Historical Immersion Tour of Stunning Tuscany

What to expect on this itinerary
Your customizable 10-day historical tour of Tuscany will lead you from Florence to Siena and from Chianti to the Val d’Orcia. This tour immerses you in celebrated artworks, notable grape varietals, antique defensive walls, and dramatic cathedral facades. Discover the authentic beauty of the countryside among rows of cypress trees and uncover the secrets of crafting handmade pasta.
Customizable Itinerary
Florence – Fabulous Introductory Tour
Florence is a majestic city that is steeped in history. Your private transfer will greet you at Florence Peretola Airport upon your arrival in Tuscany and escort you to the comforts of your gorgeous hotel in the heart of the city. After settling into your accommodation, you will meet your guide in the lobby and set out on an introductory tour of Florence’s captivating history. This tour will lead you from the famous Ponte Vecchio to the renowned Duomo. The unreinforced brick dome stands at 376 feet tall.
What's Included:
Florence – Renaissance History and Art
Chianti – Wine Tour of Chianti
Chianti – The History of Siena
Val d’Orcia – Private Cooking Class
Val d’Orcia – The Hilltop Villages of Val d’Orcia
Lucca – Artisan Charm and Beauty at Volterra
Lucca – The Architecture of Lucca
Lucca – Venture to Pisa and Livorno
Lucca – Departure
Trip Highlights
- Embrace the sensational detail and impressive design of Michelangelo’s David when visiting the Galleria dell’Accademia
- Witness the exceptional collection of artwork that is featured at the Uffizi Gallery, such as Titian’s Venus of Urbino
- Wander among the dramatic architectural design of the Cattedrale di Pisa, which blends Pisan Romanesque and Gothic designs
- Discover the history of Tuscan cuisine and the importance of continued culinary heritage during a cooking class with a master chef
- Delight in the traditions of wines that have been crafted in the Chianti and Val d’Orcia regions
- Find marvelous Etruscan remains and paintings from the 1st century BC inside the Town Museum of Montepulciano
- Learn the preserved art of Alabaster carving during a private demonstration and workshop in the medieval town of Volterra
- Enjoy an exclusive tour of the Bargello Museum to view the marvelous galleries that host work from master artists, including Donatello
Detailed Description
You will embrace remarkable heritage and culture during this 10-day historical Tuscany tour. With private transfers, luxurious accommodations, and specialist guides, this tour will immerse you in the elaborate past of one of Italy’s most iconic regions. You will have the ultimate experience of exploring secluded villages, charming landscapes, and opulent cityscapes. You will also experience the overlooked canals of Livorno, the celebrated wines of Montepulciano, the renowned list of Pisa’s Leaning Tower, and the ways in which the masters of Renaissance art in Florence continue to reflect the history of the city and greater Italy.
Your historical tour of Tuscany will begin with your arrival at Florence’s international airport, where your private transfer will meet you at baggage claim. You will have two nights in Florence, and your knowledgeable guide will provide an introductory tour of the majestic city that is known for its art, architecture, and culture. You will traverse the famous Uffizi and Accademia museums to view the work of master artists, such as Botticelli and Michelangelo. Two nights in the Chianti region will highlight the splendors of the Tuscan countryside, beginning by unveiling the specific flavors of Chianti wine that has made it popular over the centuries.
You will continue to the Val d’Orcia for two nights. You will learn the art of crafting handmade pasta under the guidance of a chef who is experienced in the traditions of Tuscany’s Cucina Povera. Outside of Pienza, you will visit a local farm to learn the steps to making the special cheese of the preserved town before partaking in an artisan workshop that will teach you about the preservation of local traditions.
Three nights in Lucca will begin with an artisan demonstration of carving alabaster before a guided tour has you traversing the ancient city of Volterra. A full-day tour of Lucca will take you along the famous walls and through the winding cobblestone lanes that surround the Torre Guinigi. Venturing to Pisa will highlight the beauty of Gothic and Romanesque designs in the former naval powerhouse, and your time exploring Livorno will shine a light on the grandeur of the seaside city.
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
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 1015 reviews
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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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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Zicasso’s trip planner with the travel company were very helpful in planning our trip as to where and what we wanted to do and see. We were able to explore Como, Tuscany, the Chianti region, and the Amalfi Coast. The hotels were exceptional and we were well taken care of at each place, offering their own specialties. I would definitely recommend our trip planner to anyone looking to plan a trip to Italy.
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Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.
Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.
Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.
Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.
Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.
We travel a bunch and I would highly recommend using Zicasso's travel partner.
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Kudos to Zicasso’s tour operator! This is our second time using them, and they didn’t disappoint us. They had to deal with two families, seven in all, all adults, with two separate trips. One trip for all seven to Rome and Florence. Two for Naples and Ischia.
The apartment in Rome was in a good location for us, as we usually stay near there. The only problem I found in this apartment was the smaller unit had a step down into the living room. The floors are dark, and the step needs to be highlighted so one remembers to step down. Several of us kept missing it, and luckily no one fell. Other than that, it was a nice apartment.
In Florence, our apartment was perfect. My husband and I would stay there again; however, it has four bedrooms, four baths, a nice kitchen, and a large living room, so it would be a little big for two people. It was perfect for families. It is on the third floor.
Since my husband and I have been to Rome and Florence many times, we did not have too many requests for tours. My cousin and her family were first-time visitors. I suggested a tour of the Vatican Museums, Ancient Rome, the Accademia Gallery, the Duomo Skywalk, a private tour of the Uffizi Gallery, the Vasari Corridor, and the Boboli Gardens. In Rome, all seven of us did a golf cart ride at night, which seemed to be a big hit. We also had a wine tasting and olive oil sampling in Chianti, which was very nice.
At one point, we thought we were going to have a wedding proposal. A place was planned for the proposal at one of the wineries. Unfortunately, the groom-to-be decided not to do it there since the future bride’s parents would not be there. I felt bad with all the work the travel company did to make this day special for the couple.
Since we were two families, all adults, sharing vacation rentals, the tour operator found two apartments to meet our needs. All of our drivers and guides were on time and very knowledgeable.
We made some last-minute changes on our trip from Florence to Ischia. Changes to the train tickets were made, but we were asked to check with the ferry service to see if they could take us earlier. Our driver went with us to the ticket office and was able to exchange our ferry tickets. Then we notified our travel agent, so they could call the hotel to send our driver earlier than planned.
We have used this tour operator before and would highly recommend them. The hotels they selected were excellent. We stayed at our hotel in Naples last year and asked for the same hotel again. The views were fantastic from our room, and the rooftop bar had views of Mount Vesuvius and the Bay of Naples. The staff were superb, and there was a wonderful breakfast.
We also asked for the same hotel in Ischia, but that hotel closed earlier this year. Another property was selected, our resort in Ischia. Unfortunately, we did not get a chance to use the spa this time, but the hotel had beautiful views from the restaurant, terrace, and our room. Both hotels were beautiful, and the staff were very attentive. Our resort in Ischia was not far from Ischia Porto. A bus stop was a short walk away, and the return stop was right in front of the hotel. The food and drinks were great, and we even walked into town one night, which took about 15 minutes.
I can’t wait to use the travel company again next year.
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Zicasso's travel designer and the tour company did a super job of helping organize a trip that not only met our wants, but also required some changes due to a couple of rain days and a logistical challenge. They were super-proactive, responsive, and communicative. Also, all of the hotels, guided tours, and private drivers were excellent!
We visited Florence, Chianti, and Sorrento/Amalfi Coast, and each leg was a great experience.
We highly recommend her and the entire tour company team... super agents and people!
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