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

7-Day Off the Beaten Path Tuscany Vacation

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Customizable Itinerary

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

Countries Visited


Places Visited

Siena, Florence

Suggested Duration

7 Days

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

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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

$2,501 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.

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