Indulge in the beauty of rolling hills and iconic rows of cypress trees that lead to charming medieval towns during this custom-tailored 7-day Tuscany tour. Whether sampling the remarkable flavors of local wines or basking in spectacular views, you will travel away from the trodden path to immerse yourself in authentic towns, unique traditions, and customary flavors that have been preserved through time.
Customizable Itinerary
Day 1
Siena – Culinary Introduction to Tuscany
Your flight will land at Florence Peretola International Airport, where your private transfer will meet you upon your arrival. You will arrive in Siena with time to settle into the comforts of your luxurious accommodation. The 12th-century tower of Torre del Mangia reaches nearly 289 feet tall and looms over the main square of Piazza del Campo. You can visit a traditional garden, where the residents tend to vegetables, goats, geese, and chickens. Here, the chefs create traditional local cuisine using only local and seasonal flavors, providing you with a fabulous introduction.
What's Included:
Day 2
Siena – Enjoy Art and Medieval Towns
Day 3
Siena – Murlo, Arezzo, and Val di Chiana Aretina
Day 4
Siena – The Coastal Wine and Olive Oil Route
Day 5
Siena – Monticchiello, Pitigliano, and Sorano
Day 6
Florence – Off-the-Beaten-Path Tour of Florence
Day 7
Florence – Departure
Trip Highlights
- Embrace the gorgeous flavors of traditional Chianti Classico when sampling wines around the medieval town of Montefioralle
- Discover the marvels of Florence from a different perspective and uncover the hidden gems of the city
- Uncover Etruscan artifacts when visiting the Val di Chiana Aretina
- Sample the marvelous wines known as Super Tuscans in the hilltop town of Bolgheri
- Bask in the beautiful canals and charming café culture of the seaside town of Livorno
- Embrace the marvelous and historic tastes of a Jewish dessert known as sfratto dei goym
- Witness the striking plays of the Teatro Povero when visiting the town of Monticchiello
Detailed Description
You will have an immersive experience during this 7-day Tuscany tour. This off-the-beaten-path adventure provides you with luxury, specialist guides, and private drivers. Tuscany possesses an abundance of hidden gems that are often overlooked for the more famous destinations. Traveling away from the known cities and worn paths will provide you with pleasant surprises, such as authentic cuisine, cobblestone lanes that have remained unchanged since medieval times, unique canals, and natural wine cellars.
Your Tuscany tour will begin with your arrival at Florence’s international Airport, where your private transfer will escort you to the city of Siena. You will have time to get acquainted with the medieval city before embarking on an introductory tour that will lead you to a dinner of delicious fare. You will have five nights in the city, and you will use it as a base to explore the larger variety of Tuscany’s landscape and culture. Your private driver will lead you to old towns near the edges of Florence to find incredible artwork and heritage that has been hidden in the shadows of Tuscany’s capital. In the hilltop town of Montefioralle, you can wander along the cobblestone paths and sample the incredible flavors of Chianti Classico.
The following day, you will find the pre-Roman history of Tuscany on display beneath the medieval foundations of the towns of Murlo and Arezzo. Spending time on the Etruscan Coast will take you from Livorno to Piombino, where you can sample the elegant flavors of Super Tuscans and savor the distinctive flavors of local olive oils.
The medieval towns of Monticchiello, Pitigliano, and Sorano will offer unique insights into the culture and history of Tuscany, ranging from a historic theater to a unique Jewish heritage. You will then transfer to Florence, where a private tour of the city will reveal art and culture outside of the famous museums.
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.
Reviews of Zicasso's Referral Service
4.9 stars based on 5871 reviews.
Zicasso's travel agent created an itinerary and experience that was simply perfect. Every hotel experience, guide, and driver was excellent. She was kind, patient, knowledgeable, and made the perfect suggestions. I loved working with her! Thank you to our agent, the tour operator, and Zicasso for a wonderful trip!
Reviewed By Anita L.
The trip was wonderful. Zicasso's travel agent and her staff planned the perfect 10-day trip. The accommodations, the drivers, the guides, and the restaurant recommendations were perfect. The communication was excellent and timely. They went above and beyond to make sure we were comfortable and happy. The staff were very attentive and flexible, even when we wanted some small changes, such as pick-up times for the drivers. They adapted and made it all work. This travel agent is absolutely terrific.
Reviewed By Marci M.
Our Italy trip with Zicasso’s travel partner was nothing short of spectacular! Referred by a friend who had an amazing experience, we decided to give it a try and were not disappointed. Our agent was fantastic, always ready with answers to our questions and providing excellent support throughout our journey.
In Tuscany, we visited beautiful wineries and enjoyed a delightful lunch with the vintners, who were incredibly warm and welcoming. Her attention to detail was evident when she adjusted our plans due to weather changes and even checked in on us when we were slightly delayed for a tour.
Siena was breathtaking and our hotel in Rome was perfectly located, allowing us to walk to all the major sites. One of the highlights was a small boat tour around Capri from Amalfi—perfect weather and stunning waters made it unforgettable. The cooking class on the Amalfi Coast, set on the side of a cliff, was exceptional and having personal tours just for the two of us was an unexpected and delightful bonus.
We can't express enough how much we enjoyed our Italy trip. The travel partner exceeded our expectations and we highly recommend them for a truly memorable experience!
Reviewed By Kent S.
Zicasso’s trip coordinator and her team did a fantastic job, not only in planning the trip to meet our needs and wants, but also in personalizing it as needed. They were also available as we needed them to adjust things, such as pickups, and even made some dinner reservations for us. With our budget, they set us up in excellent hotels that fit our desire for the trip to be a wonderful anniversary getaway. Her staff were also very helpful. We would strongly recommend them for a trip to Italy!
Reviewed By Rajesh J.
Zicasso's travel planner and her staff did a perfect job for our family of six. She made our trip seamless!
Everything she planned was perfect and no detail was left out. I would use them again and again for my travels to Italy.
Reviewed By Sally F.
My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.
Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.
Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.
Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.
What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.
Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.
As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.
Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.
The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.
This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.
Reviewed By tasmia S.
