Historical Immersion Tour of Tuscany: Siena and Florence

What to expect on this itinerary
The alluring heritage of Italy immerses you in its captivating art, intricate architecture, and delicious during this historically-based 7-day Tuscany tour. Bask in the picturesque views of iconic Tuscan landscapes that feature sprawling vineyards, towering cypress trees, and rolling hills, and medieval villages. Whether sipping celebrated wines or viewing priceless Renaissance art, your Tuscany tour will reveal in the region’s illustrious past.
Customizable Itinerary
Siena – Introductory Tour of the City
Siena acts as a preserved masterpiece that represents Tuscany, Italy, and the power of individual city-states. Your private transfer will greet you at Florence Peretola International Airport and escort you to your accommodations in the heart of Siena. After settling in to the comforts of your accommodation, your guide will introduce you to the marvels of the city. Your tour will begin at Piazza del Camp and will include the Duomo. After your tour, you will have the remainder of the day to spend at your leisure.
What's Included:
Siena – Antique Towns and Wine
Siena – The Val d’Orcia Wine Region
Florence – Power, Prestige, and Preservation
Florence – Renaissance and Medieval History
Florence – Discovery of Florence’s Past
Florence – Departure
Trip Highlights
- Discover the secret history of San Lorenzo Church in Florence by finding hidden sketches from Michelangelo
- Embrace the charms of Montalcino during a private tour of the Val d’Orcia with a wine tasting inside an antique wine cellar
- Witness the treasured sinopie of Pisa’s Sacred Fields that reflect the original sketches of master artists
- Delight in the enchanting ambiance and welcoming locals of Greve in Chianti during a private tour
- Wander the winding cobbled lanes of Lucca to explore the exceptionally preserved antique walls and Guinigi Tower
- Enjoy the point at which history and artistic mastery converge in the Uffizi Gallery
- Revel in the grandeur and romantic atmosphere of the Renaissance town of Pienza, which is the former home of Pope Pius II
- Bask in the majesty of Florence’s Duomo during a private tour
Detailed Description
Your 7-day Tuscany tour will combine the marvels of the region’s natural scenery with its splendor of preserved towns and cities. This tour will include private transfers, specialized guides, and unique discoveries. Whether you prefer to linger in the medieval charms of Siena or to explore the often-overlooked museums of Florence, you will have an immersive and authentic experience.
Your historically-based tour of Tuscany will begin with your arrival at the Florence airport, where your private transfer will greet and transfer you to your accommodation in Siena. Here, you can enjoy the medieval ambiance with an introductory tour. A specialist guide will lead you through the Chianti Region and the Val d’Orcia for introductions to the landscapes. You will visit enchanting towns, such as Pienza and Montalcino, to witness the preserved lifestyle of Tuscany’s tranquil villages and to sample remarkable wines, such as Chianti Classico.
You will then transfer to Florence for three nights. Your time here will begin with a fascinating exploration of Pisa and Lucca with a specialist guide. The distinctive cities will reveal their former power dynamics and artwork, from Pisa’s famous Leaning Tower to the dramatic walls that surround the city center of Lucca. Once you have settled into the beauty of Florence, you will have two full days to uncover the artistic treasures of the city, from the Uffizi Gallery to the San Lorenzo Church. Lastly, your private transfer will meet you at your hotel in Florence and escort you to the airport for your flight home.
Starting Price
$3,200 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 216 reviews
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We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.
I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.
Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.
As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.
I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.
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From the moment we began working with Zicasso's trip planner, our every need was met. He listened and planned an epic trip based on our conversations. Then, for our trip, we worked with another trip planner who was extremely responsive and professional, especially when we were in Italy. Any questions we had were promptly answered. Everything they planned was pure luxury and fantastic. The private pick-ups, drivers, and tour guides were absolutely prompt and fantastic. Every tour was super-fun and informative. Highlights included the wonderful hotels, food tour in Florence, tour in Venice, cooking class, and tasting track in Tuscany. I would highly highly recommend. It was a five-star, wonderful trip!
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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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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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