7-Day Off the Beaten Path Tuscany Vacation

What to expect on this itinerary
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
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:
Siena – Enjoy Art and Medieval Towns
Siena – Murlo, Arezzo, and Val di Chiana Aretina
Siena – The Coastal Wine and Olive Oil Route
Siena – Monticchiello, Pitigliano, and Sorano
Florence – Off-the-Beaten-Path Tour of Florence
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.
Verified Traveler Reviews
Based on 3450 reviews
It was a fantastic trip. Everything we planned with Zicasso’s travel company was on time and with high-quality local guides and drivers. They were very responsive and helped us build an itinerary for our 12-day trip to southern Italy. They stayed in touch throughout the planning process, helping us find restaurants and answer questions. I would highly recommend this travel company to anyone planning a trip to Italy.
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Zicasso’s travel specialist was a pleasure to work with. She helped me plan our trip of a lifetime to Italy. I told her which cities we wanted to visit and our interests, and she gave me great recommendations for tours and experiences. She was flexible with the itinerary changes I made beforehand and, after our arrival, the pre-arranged transportation was seamless and the hotels were great.
Our ambassador during the trip was very responsive when I had questions. I appreciated the daily messaging app reminders for the times and activities for the next day, including a location link on Google Maps for the meeting points. Our pre-arranged drivers and tour guides were excellent.
This holiday was everything I hoped for. If I am fortunate enough to plan another holiday to Italy, I will definitely use the travel company again! Based on this experience, I will definitely use Zicasso again for an international holiday.
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We had a great trip to Florence, Tuscany, and Rome. One of the best parts about the trip was our travel company. Zicasso's travel specialist took care of booking everything we needed and doing so within budget. I didn't have to worry about keeping up with tour tickets and schedules because he had already taken care of all that. He was also available for quick questions and updates while we were on our trip. We couldn't have asked for better!
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Zicasso set us up with a wonderful travel agent. The process of choosing and communicating through the Zicasso system was easy and helpful.
The travel specialist and her team planned a wonderful 15-day trip, with nine days in Rome and four days in Florence. She found us great accommodations that included a kitchen, which was a must for us. Other travel agents were not able to provide such accommodations.
The drivers we had were professional and picked us up on time. The guides were experts in their field and generally had taught at universities. The guides were very personable and tailored the tours to our interests.
She arranged all the necessary skip-the-line tours. We went to the Vatican with three different tours: the Sistine Chapel, the Gardens, and the necropolis to see St. Peter's tomb.
There were a couple of hiccups in this perfectly planned itinerary. Each time, the travel specialist and her staff were immediately available and guided us through solutions, such as trying to get to the Colosseum during the Roman Marathon.
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Zicasso’s travel company was highly responsive and understanding of what we wanted to experience and used their expertise to steer us to the best people and locations possible.
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We enjoyed our trip so much. Everything was planned well and on time in Italy! Zicasso's travel company did everything to help us with our trip interruption due to flight delays for weather here in the US! All the communications we had with them were spot-on.
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