Walking & Wine for 2

an Experience-Based Package

Package Includes:

  • 5-night stay for 2 people at the luxurious Casa Bianca just steps from Cortona. The newly renovated home features a private sauna.

  • Historical Walking tour of Cortona with an expert local guide

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

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

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

  • 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 Italian spirit and so much more. Come create treasured Tuscan memories that will last a lifetime! 

Spend 5 nights in a beautifully curated, Casa Bianca. The home is just 10 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, wi-fi, washing machine, and heating *Heating incurs an extra fee based on usage, to be paid at the end of your stay. 

You’ll experience the magic of Cortona with a 2-hour historical walking tour through the town led by an expert guide who imparts their knowledge of this fabled Tuscan hill town. Your tour will finish up at an internationally renown boutique located in a stunning ancient olive oil mill on the ground floor of a historic palazzo, where you will be welcomed with a special aperitivo – a glass of Prosecco with their signature floating edible gold and silver leaf flakes – while being guided through the artisanal jewelry making process.

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.


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 Information:

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

  • Reservations are based on availability. 

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

  • Airfare and ground transportation 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.