Under the Tuscan Sun for 8

an Experience-Based Package

Package Includes:

7-night stay for 8 people at the breathtaking Casa San Marco, a historic 4-bedroom, 2-bathroom artist’s home in upper Cortona with a broad terrace and sweeping views of the valley.
One multi-course, in-home chef dinner for 8 paired with a selection of regional wines
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

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 7 nights in a beautifully-curated artist’s home, Casa San Marco, a 4-bedroom, 2-bathroom home for 8 people, with a terrace and a breathtaking view that overlooks the Church of San Francesco, the Val di Chiana Valley, and Lake Trasimeno. 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.

Immerse yourself in a quintessential tasting room steps away from Piazza Della Repubblica in central Cortona. At this charming cantina, you will delight in legendary Tuscan wines and 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 tasting with a special gift reserved for our guests to enjoy in your Cortona home.

You’ll luxuriate in having an authentic Tuscan multi-course dinner prepared for you at Casa San Marco by one of our talented Cortonese chefs. Your meal 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 aperitivo drink of prosecco followed by an excellent local wine will be provided. Special dietary needs can be accommodated if necessary.

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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What our Guests are Saying

“We loved our stay at Casa San Marcos in Cortina! The villa was so beautiful which matches the views of the Tuscan region.
The team led by Frederica and Gloria were amazing hosts that added to our wonderful stay! We will not forget this trip and would defiantly return in the future!”
-Mandy B.
“We had a wonderful time here. The villa is incredible, and Stacey is a wonderful host.”
-Lisa H.
“We had a wonderful time in Cortona at Casa San Marco and visiting Italy. The villa was amazing and the support staff that assisted us while in Cortona was outstanding. Always there to help, they made the trip even more enjoyable.
Thanks for providing us a great place to stay with wonderful lasting memories!”
-Lee M.
“I knew that Cortona was going to be beautiful, and the pictures of Casa San Marco that we saw before the trip were amazing. It was even more gorgeous in person!! They thought of EVERYTHING we might need during our stay. The kitchen was so fun, and where we hung out a lot of the time. We even had a cooking class which will be something I’ll treasure forever! The hosts made sure we had everything we needed, and were so nice and sweet! The decor….wow!!! It was a great mix of old Italy with all of the amenities you would need today! We all slept like babies In our comfy beds and rooms. The town of Cortona was so relaxing, and easy to take day trips to Tuscany for wine tasting or Siena which was lovely also! I got to be pretty good at waking up the hills also ha! I hope you love it as much as we all did! Six of us stayed, and we had so much room”
-Tara S.
“Casa San Marco in Cortona-high on the hill overlooking the entire Tuscan Valley and Lake Trasimieno is one of the most remarkable places to stay in Italy. Close to Assisi, Florence and many other of Tuscany's wine towns and attractions, it is perfectly located and perfectly equipped for a vacation stay.
The home is so lovingly cared for and beautifully decorated, the kitchen has everything you need to cook magnificent italian meals with local fresh pasta, produce, artisanal meats and wine.
Sojourn Ventures takes great care of their clients from the moment of reservation to the end of the stay and can connect guests to cooking classes, tours and special experiences throughout the region. We have stayed twice and loved it. We will be back.”
-Julia Z.
“You asked about our stay at Casa San Marco, I don’t have the vocabulary to really express how awesome and lovely it was. They decor was spot on for what my wife would like to our house here. The view from the balcony is second to none, and I spent almost all of my time there. A glass of wine, a book (though the view kept distracting me) and I was happy and content. So we had three kids there and as kids are they tend to play loud, my 10 year old daughter felt bad for the lady that lived under us, so she wrote here a letter. We used google translate to write her a letter to apologize for any loud thumps that might occur and asked her some questions about her and her life here. Not sure how accurate google translate did, but I think the spirit of the letter came across. The lady was so sweet, she made her a fig tart that was so delicious that I had to fend off the kids so my wife could get a piece :) She was the sweetest person in the world and truly represents Cortona.”
-James S.
“This house is one of they most beautiful authentic homes I have stayed in in Italy. The hill town of Cortona is full of shops, great museums, art galleries, great restaurants, wine shops, beautiful churches, and a Medici fort. The bds are comfortable with crisp white sheets.Each morning the bells of the famous church San Francisco chimed sending the nesting birds a flight. From the bedroom balcony you can overlook the lush valley of rolling hills and the mountains and dormant volcano in the distant. Wee we cooked many meals in the well equipped kitchen and raised a glass to our fortunate luck at finding such a wonderful place to stay. Every shop is walkable. No parking but no need for one. Enzo was always available to take us on far reaching adventures or just to the train station for day trips to Florence or Abrezzo. I still dream of this perfect spot. One warning, you must be able to climb one flight of stairs and walk up beautiful cobbled roads and paths.”
-Ronald N.
“We loved every minute in this gorgeous home! When we were too tired from walking the hills, we enjoyed sitting on the balcony and listening to the sounds of the neighborhood and seeing the amazing sunsets.”
- Kathryn D.
“Words cannot begin to describe how wonderful our stay has been at Casa San Marco! We came together with friends and family and enjoyed 7 beautiful days in Cortona. This home and this village are absolutely charming. From booking our stay to arriving in Cortona, all the way until our very last night here, everyone has gone above and beyond to make us feel at home. What a fabulous team of people working to help us create beautiful, cherished memories for years to come!”
-Greg & Stacie H.
“Really an adventure of a lifetime! There is something timeless about this place that makes someone feel linked to people long ago. Maybe the stones tell stories for the world to hear. In any regard, it is a love story. Thank you for sharing your home and love story with us.”
-Bambi A.
“Thank you for opening up your beautiful home to us. We loved our stay here and had such a great time exploring Cortona and the surrounding area!”
- The Mello Family
“Thank you so very much for allowing us this respite in Casa San Marco! We shopped, we ate, we laughed and loved. The grand finale was an evening of being taught how to cook an Italian meal by Ivan. Molto Bene! Just absolutely amazing in every way. This home is absolutely beautiful and we are so grateful to have had the experience in Cortona!”
-Jan and Michael T