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Tuscany’s vineyards teach us that time is the finest winemaker



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Experience the essence of the Tuscan lifestyle on this Private Departure, based in a historic villa surrounded by rustic gardens and rolling countryside. This thoughtfully curated itinerary immerses you in the charm and character of the region, focusing on its acclaimed local wines, culinary traditions, and the leisurely pace of life that invites you to kick back and savor its simple pleasures.


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    Land at Florence-Peretola Airport and transfer to your exclusive villa nestled in the Tuscan countryside. Savor a wine-paired Welcome Dinner at the villa as you embark on your journey

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    After a relaxing morning at the property and al fresco lunch, venture out to a family run organic winery for a tour and tasting of Cortona DOC wines before continuing to the ancient hilltop town of Cortona

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    Head south to explore the tastes and treasures of Montepulciano— the medieval hilltown famous for its Renaissance architecture, stunning views, and Vino Nobile di Montepulciano

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    Indulge in a leisurely day at the villa, embracing amenities such as the outdoor pool, wellness area, and gardens. Roll up your sleeves for a hands-on cooking class this evening

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    DAY 5. SIENA

    Discover the UNESCO-listed medieval city of Siena on a guided walking tour of the city followed by free time to wander its winding cobblestone streets before returning to your villa

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    Make your way to the renowned Chianti Classico DOCG appellation for a winery tour and tasting followed by a lunch made from locally sourced ingredients

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    Today’s highlight is a picturesque boat ride on Lake Trasimeno with a stop on the island of Isola Maggiore. Enjoy free time afterward in the charming town of Castiglione sul Lago

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    Transfer to Florence-Peretola Airport for return flights home

Villa Accommodations

Villa Fonte Ripa 1

Situated in the heart of Tuscany, our featured villa offers a serene escape amid the rolling hills and lush vineyards of the region. The rustic elegance of the meticulously restored property blends traditional Tuscan charm with modern comforts.

The villa can accommodate 6 - 14 guests in a main house with expansive living spaces, spacious bedrooms with en suite bathrooms, plus a separate detached suite. Other amenities include air conditioning, Wi-Fi, and laundry.

Park-like grounds surround the villa, offering a variety of outdoor spaces, including an outdoor pool, covered terrace, barbecue area, grass fields suitable for soccer and volleyball, and beautifully-tended gardens. The property also features an air-conditioned fitness room, and spa with a jacuzzi, Turkish bath, sauna, and massage room.

Villa Fonte Ripa 1

"The planned trip was magnificent and exceeded our expectations everyday." - Becky L. [April, 2024]

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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.

Cortona has appeared in movies and TV

Cortona was the filming location for the movie "Under the Tuscan Sun," based on the memoir by Frances Mayes. The 2003 film showcased the town's beautiful scenery and charming streets, which helped to boost its popularity as a tourist destination. Many movie fans visit Cortona to see the locations featured in the film and to experience the authentic Tuscan lifestyle depicted in the story. In 2021, Cortona was also a filming location for scenes in two episodes of the HBO show Succession.

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.



$58,000 for 6 guests. For 7-12 guests, please contact us for pricing details.


  • 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

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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 

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