Reserve your own private departure with

Experi Logo


"My idea of heaven still is to drive the gravel farm roads of Umbria and Tuscany, very pleasantly lost." - Frances Mayes


Guest limits

8 / 7

Days / Nights


Starting Rate Per Person
(Minimum 4)

Indulge in the ultimate Tuscan adventure on this Private Departure exploring the vineyards  and villages around medieval Cortona. Discover local culinary traditions, savor the region's distinctive wines, engage in a truffle hunt, and experience the iconic architecture of Siena and the beauty of Lake Trasimeno. This carefully curated itinerary combines the best of gastronomic delights, scenic landscapes, and cultural and historic exploration, promising an unforgettable journey in the heart of Tuscany. 


  • Experi_LogoSymbol


    Land in Florence or Perugia airport and transfer to accommodations in Cortona

  • Experi_LogoSymbol


    Lunchtime cooking class and walking tour of the medieval hilltown of Cortona

  • Experi_LogoSymbol


    Wine estate tour and tasting followed by visit to picturesque Pienza

  • Experi_LogoSymbol

    DAY 4. Etruscan Hills

    Exploration of Tuscan hidden gems including special dinner at Michelin-starred restaurant

  • Experi_LogoSymbol

    DAY 5. Siena

    Wine estate visit and light lunch followed by guided tour of historic Siena and dinner on terrace of a private place

  • Experi_LogoSymbol


    Boat ride on beautiful Lake Trasimeno including stop on the island of Isola Maggiore; Lunch and free time in the charming town of Castiglione sul Lago

  • Experi_LogoSymbol


    Morning agriturismo visit including truffle hunt and lunch; evening farewell dinner

  • Experi_LogoSymbol


    Transfer to Florence or Perugia airport for return flights


Fonte al Vento Villa 2

Fonte al Vento Villa

Nestled among olive groves and vineyards, this boutique accommodation provides a charming retreat in the picturesque Tuscan countryside. Just a short walk from the town of Cortona, the villa offers an authentic Italian experience, offering traditional architecture, elegant interiors, and postcard views of the surrounding area. The property features two outdoor pools, restaurant, bar, garden and terrace, and complimentary Wifi. Rooms are equipped with air conditioning, tea/coffee making facilities, and bathrooms containing toiletries and hair dryer. While staying at the villa, guests also have access to a lounge area, fully-equipped kitchen, and washing machine.

Fonte al Vento Villa 2

"In Tuscany, the landscape is a masterpiece painted by nature's brush, and its vineyards produce wines that are poetry in a bottle." - Ernest Hemingway

Get Started

Fun Facts

Lago di Trasimeno is Italy’s fourth largest lake

The lake covers 126 square kilometers and is rather shallow with a maximum depth of 6 meters. It is located in Umbria, at an altitude of 257 meters above sea level and has three islands, Isola Maggiore, Isola Minore and Isola Polvese. The lake has a diverse flora and fauna with a wide range of birds and an abundance of fish. It is also renowned for its beautiful sunsets and tranquil waters.

There is a barrel rolling competition in Montepulciano

The yearly Bravio delle Botti or barrel rolling competition is held in the historic center of Montepulciano on the last Sunday of August. The eight contrade, or districts of the town - Cagnano, Collazzi, Le Coste, Gracciano, Poggiolo, San Donato, Talosa and Voltaia - compete against each other by rolling empty wine barrels weighing about 80 kg up the hill for over one kilometer. The race dates back to the end of the 14th Century but in 1974 horses were replaced by barrels.

Pienza is considered the capital of Pecorino cheese

Pecorino is made from ewe’s milk, its name is actually derived from pecora the Italian word for sheep. Pienza produces high quality Pecorino cheese, the milk comes from the sheep grazing in the preserved Val d’Orcia landscape, where grass and aromatic herbs grow in the meadows. This unique terroir gives the Pecorino di Pienza cheese its distinctive flavor. Every first Sunday in September, you can witness the town’s six districts compete against each other in a cheese rolling game, iI Gioco del Cacio al Fuso.

There is a network of underground aqueducts under the town of Siena

The network stretches over 25 kilometers and provides water to the springs and wells across the city. Known locally as the Bottini, the network was created sometime between the 12th & the 15th Century to bring water to the town. There are two main branches spread on two different levels. The Bottino maestro di Fontebranda is the oldest and deepest tunnel and carries water from Fontebecci to the Fontebranda Fountain. The Bottino maestro di Fonte Gaia is more recent, longer and shallower and brings water to the fountain Fonte Gaia in Piazza del Campo.



  • Accommodations during program dates, including all taxes and fees
  • All activities and private excursions described in the itinerary along with services of local guides, entrance fees, and private transportation
  • Meals as detailed in your itinerary, including pre-arranged drink pairings
  • Private airport transfers with porterage on the first and last scheduled days of the program

Not Included

  • Airfare to/from arrival and departure cities
  • Travel insurance
  • Additional alcoholic beverages beyond what has been arranged by Experi to pair with the included major meals
  • Gratuities for drivers, local guides, porters, and included meals

Travel Insurance

Learn more about travel insurance and how it can help you prepare for the unexpected at

Travel Terms & Conditions

View our complete terms and conditions here at

Reservation process

Step 1:

Complete the form above indicating:

  • the number of travelers in your group
  • your preferred travel dates
  • the best way to reach you

Step 2:

We will contact you to discuss your preferences.

Step 3:

Based on our conversation, we will check availability, confirm pricing, and provide you with a detailed proposal.

Step 4:

To confirm the services and accommodations for your private departure, a non-refundable 50% deposit of the total trip fee is required.

Frequently Asked Questions (FAQs)

How a Private Departure Works:

A Private Departure is a program that our destination specialists have meticulously crafted and curated to highlight the best of a particular destination. While we offer a few options to personalize your journey, the main framework of a Private Departure itinerary has been set. If you are seeking to make changes in the schedule or activities, a Custom Program may better suit your needs.

Destination-Specific Information - Tuscany:

This trip appeals to food and wine enthusiasts seeking to become immersed in all the storied region of Tuscany has to offer including culinary traditions, exceptional wines, colorful history, and picturesque landscapes.


P.O. Box 10576
Bainbridge Island, WA 

IATAN logo grayeota logo grayATTA Member


Join our newsletter