Classic Tuscany Itinerary

What to expect on this itinerary
Classic is another word for quality and charm, words that describe the splendor around you. Cafes set out tables alongside streets offering you a moment to yourself surrounded by indescribable history. Standing in front of Michelangelo’s David teaches you how to treasure a moment. Listening to the quiet passing of the Arno River provides a soundtrack to unforgettable memories. Your custom tailored 2020 Tuscan tour offers you the true meaning of classic, where no single image creates the wonders of the region. Instead, you find a unique combination of Tuscan experiences that shows why the word “classic” is synonymous with timelessness.
Customizable Itinerary
Florence - Light from the Shadows
Florence is home to dazzling art and superb culture, emanating from the cobblestone streets and classic architecture. Cafes line the banks of the Arno River. Palaces hide behind stunning gates at the heart of the city. Your private transfer greets you at the airport and escorts you into the historic city center. The splendor of the city is almost overwhelming.
The dome of the Duomo adds shape and dimension to the antique skyline of bell towers. In Santa Croce Church, the aroma of frankincense continues to waft up and down the nave. Giotto’s frescoes dating back to the 14th-century decorate the walls, depicting the life of St. Francis. Funerary monuments of Leon Battista Alberti, Galileo, and Machiavelli decorate the interior, including the tomb of Michelangelo, casting a long and inspiring reach on the arts of the city.
The laidback culture of the city brings to light the ideals of truth and beauty in art. The Accademia houses Michelangelo’s David, and Bargello Museum houses Donatello’s David. Both works of art are a testament to their time, marked with indescribable detail, and sensational in their size, able to tell an entire story in a single pose.
The scent of café con latte, or coffee with milk, fills the afternoon air. Bakeries display dwindling pieces of cake and cookies. It is easy to settle into the luxuries of the city cast in the preserved antiquity.
What's Included:
Florence - Enlightened Beginnings
Apuan Alps - Against the Apuan Alps
San Gimignano - Twin Towns
Siena - Pristine Past
Siena - Into the Palaces
Montepulciano - Slowly Finding Tuscany
Montepulciano - Renaissance Once More
Trip Highlights
- Discover the marvels of the often overlooked Bargello Museum, including the masterworks of famous artist Donatello
- Delight in a private tour of Florence that offers an in-depth view of the Renaissance city and its exceptional artwork, architecture, and history
- Explore the exquisite architecture of the medieval town of Lucca, known for its historic walls, and filled with architectural treasures you shouldn’t miss
- Witness the exceptional design and miraculously preserved Leaning Tower of Pisa
- Follow your guide on a tour of Siena to visit the treasured palaces and museums housing some of the region’s most inspiring history and frescoes
- Visit the headquarters of one of the oldest banks in the world
- Traverse the large and embracing grounds of the magnificent abbey of Monte Oliveto Maggiore
Detailed Description
Each village in Tuscany has a distinct character making it feel independent of its surroundings, yet somehow fit into the encompassing collective details of Tuscany. On your 8-day Tuscany tour through the celebrated Italian province of Tuscany, you will find hill towns and Etruscan ruins, art commemorating saints and poets, sculptures and stories. Marble churches act as signs of devotion, and historic ramparts continue to protect cities from outside influences. The enchanting qualities of Tuscany vacations take you beyond the surface and deeper into the cities that house history in the artwork and artwork in their history. When you arrive at Florence International Airport, your private transfer is ready to greet you.
You enter the Renaissance city of Florence and find the preserved splendor of the past emanating from the design and décor of the historic city center. The remainder of the day is yours to become acquainted with all Florence has to offer, from the images inside Santa Croce to the delicious restaurants on the opposite side of the Arno River, known as the neighborhood of Oltrarno. The following morning, your guide meets you at the hotel after breakfast ready to lead you through the marvels of Florence, including a guided tour of the celebrated Uffizi Gallery, providing insider details of the iconic and lesser-known works.
Venture outside of Florence to the city of Lucca, located at the base of the Apuan Alps. Step beyond the historic city walls for a tour of the Romanesque churches and exquisite tower overlooking the main square. A half-day tour of Pisa shows you the classic image of the city, the Leaning Tower. Then, go deeper into the city’s history with a visit to the National Museum. Later that day, you arrive in San Gimignano for a peaceful introduction to the quiet hilltop town. After breakfast, you can traverse the vibrant streets climbing up and down the hillside, and visit the tallest tower in the city.
Continue onward to the medieval city of Siena, where you can visit the famous Siena Cathedral in the afternoon. The following day, you can take your time traversing the sensational preserved streets of Siena, visiting lesser-known yet equally wondrous sites, around the cityscape. Venture through the Tuscan countryside, visiting the magnificent abbey of Monte Oliveto Maggiore, before enjoying a relaxing lunch in Pienza, and the rest of the day in Montepulciano. Your final day in Tuscany lets you spend some time in Montepulciano reveling in the quintessential Tuscan charm, down to the wineries encircling the city. Your private transfer meets you at your hotel in Montepulciano and escorts you to Florence International 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.
Verified Traveler Reviews
Based on 1242 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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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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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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The travel assistance from Zicasso's company was very helpful. All tour guides were wonderful, as well as the tours, with the exception of the all-day tour into Tuscany, ending in Siena.
As an elderly woman, I found it to be too long. Also, after the lovely lunch and wine tasting, it was difficult to go on a 3.5-hour walking tour, as well as walk a mile into Siena and a mile out of Siena. Also, the bus did not have great air conditioning and did not have a working bathroom.
The other issue I had was with the seven and nine flights of stairs in Venice and Florence in our hotels. With bad hips and knees, I was confined to going up and down the flights only once during the day. I suggest this be a question for guests in the future.
The travel company was very generous in paying for a wonderful dinner for me and my grandson due to my struggles.
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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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Overall, it was a very good trip. Zicasso’s trip planner was very responsive. In retrospect, I would have spent three days in Tuscany instead of six to see another area.
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