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 3461 reviews
Our honeymoon trip to Italy, planned by Zicasso’s travel company, was the perfect trip in every way. From the time we landed in Rome and were greeted by our driver to the time we left Venice 12 days later, every detail was taken care of. The guides, tours, accommodations, restaurant recommendations, and travel transfers were expertly executed, so we didn't have to worry about anything except having the time of our lives!
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The trip was amazing and the tours and hotels were great. We enjoyed every minute.
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Zicasso’s travel specialist made this our best trip ever. She was communicative and accommodating, as well as always available for our questions. Every tour and every guide was exceptional. Their ability to communicate their enthusiasm and passion was jaw-dropping. We came back each day with our mouths dropped by the amount of information and the fun we had. Each hotel the travel specialist picked for us was great, offering the best locations and caring, accommodating staff. She was a lovely and genuine person.
One of the highlights was our cooking class with a chef. This does not diminish each tour guide; they were perfect. Also, she arranged private transport that made our trip a breeze from beginning to end. Especially cool was the taxi in Venice! Thank you, to our travel specialist and Zicasso, for an amazing vacation. Oh, the wine and olive oil were perfection. Highly recommend!
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Our travel company and Zicasso were truly excellent trip resources and designers of our two-week vacation to Greece. They arranged every detail. We had transportation prearranged, lodging that was extraordinary, and food that was unforgettable.
Our guides for various day tours in each location were phenomenal. They were never rushed and seemed to give us limitless time. They made arrangements for us that were not part of their paid services, just because they were so welcoming. The guides were all graduates of universities who had completed months of additional studies to become certified as guides. We learned so much from our trip about the places, but also about the culture and what it's like to actually live in Greece. Bravo!
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Zicasso and our tour operator were both so easy to work with. We were a fairly large group (eight adults) and they did everything they could to accommodate and create a vacation to Italy that we will remember forever.
The communication was always prompt and efficient. They went out of their way on several occasions to accommodate changes and/or personal preferences during the planning process. We are so very grateful to Zicasso and the tour operator for helping us plan our perfect family vacation!
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Our Italy trip was so wonderful. From start to finish, Zicasso’s travel specialist curated a memorable and very special, life-changing experience. Our itinerary was amazing, thoughtfully planned (full, but not overwhelming), fun, and precise. We had great small/private tours and guided adventures, from wine tastings and a cooking class to historical explorations, with introductions to local cultural activities and immersion experiences. The attention to detail for the train and other ground transportation we needed during our daily trips was impressive.
I would highly recommend our travel specialist, the travel company, and Zicasso to assist you in planning your next trip/journey/adventure if you want an exceptionally individualized, unique, and special travel experience that will provide you with great, lifelong memories.
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