A Taste of Cortona for 2

an Experience-Based Package

Package Includes:

  • 5-night stay for 2 people in a historic 1-bedroom, 1-bathroom apartment in central Cortona

  • A multi-course Tuscan meal for 2 at a renowned Cortona restaurant. Made with seasonal, local ingredients and paired with an excellent regional wine followed by an artisanal dessert. *Reservations can be made upon request via our local concierge service.

  • Or, a choice of an in-home chef dinner with multiple courses and wine

  • Sampling of world-famous Tuscan wines and delicious antipasti bites at a family-run enoteca.

  • Expert trip planning assistance and local Cortona concierge service to assist guests in planning additional tours, experiences, and other aspects of their stay

  • Exclusive access to Stacey and Rob’s Insider Tips to Cortona

  • Accommodations included in this package: Casa Sabrina, Casa Antonella, Casa Adelina, and Casa Franca

  • There is also an option to upgrade to a larger accommodation if you’d like to add additional guests

Spend 5 nights in the enchanting Tuscan town of Cortona staying in a beautifully curated 1-bedroom, 1 bathroom flat just minutes by foot from the historic center of Cortona, where you will find restaurants, cafes, boutiques, world-class museums, and Renaissance churches, as well as incredible walks throughout the town and the surrounding countryside. Basic amenities include Wi-Fi, a coffee maker, and heating and air-conditioning. *Heating and air conditioning incur an extra fee based on usage, to be paid at the end of your stay.

Immerse yourself in a quintessential tasting room steps away from Piazza Della Repubblica in central Cortona. At this charming cantina, you will delight in sipping legendary Tuscan wines while savoring a selection of homemade antipasti. A wine expert will guide you through a journey of diverse wines from one of the most iconic wine regions in the world.  You will conclude this delightful tasting with a special gift reserved for our guests to enjoy in your Cortona home.

Lastly, you will have a choice of an in-home chef dinner or, enjoy an elevated Tuscan meal at one of Cortona’s oldest family-run restaurants. Your experience starts with an antipasto appetizer course, followed by a primo (typically a pasta course), after which comes the secondo, or meat course, and finally, the dolce, or dessert. An aperitivo drink of Prosecco followed by an excellent local wine will also be served.

Buon appetito!

*Special dietary needs can be accommodated upon request.


About our Insider Tips: Having lived in Cortona for over 20 years, Sojourn Ventures founders Stacey and Rob have created their highly acclaimed Insider Tips, an exclusive guide for our guests that provides tips about our favorite shops, restaurants, cafes, and other activities to experience in Cortona. Using this guide can give you a more personalized experience that goes above the standard tourist level, especially when you mention that you are “Friends of Stacey and Rob.” 


Additional Details:

  • Welcome packets will be emailed to winners upon notification of their purchase.

  • Reservations are based on availability. 

  • Package is valid for 2 years from the date of purchase. 

  • Airfare and ground transportation are not included. 

  • All Sales are final. There are no cash refunds. Packages cannot be resold to a third party. 

  • Photos provided are actual images of the private homes pictured. In the rare event that a home is no longer available due to circumstances beyond our control, force majeure, property damage, and/or change of ownership, Sojourn Ventures reserves the right to replace it with a home of equal value and quality. 

  • In the event that an experience is not available, Sojourn Ventures reserves the right to replace it with an experience of equal value and quality. 

  • CANCELLATION POLICY: Cancellation before arrival may be subject to forfeiture of reservations and funds.