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

Woman enjoying a glass of wine and the view in Montalcino, Italy

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.

Countries Visited

Italy

Places Visited

Rome, Siena, San Gimignano, Greve in Chianti, Radda in Chianti, Montalcino, Pienza, Montepulciano, Torgiano, Montefalco, Bevagna, orvieto, Roma, Frascati, Genzano, Ariccia

Suggested Duration

9 Days

Customizable Itinerary

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Day 1

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:

Tour
Transfer
Accommodation
Dinner
Day 2

Siena – Indelible Hills of Tuscany

Day 3

Siena – True Tuscan Wheels

Day 4

Torgiano – Finding the Right Truffle

Day 5

Torgiano – Wine Discovery in Umbria

Day 6

Rome – On the Road to Rome

Day 7

Rome – The Lazio Country

Day 8

Rome – The Diverse Flavors of Rome

Day 9

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.

4.9

Verified Traveler Reviews

Based on 967 reviews

Italy Trip Review: Milan, Florence, Lake Como, Venice, 11 Nights

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.

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Italy Tour Review: Tuscany, Florence, Montalcino, Castellina, Chianti, Wine Tasting, Cheese Experience, Local Cuisine, Walking Tour, 9-Day Trip

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.

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Italy Trip Review: Florence, Montalcino, Chianti, Wine Tours, Art, Museums, Local Cuisine, Culture, 8-Day Tour

The trip Zicasso's travel consultant designed for us was absolutely perfect in every way! The hotel in Florence was a beautiful place to stay. The rooms were very clean and comfortable, and the breakfast was outstanding. I loved seeing art everywhere in the hotel and the staff were helpful and accommodating.

All of our drivers were friendly and helpful. As two women traveling in a country where we didn't speak the language, our drivers made us feel safe and well taken care of.

Our guide for the Uffizi, Accademia, Bargello, and the Duomo was incredible! She enriched our experience with her extensive knowledge base and delightful personality. We formed a fast friendship and were sad when our time with her came to an end. She was one of the highlights of our trip. I can't say enough wonderful things about her! 

The wine tours were fabulous! We learned so much about the Chianti region. Each tour was well done, but Montalcino was the stand-out experience. It was so elegant and wonderful. Needless to say, we brought home several bottles...

I can't thank the travel consultant enough. From start to finish, she was absolutely lovely to work with. She understood exactly what we wanted and curated a trip of a lifetime for us! I fell in love with the art, architecture, people, food, and wine of the region, and hope to return someday.

I must also acknowledge our US contact. He was incredibly helpful any time he was called on to assist. So cheerful and positive.

I have already recommended Zicasso to many of my friends. I will certainly look forward to my next trip curated by your company.

Thank you for an incredible experience!

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Italy Tour Review: Venice, Florence, Tuscany, Lake Como, Milan, Truffle Hunting, Wine Tasting, Cooking Class, Boat Ride, 2-Week Trip

Our trip to Venice, Florence, Tuscany, Lake Como, and Milan was exceptionally well planned and executed by Zicasso's tour operator.

The transportation from one location to another was efficient, even when challenged by the high tides in Venice. Overall, the hotels selected were very good. The one in Montalcino was exceptional. Every guide was knowledgeable and professional. We appreciated their willingness to be flexible. Our driver for the ride to Como and back to Milan was personable and exceptional as well.

We really enjoyed the truffle hunting experience, the first wine tasting in Montepulciano, where we met the entire charming family, the cooking class in Bellagio with a chef who treated us like family, and the boat rides on Lake Como and to the islands in the lagoon of Venice. All of the dinner reservations were spot-on and when there was a slight misunderstanding regarding our wine tasting in Bellagio, where the staff at the hotel in Bellagio had no idea what had been arranged by our agency, this was quickly resolved by our guide through texts and emails with the agency.

The only aspect of the trip that could have been improved was day eight, when our activities, travel time, and late dinner reservation resulted in a late-night drive back to the villa. The hotel in Milan was difficult to find at first due to its location not being visible from the street. Once we found it and settled in, it was in an excellent location for our sightseeing. The gifts of sparkling wine at two of our stops was thoughtful and appreciated.

We thank our agent and the staff at the agency for a wonderful trip and would not hesitate to recommend the firm to our friends and family.

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Italy Tour Review: Bologna, Parma, Modena, Balsamic Vinegar Factory, Wine Tasting, Cuisine, Cooking Class, 2 Weeks
"We set out to experience culture and food, and Zicasso’s travel agency did not disappoint."

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Italy Vacation Review: Taormina, Cefalu, Palermo, Ortigia Island, Catania, Mount Etna, Cooking Class, Winery Visit, 9 Nights

I was connected with the travel company through Zicasso. What an amazing trip! Many thanks to our travel designer of the travel company!!!

Our travel designer and her expert team planned a trip to Sicily for my husband and I, my siblings, and my sister-in-law. We were six and everything about the trip was executed beautifully and with great attention to every detail.

We chose to go to Taormina, Cefalù, Palermo, and Ortigia Island, flying direct in and out of Catania. Our travel designer arranged all transfers by private van for the six of us and we never had to worry where or when we were going anywhere. She was able to make changes on the spot and accommodate our every wish.

Planning the trip was so easy, as she was available to chat with me on the weekends to answer questions and clarify details. She even made dinner reservations in every city. I cannot say enough about her willingness to be available and the choices she helped us make. From the terrific winery near Mount Etna to a drive up Etna, guided tours (we had an incredibly fabulous art historian showing us the churches of Palermo), a day at leisure on the beaches of Cefalù, and an amazing cooking class in Palermo, where we learned about and visited the markets, and made pasta and cannoli, every experience was better than the one before it.

We definitely recommend, with five stars, the travel company. Have them plan your trip to Italy! This was my first time back to Europe since 2004 and it was stellar!

I surely will use this company when I plan new trips to Italy, and Zicasso as well!

When we were trying to decide where to go, we chatted with travel partners in several European destinations. Zicasso chooses the best of the best and our experiences with each of them was exceptional!

We will be back to Zicasso when we travel to other destinations!!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

28,000+ Verified Traveler Reviews