Italian Indulgence: A Food & Wine Tour of Tuscany, Umbria, & Lazio

What to expect on this itinerary
Rome will make your mouth water with the ineffable flavors of cuisine emboldened with history and tested with time. Sip the bittersweet flavor of an espresso in view of detailed baroque fountains. Sample the crumbly herbaceous Pecorino cheese directly from the makers' shelf. Wander along vast vineyards blanketing the hillsides leading to medieval walls. Your custom tailored tour immerses you in the culinary delights of Italy, letting you bask in the flavors of fresh pasta and a culture known for its cooking. Traverse the countryside of Tuscany, Umbria, and Lazio to find perfection in the kitchen.
Customizable Itinerary
Siena – Introduction to Medieval Tuscany
The Tuscan hills roll along the landscape punctuated with cypress trees. The historic walls of Siena have protected the city for centuries, surrounding the towers and marble façade of the cathedral. Your private transfer meets you at Rome’s Fiumicino Airport and escorts you north into the famous Tuscan countryside. The height of the city’s power began in the 12th century. By the 14th century, the lavish artwork and architecture rivaled the beauty of Florence. Red clay bricks crafted from the earth outside the city shaped the rosy hues of the palazzo in the main square of Piazza del Campo.
The Torre del Mangia rises to a height of nearly 335 feet above the brick square. Two brothers erected the tower in the mid 14th century, which provides an elaborate panorama of Siena’s red-tiled rooftops with the emerald hills of Tuscany in the background. The black and white stripes along the Cathedral’s Gothic marble façade add a unique flair to the piazza, standing out from the surrounding red buildings. The large rose window provides beaming light to fill the nave. The interior contains mosaic panels along the floor with 56 different depictions of Biblical history.
After exploring the splendor of the historic city center, your guide meets you at the hotel and escorts you to a charming vineyard in the countryside for your welcoming taste of Siena. Your tasting menu fills the table with traditional succulent dishes of Tuscany, from roast boar to pici noodles. You have a sensational view of the landscape outside the window as the dining room fills with the mouthwatering aromas of dinner. Each dish is balanced with a perfectly paired wine produced on the vineyard. When you taste the roast boar and sip your wine, the flavors marry, combining the savory taste of the meat with the mineral rich quality of the wine.
What's Included:
Siena – Indelible Hills of Tuscany
Siena – True Tuscan Wheels
Torgiano – Finding the Right Truffle
Torgiano – Wine Discovery in Umbria
Rome – On the Road to Rome
Rome – The Lazio Country
Rome – The Diverse Flavors of Rome
Rome – A Flavorful Farewell
Trip Highlights
- Sample the celebrated wines Montepulciano on a wine tasting tour of Tuscany
- Indulge in a fabulous excursion to hunt truffles before tasting the bold flavor shaved over a traditional pasta dish of Umbria
- Visit a Tuscan dairy to learn the methods of creating regional Pecorino cheese before sampling the artisan flavor
- Enjoy an olive oil tasting in a small village to discover the differences in Virgin versus Extra Virgin Olive Oil
- Relish the delicate balance of aromas and tastes during a sampling of the wines produced in the celebrated town of Montefalco
- Delight in a flavorful lunch in a traditional village of Lazio with a view of the hills overlooking Rome
- Witness the opulent artworks and staggering history of Rome embodied in the architecture and displayed in the museum galleries
- Relish the creamy texture and large variety of flavors during a gelato tour of Rome
Detailed Description
The best of Italy can be found inside the homes of Italians, when the table fills with regional dishes and the wine flows freely. Your 9-day culinary tour leads you through the true culture of Tuscany, Umbria, and Lazio, revealing the celebrated flavors shaped by tradition, passed down through generations, and treasured by visitors and locals alike. Your gastronomical excursion begins with your arrival at Fiumicino Airport in Rome. Your private transfer meets you at baggage claim and leads you north to Tuscany at the town of Siena.
Your guide leads you on a tour of the medieval city before embarking on an introductory wine tour of a local vineyard. The next day, you venture into the Tuscan countryside to visit the towns of San Gimignano, Greve in Chianti, and Radda in Chianti. Stroll along the cobblestone streets of the historic towns before sampling the wines of the districts, each producing stunning varietals based upon the soil and microclimates. Travel to the towns of Montalcino, Pienza, and Montepulciano to discover the unique blend of medieval and baroque architecture rising above the hillside.
Visit the vibrant market of Pienza before touring a local dairy for an in-depth lesson on the methods of making the delicious Pecorino cheese. Then, you venture south to the region of Umbria at the town of Torgiano. The serene medieval streets lead you along the historic walls overlooking the lush plains and hills. Follow your guide on a truffle hunt before relishing the bold flavors of a regional lunch. Enjoy an olive oil tasting to learn the difference between the creamy varieties of oils.
