An Evening with Chef Ivan:

A Culinary Celebration for 6

an Experience-Based Package

Package Includes:

5-night stay for six guests at the exquisite Casa San Francesco
Private, in-home, multi-course Tuscan Cooking Class with Cortonese Chef Ivan Italiani
Exceptional guest services with personalized support tailored to help you plan and enjoy local activities. Our local team, with an office in the town square, is ready to assist with any in-travel needs. Whether you’re looking for recommendations for dinner or planning last-minute experiences.
A welcome gift awaits your arrival, featuring a bottle of wine and a selection of small provisions to help you settle in and begin your stay on the right note.
Exclusive access to Stacey and Rob’s Insider Tips to Cortona

Stay at Casa San Francesco, a beautifully restored 500-year-old home in upper Cortona. Featuring three spacious bedrooms and two full bathrooms, the property exudes traditional Tuscan charm. You'll find a cozy living area on the main floor and a fully-equipped Tuscan farmhouse kitchen, perfect for gathering. The primary bedroom offers privacy on its own wing, while the top floor boasts two double bedrooms and a shared full bath. Just a 5-10 minute stroll to Piazza della Repubblica, this home provides the ideal blend of tranquility and authentic Italian decor.

Meet your host, Chef Ivan, the heart and soul behind Casa San Francesco and a true master of Italian culinary artistry. Ivan’s warmth and hospitality are unmatched, making every guest feel like part of the family. Upon your arrival, you’ll be greeted with a delightful homemade treat—a cake lovingly baked by him. During your stay, take part in an intimate, hands-on cooking class led by Ivan, where you'll learn to craft traditional Italian dishes using fresh, local ingredients.

The experience concludes with a shared dinner, a joyous celebration of the flavors you’ve created together. For many guests, this heartfelt evening is the highlight of their journey—a genuine slice of Tuscan life that goes far beyond the typical tourist experience.

Immerse yourself in the rich traditions and flavors of Tuscany, guided by the passion and generosity of chef Ivan, who treasures every guest who steps into his home. This culinary escape will undoubtedly become a cherished memory of your Italian adventure.

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 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.
All utilities are included in this package. Guests do have to pay a mandatory tourist tax upon arrival directly to their host.
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 provide a private home and experience 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 prior to arrival may be subject to forfeiture of reservations and funds.

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What our Guests are Saying

“My family and I had the chance to stay in one of Sojourn Venture's fabulous Tuscan villas over the holidays. Our experience was nothing short of magical - from a private 5-course cooking class with Chef Ivan Italiani, to a day of touring Montepulciano and wine tasting with sommelier Francesco at two women-owned wineries, to a day trip to Deruta to visit ceramic factories, our time in Cortona and Tuscany was unforgettable. Stacey, Elizabeth and the entire Sojourn Ventures partners on the ground in Italy and Bali make it happen. Grazie mille!”
-Nelson J.
“We had such a wonderful time at the Casa San Francesco! We loved the house - it had so much personality and connection with culture. Very comfortable and had everything we needed. We arranged for the cooking class with Ivan and Fillipo and that was really special - we all learned new techniques and so enjoyed the conversations and experience. Sojourn went way out of their way to accommodate the many twists and turns for us to make this trip happen and we're truly grateful. We can't wait to go back!”
-Lynne G.
“The team at Sojourn was great - they immediately answered my questions and helped us be proactive as we put together a plan and started our travel. The Cortona guide is amazing and it’s the truth! You need to book the restaurants and those train doors really do close after 60 seconds!
Several things stand out about this trip:
Ivan’s cooking class was an experience my family wouldn’t have agreed to if it was in our hometown. We all loved it so much, and he is one of the nicest most gracious people ever.
The shops, bars and restaurants - while it took a minute to get used to the times the shops were open and closed, we had a fabulous time making our way around and sampling a little bit of most everything. Even being there almost a week, we didn’t make it to every place! It’s bigger than it seems!
Francisco’s winery tour was another highlight. We learned so much in a half day and are grateful for that opportunity. The only feedback I have there is that guests need some idea of what’s happening. We didn’t know if we were inside or outside, how far we were going, etc. It was freezing cold and raining that day, and we left one of our family members behind to study. It made me unnecessarily anxious. I will add that although we didn’t have to buy the wine, there seemed to be an expectation that we would. When we decided on a case, we were encouraged to buy more. While the prices and wine are outstanding, shipping charges make it not such a great deal.
The house was lovely - truly authentic. That view was stunning and our (adult) children took a million instagrammable photos just from the kitchen! The house was stocked with everything we needed which was wonderful for preparing meals.
And finally, those walking trails! Wow! We spent as much time as possible outside and our walks were absolutely incredible and memorable. We will never forget this trip and we are so pleased that it was there, in Cortona, a place we never knew existed several years before.
Thank you again for the opportunity to provide feedback. We will happily share our experiences with anyone who asks. Happy holidays to you and everyone there at Sojourn!”
-Amy. J
“We were met by an incredible team upon arrival at Casa San Francesco. The staff were not only helpful but we felt like we had friends in the neighborhood. They got us settled in. Answered our questions. And then provided us unparalleled service with the extra tours we planned. Whether it was the walking tour of Cortona, the day trip to Florence, the wine tasting tour or the night out to eat in Cortona, the team and her English speaking locals made us feel like special friends they wanted to take care of.
And I have to give a special shout out to Ivan the chef. We did in in villa cooking class experience. It was one of the highlights our whole crew chats about the most when we reminisce. Making homemade pasta, Tiramisu, along with salads, appetizers and of course plenty of wine...we laughed and ate the night away.”
-Kurt J.