visited Italy numerous times.

Chris V.

Joy did an exceptional job designing and executing our trip. Her comprehensive attention to detail provided everything from knowledgeable local guides, special wine and dining experiences, to making our hotel check-in experiences seamless and easy. I think that she did an exceptional job choosing the personnel, the special experiences, the hotels, the driver, the guides....which resulted in an experience that we would not have been able to achieve without her savvy skill. The Sommelier Mladen is a rock star! His smile, laughter and warm personality added to our enjoyment of the trip. His knowledge and wine selection at our evening meals were definitely value added to our experience. It was a very special experience. Again, many aspects would not have been possible without Joy's planning and execution. We made many wonderful memories and will treasure those moments of awe, delight and laughter forever.

Marie F.

This trip was well planned and seamlessly executed. It provided fabulous Italian experiences including not just truly amazing food and wine, but exploring hilltop villages, truffle farm, organic farm, and cheese making, all at the same time while making new friends from our club! Traveling together is just more fun! Also, there were many simple pleasures difficult to put value on -  like not having to schlep luggage from place to place, but transported for us to the next hotel and placed in our room by the time we arrived! Job well done both Mladen and Joy!

Lisa G.

If you are looking for a 5-star trip that exceeds your expectations and if you have a great Sommelier like, Mladen Stoev, as your guide we would highly recommend this trip! The careful planning and attention to our needs and comfort made our experience an exceptional one. A trip that was as perfect as one could hope for!

Susan B.

This trip was so amazing for us. I was nervous not being involved in the trip plan like I normally would be. I have to say it was better than any trips I have planned. To us this was a perfect delivery of an amazing wine, food and history experience in one of the most beautiful places in the world. Scenery that takes your breath away; experiences that you are not likely to find yourself; with a relaxed, seamless execution; and a love for the experience that is contagious. A sommelier added tremendous value to our trip. Mladen made the experience fantastic - growing a deep appreciation not only for wine but the soulful nature of experiencing wine and making new friends. His deep understanding of wine and his enthusiasm for it was one of the many highlights of our trip. He helped grow our appreciation at a much deeper level.

David M.

I felt like I was in a dream of pure magic. Every need was well taken care of above my expectations. Mladen was what made the trip so special. His high energy, sense of humor, knowledge of fine wine, food and life is what I love the most about the trip.

Pia M.

The design and management of this Italian experience were very well planned and professionally run. There is no better and stress-free way to experience Italian culture, art, architecture, culinary styles, and regional wines.

Alison V.

I would recommend highly and not hesitate to travel with Mladen & Joy again and this wonderful group who I can now call my friends. We laughed always, drank and ate fine foods every day and experienced beautiful parts of Italy. Love the truffle hunt, the cooking class, the dinner with Salvatore Ferragamo. The Sistine Chapel was an unbelievable experience. Many thanks for the trip of a lifetime!!!! It was positively the most wonderful travel experience I have ever had. Every detail was taken care of with worry free travel for all. Made friends for life!

Louise P.

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