Quintessential 10-Day Tuscany Food and Wine Tour

What to expect on this itinerary
During this 10-day Tuscany wine and food tour, indulge in the grandeur of rustic cuisine and develop an intimate understanding of the gorgeous landscape. Your private tours led by specialist guides offer insight into the heritage of local flavors. This customizable tour will shine a brighter light on Tuscany’s culinary marvels, such as visiting renowned winemaking regions, basking in the enticing aromas of a private kitchen, and scouring woodlands for the elusive white truffle.
Customizable Itinerary
Florence – Introductory Dinner
Florence is a fascinating city of art, fashion, tradition, and gastronomy. Here, elegant palaces line cobbled lanes, and the aroma of freshly brewed espresso lingers among the scattered bakeries. Your flight will land at Florence Peretola Airport, where your private transfer will greet you upon your arrival and escort you into the heart of the city. After settling in to the comforts of your luxurious accommodation, your guide will introduce you to the marvels of Florence. First, you will explore the bustling neighborhood of San Lorenzo. Eventually, you will step into the majestic display of architecture in the San Lorenzo Church.
What's Included:
Florence – Private Cooking Class
Florence – Gelato Tour of Florence
Chianti – Chianti Wine Excursion
Chianti – Winemaking in Chianti
Chianti – Sample Cheeses and Wines
Siena – Walking Tour and Enoteca Visit
Siena – Bolgheri Wine Tour
Siena – Private Truffle Hunt
Siena – Departure
Trip Highlights
- Craft your own wine in the cellar of a private vineyard under the guidance of a working oenologist
- Learn how to master the art of handmade pasta during a private cooking class with a celebrated Florentine chef
- Delight in the flavors of Chianti Classico when visiting a celebrated winery near the antique walls of Radda in Chianti
- Enjoy a private demonstration and workshop on the process of making pecorino cheese on a farm outside of Pienza
- Bask in the charming ambiance of Bolgheri’s small streets and quiet artisan shops before visiting a celebrated vineyard to taste super Tuscans
- Indulge in the robust and earthy characteristics of truffles during a lunch that focuses on the exceptional ingredient after a private truffle hunt
- Witness Michelangelo’s marvelous sculptures, such as his imaginative and intricate depiction of the biblical warrior David, in the Galleria dell’Accademia
- Embrace the diverse flavors of gelato in Florence during a private gelato tour
Detailed Description
Your 10-day food and wine tour of Tuscany will feature the luxurious landscape that is celebrated for its sprawling vineyards and country roads that are lined with cypress trees. Your specialist guides and private transfers will provide an immersive experience, during which you will delight in Italy’s authentic culture, continued traditions, and remarkable flavors. You will also discover how the gastronomy of Tuscany derives from centuries of gastronomic customs. Furthermore, you will gain insight into the history of the region and its connection to greater Italy while indulging in the unspoiled scenery and welcoming ambiance of medieval towns.
Your food and wine tour of Tuscany will begin with your arrival at Florence’s international airport, where you will meet your private transfer. You will have three nights in Florence, starting with an introductory dinner that will highlight the delicious flavors of Tuscan cuisine. A historically based tour of the city will present the layers of medieval and Renaissance history through the lens of art at the Uffizi Gallery. Afterward, you will partake in a private cooking class that will teach you how to perfect traditional handmade pasta. You will then continue to uncover the marvels of Florence with a visit to the Galleria dell’Accademia to view Michelangelo’s David before partaking in a fantastic gelato tour. This tour will provide you with a glimpse of the unique history and best artisanal flavors of the city.
Your three nights in Chianti will begin with visiting the medieval towns that produce the wines of the region, beginning with Radda in Chianti. You can sample a variety of wines in a historic wine bar known as an enoteca. You will have a special day at a local vineyard in Chianti, where you can produce your own bottle of wine under the guidance of a trained oenologist. In the town of Pienza, you can enjoy the Renaissance architecture and serene ambiance before learning about the local connection to pecorino cheese. Afterward, you will participate in a cheese demonstration, workshop, and sampling on a local farm.
