7-Day Off the Beaten Path Tuscany Vacation

Panoramic view of the Val Di Chiana in Tuscany, Italy.

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.

Countries Visited

Italy

Places Visited

Siena, Florence

Suggested Duration

7 Days

Customizable Itinerary

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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:

Transfer
Accommodation
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.

4.9

Verified Traveler Reviews

Based on 395 reviews

Italy Travel Review: Tuscany, Siena, Montepulciano, Pienza, San Gimignano, Florence, Farm-to-Table Experience, 6 Nights

We had a fantastic trip, all thanks to our travel specialist. We spent a few days in Siena, touring different Tuscan towns like Montepulciano, Pienza, and San Gimignano, and then we spent a couple of nights in Florence. All of our drivers and guides were very thoughtful that we had my two-year-old nephew with us.

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Italy Tour Review: Pompeii, Amalfi Coast, Florence, 12 Nights

Zicasso’s travel company and every single guide and driver were stellar. All four hotels were good or excellent. There was one error on the schedule for the day outside of Florence when we had a driver to take us to the Siena region. The schedule stated three hours, so we paid for tickets to the Pitti Palace/garden, which turned out to be wasted money as the driving tour was actually nine hours. It was a beautiful day, though.

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Italy Travel Review: Venice, Florence, Tuscany, Cortona, Sorrento, Amalfi Coast, Capri, Pompeii, Rome, Vatican, Lagoon Boat Trip, Wine Tasting, Cooking Class, 2 Weeks

Our 16-day trip through Venice, Florence, Tuscany, Sorrento and the Amalfi Coast, and Rome was outstanding in every detail. Every transfer ran on time, every guide was knowledgeable and warm, and every hotel was a great choice.

Our favorites were the private lagoon boat trip in Venice, the Brunello wine and cheese tour, the pasta class at a Tuscan farm, Pompeii, the Capri cruise, and the Vatican tour. We couldn’t have asked for better planning or support. We highly recommend Zicasso's travel company.

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Italy Vacation Review: Tuscany, Rome, Horseback Riding, 1-Week Trip

I had a wonderful experience working with Zicasso's travel specialist and the travel company for a seven-day trip through Tuscany and Rome.

What impressed me most was the travel specialist's flexibility and patience throughout the planning process. I changed the direction of my trip and my ideas multiple times, and each time she came back with thoughtful, tailored options that reflected exactly what I was looking for. Despite several revisions and a fairly last-minute planning timeline, she was able to secure all of the accommodations, activities, and logistics I wanted, while staying within my budget.

During the trip itself, the level of service was outstanding. The travel company stayed in touch via WhatsApp throughout my journey and sent daily reminders of the next day’s itinerary, which made traveling feel effortless and stress-free. Whenever I had a question, needed an adjustment, or encountered a minor issue, their responses were prompt, helpful, and professional.

The combination of personalized planning, attention to detail, and exceptional support during the trip made this a truly enjoyable experience. I have absolutely no hesitation in recommending this travel specialist and the travel company to anyone looking for a customized and well-executed travel experience.

Thank you again for helping create such a memorable trip!

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Italy Birthday Trip Review: Tuscany, Cinque Terre, Florence, Monterosso al Mare, Boat Ride, Wine Tasting, Cooking Class, Paper-Making Class, 10 Days

Zicasso’s travel specialist and her team crafted a wonderful 10-day trip to Tuscany, Cinque Terre, and Florence for my husband's 60th birthday. All the hotels were beautiful boutique hotels that we probably would not have found if we were planning it ourselves. The same was true with the experiences they booked for us. They have the local connections and can provide experiences you may not easily find by searching the internet.

We loved that our wine tastings were at smaller local wineries. All our guides were very friendly and very knowledgeable. All our drivers were always on time. They took care of reserving our train tickets, as well as dinner reservations. We felt very well taken care of throughout the entire trip.

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Italy Travel Review: Rome, Sorrento, Florence, Tuscany, 2 Weeks

Zicasso's travel company was beyond exceptional in the planning and execution of our customized 12-day trip to Rome, Sorrento, Florence, and Tuscany. From the creation of our initial itinerary through the entirety of our travels, they were extremely thoughtful and delivered incredible client service. Every activity, tour, driver, tasting, hotel, etc., planned by the team was amazing. We highly recommend the company to anyone interested in elevating their travel experience in Italy.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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