A Foodie's Slow Tour of Tuscany

Tuscan pecorino cheese on display in Tuscany, Italy

What to expect on this itinerary

Cuisine runs deep in Italy, connecting families and reflecting the soul of the chef, whether cooking rustic pasta at home or preparing gourmet dishes in a restaurant. The scent of celebrated confections emanates from display windows along the main avenues. Luscious cheeses maintain complex flavors, offering insight into the care taken during their production. Ruby-tinted wines glow against the verdant hills and cypress trees. Your 8-day foodie tour of Tuscany takes you deep into local tradition by highlighting cuisines and methods of creation, from the farm and vineyard to the table, showcasing the labors of love with every sumptuous bite you take.

Countries Visited

Italy

Places Visited

Rome, Montepulciano, Pienza, Castellina in Chianti, Greve in Chianti, Florence, Siena, San Gimignano, Montalcino

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Developing Italian Sensibilities

Italy is known as much for its delicious cuisine as its inspiring architecture spanning millennia. When you arrive in Rome, you find more than just the Colosseum standing proud, watching over the whitewashed stones of the Roman Forum. St. Peter’s Basilica rises above the city, adding to the elegant skyline of the surrounding cupolas of the city. The aroma of freshly made pasta fades with the sweet and enticing scents of creamy gelato emanating from the countless gelaterias. Your private transfer meets you at Fiumicino Airport and escorts you to a luxurious hotel situated in the heart of the historic city center. The allure of Italy radiates around you, from the gentle splashing of the Trevi Fountain to the blossoming gardens of Villa Medici.

A true introduction to the city is saved for dinner when you enter a restaurant producing authentic dishes of Rome with innovative twists near the vast public square of Campo De’ Fiori.  The menu changes with the seasons, utilizing ingredients from local farms. The outdoor patio looks out onto Piazza della Cancelleria. Locals stroll past without a care in the world, intoxicated for a moment by the aromas drifting from the restaurant doors. When the cacio e pepe hits the table, pasta in a cheese and pepper pan sauce, you find how stunning and complex a simple dish can taste.

What's Included:

Transfer
Accommodation
Dinner
Day 2

Introduction to Tuscan Tastes

Day 3

Road to Chianti

Day 4

Renaissance of Flavor in Florence

Day 5

Florence Gourmet

Day 6

Journey to the Middle Ages

Day 7

Winning Wines of Tuscany

Day 8

Sensory Memories

Trip Highlights

  • Savor the texture and complex flavors of the King of Wines with a sampling of Brunello in a traditional enoteca (wine repository) in Montalcino
  • Indulge in the crumbly texture and rich tastes of goat cheese on a family-run Tuscan dairy farm
  • Learn how to make unique and captivating gelato from a celebrated gelateria (Italian ice cream shop) in Florence
  • Enjoy a private tasting of Pecorino cheese after viewing the cheese-making process
  • Witness the ancient techniques of drying and harvesting herbs around the Chianti region
  • Taste the difference of olive oil productions with a sampling at a family-run organic olive oil farmhouse
  • Discover the unforgettable ambiance of Renaissance and medieval towns around the Tuscan region, adding to the indelible atmosphere 

Detailed Description

The pleasures of food bring community and family together. Your custom-tailored tour of Tuscany takes you into the slow food movement, allowing you to bask in the flavors of food and wine, savor the culture and heritage, and delight in the majestic surroundings. Your food discovery begins with your arrival in Rome. Your private transfer meets you at the airport and escorts you into the Eternal City. Your first dinner in Rome provides a perfect introduction to Italian cuisine and the slow food ideals, where you don’t just have dinner but experience it.

The following day, your guide takes you into Tuscany, where the celebrated hills of the province roll along the horizon. In the city of Montepulciano, you embrace the medieval town and sample the wines of the region at a historic enoteca located inside a former historic city jail. Following lunch, you delight in a tour of a farm famous for its Pecorino cheese near the Renaissance city of Pienza. Along the hills of Chianti, you stop at Castellina in Chianti for insight into the herbs of the area and the ancient techniques employed to harvest and dry.

Continue to the historic town center of Greve in Chianti and a nearby goat farm that produces fresh and zesty goat cheeses. In the remarkable city of Florence, your guide leads you on a tour along the cobbled streets, from the church of Santa Croce to the marble Duomo. In a flavorful gelateria, your guide leads you through the process of making gelato, tasting the unique and fabulous flavors along the way. The next day, you continue your exploration of Florence, taking the time to explore the museums and elegance of the city, with dinner at a restaurant providing a combination of decadence and tradition.

Outside of Florence, your tour guides you through the medieval towns of Siena and San Gimignano. Discover the history of Siena’s famous horse races and the sensational towers of San Gimignano, sampling exquisite olive oils at a family-owned farm along the way. Once in Montalcino, the vines, which produce the King of Wines, Brunello, decorate the countryside outside of town. Visit a local enoteca inside the historic fortress and tour cellars lining the medieval streets. On your final morning in Italy, your private transfer escorts you to the train station in Rome where you continue onward to Fiumicino Airport for your flight home.

Starting Price

$3,600 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 1050 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 Trip Review: Rome, Siena, Orvieto, Venice, Pienza, Vatican, Colosseum, Roman Forum, Vespa Tour, E-Bike Tour, 10 Nights

Our trip to Italy was amazing! The tours that were organized for us were all excellent and engaging. 

The Vespa sidecar tour was an incredible way to kickstart the trip and our two teenage boys really enjoyed it. Our walking tours of the Vatican museums and the Colosseum and Roman Forum tours with our guide were excellent. We loved her. She was fantastic. Our tour of the crypts and catacombs was very interesting and the guide was very good.

The hotels were very nice and accommodating, especially in Rome and Venice. The car rental in Rome was good and the car was the perfect size for what we needed. It was just big enough to fit our luggage. 

The hotel in Orvieto was a bit spartan and had plumbing issues. Our tour guide in Orvieto was also great. The hotel in Siena was very nice. Our tour guide in Siena was very nice, but we had some difficulty hearing her. She did explain things nicely and took us to some interesting locations around the city, but not being able to hear her was a little challenging. The e-bike tour in Montepulciano was incredible. The scenic landscapes and the visit to Pienza was a nice surprise. 

Returning the car in Florence was very difficult and our only suggestion is that on the travel documents, the return address be included on the page of the event. We did not think to look back at the rental agreement. Driving in Florence is very difficult and can be overwhelming for some people. 

The train station was organized and it was easy to locate the train. The train ride itself was very easy and fast. 

Venice was outstanding. Our hotel was beautiful and comfortable, and the breakfast was incredible. Due to the difficulty we had in returning the car in Florence, our travel company was kind enough to buy us dinner at an wonderful restaurant in Venice, which was one of the highlights of the trip. 

Our family had a wonderful experience and the trip was so well planned and organized. I will be using our travel company for future trips and, on behalf of my family, I would like to thank you for the time of our lives!

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Italy Family Vacation Review: Venice, Verona, Florence, Tuscany, Siena, Rome, Biking, Cooking, Wine Tasting, Olive Oil Experience, 10 Nights

Zicasso's travel company planned the most amazing trip to Venice, Verona, Florence, Tuscany, Siena, and Rome for our family of five. It was the best trip I've ever taken, and having all the details covered by them and plans and tickets sent to us via WhatsApp allowed us to really live in the moment and not have to think about what was next. I loved every second. I cannot wait to plan another trip to Italy to experience the southern half of the country.

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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