You will then transfer to Siena for three nights. Here, you will discover the preserved medieval wonder of the city with a private walking tour of the historic streets and structures. You will also visit a historic enoteca for a sampling of the local wines. You will also have a half-day visit to the town of Bolgheri, which is a town that possesses the feeling of being discovered and surrounded by natural beauty. You will visit a nearby vineyard for a tasting of the specialty wines that are produced in the region, such as the famous Super Tuscans. Your final tour in Tuscany will take place in the woodlands outside of Siena. Here, you will search for truffles with a seasoned guide, which will result in a marvelous lunch that focuses on the robust flavors of truffles.
Starting Price
$4,500 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.
Verified Traveler Reviews
Based on 3720 reviews
I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.
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The trip was absolutely beautiful and well planned. Zicasso's travel expert did a fantastic job and she was on top of everything. She texted me every night with the next day's plans. The only negative aspect of the trip was that the Sorrento hotel had no air conditioning. The rooms and lobby were extremely hot, hovering around 80° day and night.
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My husband and I had utilized the services of Zicasso for prior journeys to Italy, Southeast Asia, and Australia/New Zealand. For our recent trip to Matera and Puglia, I requested an agency located in Italy that specializes in travel to Italy. We selected a company that was on a magazine’s A-list of travel advisors.
Our travel consultant listened to and respected my requests for certain activities (private food, historical and boat tours, wine tastings, cheese making) and types of accommodations (properties that offered a shaded area to relax and read). She also emailed answers to my numerous detail-oriented questions (the curse of having personally worked as a tour guide). She sent a lovely gift to our first hotel and called halfway through our vacation to check in with us. Communication via text with WhatsApp was convenient and used frequently. Most importantly, when we had a problem with one of our accommodations, she followed up (even after our trip had ended) and graciously offered some compensation.
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Italy’s beauty is legendary—its rolling landscapes, vibrant culture, incredible cuisine, and deep history are truly one of a kind. But what made our trip truly extraordinary was the care, creativity, and attention to detail that the Zicasso travel company team brought to every part of our journey.
Our 12-day family adventure—with three teenagers!—was the perfect balance of guided exploration, fun hands-on experiences, and thoughtfully chosen hidden gems. Every stop offered something special for each of us, which is no small feat when traveling with a group of different interests.
While we’re fairly seasoned travelers, having the added support of your concierge service via WhatsApp was a game-changer. Any small questions or needs were handled quickly, warmly, and with a level of professionalism that gave us total peace of mind.
And the hotels—just wow. Every property was not only comfortable and welcoming, but also perfectly located, making it easy for us to explore and enjoy each destination to the fullest.
A heartfelt thank you to the entire travel company team for creating such a seamless and memorable experience. We can’t wait to plan our next adventure with you.
Grazie mille and arrivederci for now!
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Zicasso's travel experts made this trip effortless for us! They were responsive to my many questions and created a memorable trip for my daughter and me that included all of our favorite things, addressed any concerns I had, and stayed within our budget. Every detail was planned and communicated flawlessly. My daughter and I only had to pack our bags and enjoy every minute of this trip of a lifetime. I highly recommend Zicasso and their travel company!
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We just got back from an amazing two-week vacation with our children and our eight-year-old granddaughter. The travel specialists at Zicasso's tour company were incredibly knowledgeable, responsive, and professional. They took all of my ideas and managed to incorporate them seamlessly into our itinerary. I had quite a few requests and even made some last-minute changes, which they accommodated without any hesitation. One specialist, in particular, was exceptionally kind and helpful!
The organization of the trip was smooth and effortless. The transportation, drivers, and guides were all top-notch! We traveled in clean and well-maintained Mercedes vans, with well-dressed and personable drivers. The local guides were not only knowledgeable, but also spoke English clearly, sharing fascinating insights that allowed us to dive deeper into the history and culture. The hotels we stayed at ranged from good to very good. If I were to plan this again, I might choose a different location in Rome; the area was a bit congested and the hotel could use some upgrades, but it was conveniently situated.
The wine tastings were enjoyable and dinner at the vineyard was truly magical! Our standout activities were the cooking classes in Florence and Rome. The chefs were professional and imparted a lot of knowledge, giving us valuable skills to take home.
The highlight of our trip was definitely the private boat charter in Capri! We had a perfect day on a brand-new yacht, with an experienced captain and crew who took us to hidden caves away from the crowds, allowing us to swim in stunning locations. It was an absolutely fantastic trip!
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