Next, you uncover the treasures of Umbria with a tour of Montefalco and Bevagna. The former produces the sensational wines in vineyards overtaking the hills beneath the medieval towers. The latter town highlights the blend of Roman antiquity with medieval life. You sample the flavors of Umbrian gnocchi in the captivating town of Orvieto en route to Rome. Once in the Eternal City, you have the day at your leisure to stroll along the ancient lanes revealing the intricate balance of sweet and savory gelato. The following day takes you into the towns outside of Rome collectively known as the Castelli Romani.
Relish the flavor of a succulent lunch cooked over an open fire. Meander through elaborate gardens and palaces containing divine terraces in Frascati, Genzano, and Ariccia. Then, your guide escorts you through the city in search of the artistic tastes of history, from the ancient architecture to the Vatican Museums. In the evening, you indulge in the traditional cuisine of Lazio in a celebrated restaurant known for its regional specialties. Your private transfer meets you in the hotel lobby on your final day and leads you to the Fiumicino Airport for your flight home.
Starting Price
$4,100 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
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 878 reviews
We had a fantastic trip, all thanks to our travel specialist. We spent a few days in Siena, touring different Tuscan towns like Montepulciano, Pienza, and San Gimignano, and then we spent a couple of nights in Florence. All of our drivers and guides were very thoughtful that we had my two-year-old nephew with us.
See more
We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.
The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.
The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.
One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.
Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.
While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!
Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.
Every experience felt personal, meaningful, and special.
This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!
See more
When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.
Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.
Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.
A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.
Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.
When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.
See more
Zicasso’s travel agent was accommodating and helpful for our trip to Tuscany. Since there were so many of us, people had different needs. She was able to accommodate our differences and work out plans the best she could. We enjoyed all of the selections that she gave us, especially the dinner in the Chianti vineyard. Everyone loved that. We definitely recommend this travel company!
See more
This was our first time visiting Italy, and we were very excited to experience the country through a thoughtfully planned luxury itinerary. Overall, we had some wonderful experiences, but there were also several disappointments that affected our trip and that we feel are important to share.
Highlights
Venice was a highlight of our trip. We loved the atmosphere, scenery, and overall experience of being there.
The wine tasting experience in Tuscany was another major highlight. Our trip to Chianti from Florence was beautiful, and the Tuscan countryside was exactly the type of experience we had hoped for. Our cooking class with our instructor in Florence was also exceptional. Making fresh pasta and tiramisu while enjoying wine, music, and great conversation made it feel authentic and personal. These are experiences we will truly remember.
Areas That Fell Short
We would have appreciated much more advance guidance about how incredibly hot and crowded Italy would be during peak season in September. We experienced a significant heat wave and extremely limited air conditioning throughout the trip, including in hotels and fine dining restaurants. This made traveling much less comfortable than anticipated, particularly as first-time visitors to Italy.
We also visited four cities in just eight days, which in hindsight felt far too rushed. As first-time visitors, we were relying on the agency’s expertise to help us create a realistic itinerary. We would have appreciated being advised that this pace was too ambitious and that fewer destinations with more time in each would have made for a more relaxing experience.
We also did not particularly enjoy Milan and felt there was not much there that appealed to us. In hindsight, we would have preferred to spend more of our limited vacation time in destinations that were a better fit for us.
The Lake Como boat tour was canceled at the last minute because we were given the wrong pickup location. This was especially disappointing because it was an experience we had been looking forward to and had planned our day around. Having it canceled at the last minute due to incorrect pickup information was frustrating and felt avoidable. For a luxury travel itinerary, we expected a higher level of coordination and attention to detail.
Transportation was another area that fell short. The three-hour private drive from Venice to Milan was exhausting, particularly because the driver was blasting music throughout the journey. We also had a four-hour drive from Lake Como to Florence in cramped transportation with limited air conditioning, which was extremely uncomfortable given the heat. For a luxury itinerary, we expected transportation to be spacious, comfortable, and properly climate-controlled, especially for longer transfers.
The hotel in Florence was particularly disappointing. We found the atmosphere to be creepy and uncomfortable and did not feel that the property matched our preference for modern, understated luxury. The shower would not drain properly, and although maintenance told us they had fixed it, the problem continued. The hotel did have an excellent location, a balcony, and warm, attentive staff, which we appreciated, but the overall property was not a good fit for us.
Communication
One area where the agency excelled was communication. The team was consistently prompt and responsive through WhatsApp, which truly became our lifeline throughout the trip. Whenever we had questions or needed assistance, we were able to reach someone quickly, and we very much appreciated that level of accessibility and support while traveling.
Overall
Italy was beautiful, and we are grateful for the opportunity to experience it. However, the trip did not consistently feel like the luxury experience we had envisioned. For future clients, we would strongly recommend providing more candid guidance around itinerary pacing, September peak-season crowds, heat, limited air conditioning, hotel style, and destination selection, as well as ensuring greater attention to detail with transportation and excursions.
See more
We loved everything about our trip to Tuscany. We had great, comfortable hotels as bases to explore the beautiful countryside and towns. Our hotels had kind, welcoming staff. Zicasso's travel company provided helpful suggestions and reserved non-touristy restaurants and enjoyable, interesting activities: eating in Florence, wine tasting in Montalcino, and cheese making in Pienza.
See more





