Trending: Villa Family Vacation Under the Tuscan Sun

One of the effects of Covid-19 is people’s inability to see family and friends. Couple that with the public’s inability to travel and we are now seeing a huge resurgence of family and friends group travel. This summer I was very busy planning family trips to Egypt, Turkey, and Europe, including my very own Cabrera family trip to Italy.

I took on my family as VIP clients and created a stay in Florence that included museum visits and a private room welcome dinner by the Savoy Hotel’s chef at Irene Ristorante, followed by a week-long stay in a villa near Bramasole Cortona with our own private chef, Valentina, who cooked for 14 of us every morning and evening. Breakfasts were hearty and dinner always started with homemade appetizers followed by an extravaganza of local Italian specialties. There was always fish and meat to accommodate our pescatarians and meat eaters.

The ability to enjoy a vacation in a villa without having to worry about cooking for a group this size was liberating. The 15th century farmhouse turned 8 bedroom 8 bathroom luxury villa with pool, and adjacent fig tree orchard, and vineyards overlooking a lush green mature tree valley near Cortona, was just magical. We traveled in September so the days were warm and the evenings crisp. Perfect fashion weather as a stylist friend of mine likes to say about days like this.

During the day I arranged a marvelous luxury bus with driver to take us around Tuscany along with our charming and knowledgable guide Francesca, who immediately simply became part of our family. She helped us explore medieval and renaissance “montes”, like Montepulciano, Montalcino, Citta della Pieve, Pienza, Cortona and Perugia. I like to call them montes because they are all hilltop towns that are just idyllic. We tasted saffron-infused delicacies and sangria in one monte; wood oven baked pizza near Lake Trasimeno; shopped for ceramics in another monte; tasted extra virgin olive oil at a farm; private wine tastings everywhere we went; lunches cooked by a grandmother in one hamlet; and everywhere there were hilltop views right out of a Tuscan landscape oil painting.

But it was not all eating, wine tastings, and charming village exploration. We even had time to jump in the pool a few days and, you guessed it, eat and wine taste some more. Yes there were heated debates, some tears, a lot of appreciation and many kisses. It was just a beautiful two weeks on our family trip. I can’t wait to recreate this experience for another group of family and friends so they can experience a magical time under the Tuscan sun. Email me at or call 1.773.772.9666.

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.