A Tuscan Dinner Party for 4

an Experience-Based Package

Package Includes:

  • 5-night stay for 4 people in a historic 2-bedroom, 2-bathroom apartment in central Cortona

  • Your choice of EITHER a private multi-course traditional Tuscan dinner prepared by a local chef in the comfort of your home paired with a selection of regional wines OR, a multi-course dinner at a renowned Cortona restaurant

  • Tuscan wine sampling and antipasti at a family-run enoteca in Cortona

  • 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 Gabriella and Casa Angelico

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

Join us in Cortona, one of Tuscany’s ancient Etruscan hill towns, with its picturesque medieval buildings and spectacular vistas of the Val di Chiana and beyond. Cortona is perfectly situated to explore all the rich culture that Tuscany has to offer: gastronomical delights, world-class wines, Renaissance art, historic architecture, the generosity of the Italian spirit and so much more. Come create treasured Tuscan memories that will last a lifetime! 

Spend 5 nights in the enchanting Tuscan town of Cortona staying in a beautifully-curated 2-bedroom, 2-bathroom apartment for 4 people, 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 a full kitchen, wifi, washing machine, 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 tasting legendary Tuscan wines and 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.

You will have the choice of enjoying an authentic Tuscan multi-course dinner prepared for you in the comfort of your Cortona home by one of our talented Cortonese chefs or of dining out at one of our favorite Cortona restaurants, Ristorante Il Cacciatore, where you will be treated with a multi-course dinner. Delight in experiencing the flavors of Tuscany, which will start 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 excellent local wine will, of course, be provided. Special dietary needs can be accommodated if necessary. Buon appetito!


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.


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