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.

You’ll savor a multi-course farm-to-table dinner at a beloved Cortonese eatery, expertly paired with Tuscan wine and prosecco. 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!

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.”