Take advantage of a rare opportunity to replace the maddening crowds of the Tuscan tourist trails with, among other exclusive experiences...

a cooking class on a private wine estate,

   a delicious adventure through a kiwi farm,

       the chance to scale medieval towers,

           and a journey back in time through incredibly                         preserved Etruscan ruins,

This is the Tuscany that you truly dream of, expertly planned for your effortless enjoyment.

Timeless Tuscany 

Timeless Tuscany 

You will be staying in magical Siena and charming Lucca, while you explore the timeless treasures of this incredible region. 

Home Away From Home

Spend a full day exploring the picturesque landscapes and charming small villages of the Val D'Orcia, according to your personal preferences and preferred pace. 

Whether you choose to linger all day in one place or hike or drive your way between several, this entire portion of your trip is devoted to a sense of belonging to the land and the local way of life.   Peaceful, easy,  restorative, and entirely as you like.  Welcome to the Val D'Orcia! 

Just like our city based walking tours, these day trips are entirely private.

 With a private driver at your service all day & local experts waiting to meet you in each new destination.   
Most day trips take place over the course of anywhere from 6-12 hours, starting and ending at the door of your hotel.

 Nothing to navigate, nothing to worry about.  Just pure comfort and convenience from start to finish.

The Untouched Hills 

An undisputed favorite of our clients.   Begin by venturing into the famed wine lands of Chianti with the services of your private driver - effortlessly avoiding the numerous tourist traps. 

Once you have arrived on the family run wine estate, acclimate with a private tour of  the grounds and enjoy the wine tasting that follows.  Then, for the main event: gather in the kitchen for a cooking class of regional specialties.   You'll celebrate your hard work by diving into the multiple courses right after, enjoying a lunch to remember forever!

Travel back in time today to the fascinating Etruscan era where you will discover a highly developed and yet somewhat mysterious ancient civilization - that  actually predates the Romans!

From the stunning ruins found in the pastoral countryside, to a world renowned artifact exhibit, this one of a kind day will be topped off with the invitation to try your hand at carving alabaster with a local master! 

Today is a true adventure - combining a visit to an unspoiled medieval hamlet complete with a castle and scalable walls, an olive oil and kiwi (yes, kiwi!) farm, and a visit to one of the most iconic architectural masterpieces of all of Italy surrounded by countless hidden gems.

It's non-stop fun from start to finish and with the services of private drivers and guides, all that is expected of you is enjoy each moment and change of scenery to the fullest.

Cooking in Chianti

Antiquity & Alabaster

Countryside Surprise

Private Day Trips

Every Select Portfolio Collection itinerary is able to be further customized to your personal tastes, preferences, and interests.   

Here are just a few of the endless options we can offer through our hand-selected network in this region.

Half or full day organic food and wine experience in Sienese countryside

Additional private cooking classes or wine tastings

Visit to local artisan studios or farms

Day trip to the Carrara marble quarries  or Cinque Terre

Many, many more!

Options & Upgrades

Italiana Travel Design is happy to make hotel arrangements for you.  We are also happy to work with you if you prefer an alternate accommodation option, such as  private vacation rental (i.e. AirBnB, HomeAway, VRBO, etc.) or to stay with your friends or family.   

We believe everyone should travel as they truly prefer.

To begin your reservation request for Timeless Tuscany, or for additional information, please click here.

To view additional Tailored Travel options in our current Select Portfolio Collection, please click here.


Transfers & Transportation

As with all Italiana Travel Design itineraries, private transfers or transfer support are included upon arrival and departure. 

All additional transportation in this itinerary is provided by a private driver. 

Our 10 day Timeless Tuscany Itinerary starts at $5,920.00 per person, including accommodation.

Dates & Availability

Italiana Travel Design does not have set departure dates or blackout dates.

While each individual experience is subject to availability, a full length itinerary is always possible for your preferred dates, including during major holidays. 

Total Travel Days

This itinerary has been designed for a total of 10 days in Italy.  Your first day will be your day of arrival and your last, your day of departure.  Two fully free days are typically included in this itinerary design.

Combination & Customization

Selected days from this itinerary are able to be combined with selected days from other Select Portfolio Collection itineraries.  For those looking for a three week trip or more, the entire itinerary can be combined with another entire itinerary.

The inclusion of two free days and the overall flexible nature of the majority of the itinerary inclusions also allow for unique customizations, should you be interested in one or more.