Umbria like a local: Private Wine Tasting & Dining Experience

Wonderful experience. Monia did a fantastic job, I felt part of her extended family during my visit there. All activities were nicely curated to my interests. I enjoyed every moment of my time there. The food and the wine were the cherry on top!

We went to Umbria as a family last summer and had the best vacation. We stayed in Passignano, and Monia knew all the best spots and was an amazing guide (and friend) throughout our visit. I went with my mother and my grandparents and she made things interesting for each and every one of us. Highly recommend visiting with her.

WhenInUmbria, and specifically Monia, is a treasure for travelers who seek rich, immersive experiences and authentic connections in and around Umbria. The food was delectable, the wines delicious, and the experience among the most positive and memorable of all my travels. Highly recommend!

I visited Umbria with Monia in for a week in both July of 2025 and June of 2023. The experience was amazing to say the least. Monia is so helpful when you first arrive, getting you to your AirBnB and giving you the lay of the land. I got to go on a tour of the historic castle, she gave us so many recommendations for places to eat, and other villages near by to check out. If you want to experience Italy the way the locals do, you have to do it with Monia. She seems to know everyone in town, and gives you a real taste of la dolce vita. Hands down the bet dinner of my life was one Monia took us to in the hills of Umbria. It was this amazing restaurant over looking the countryside. The food was incredible, and we stayed into the wee hours of the night drinking limoncello with the owner of the restaurant because Monia was close with him. She also took us to this picnic in the countryside with tons of food vendors where we sat on the rolling hills and watched the most beautiful sunset. She also introduced us to the Umbria Jazz festival in Perugia (a quick 20 minute train ride away) where I saw jazz icon Herbie Hancock perform. I can not emphasize enough how amazing this experience was; there is no better way to see Italy.

+4

We stayed in a cute house the town of Passignano and we had a great itinerary planned for us, welcomed us with hospitality

I can’t recommend WhenInUmbria enough! From the moment we arrived, everything felt curated just for us — no crowds, no tourist traps, just pure Umbria. Our private guide made us feel like we were exploring with a friend who actually knows the hidden gems. We wandered through charming medieval towns, met local artisans, and tasted wines at family-run wineries that you’d never find on your own. The pace was perfect: leisurely strolls through cobbled streets, delicious lunches in authentic trattorias, and sunset aperitifs overlooking Lake Trasimeno that felt straight out of a movie. What really stood out was the personal touch. Every stop was thoughtfully planned, from the olive groves to the hidden piazzas, and our guide shared stories and insider tips that made the region come alive. This wasn’t just a tour — it was a full-on experience of Umbrian life. If you want to experience Umbria like a local — with wine, food, culture, and heart — book with WhenInUmbria. Truly unforgettable!

I am so glad I connected with Monia at When In Umbria. She asked the right questions to understand what I wanted to experience while visiting Italy, and directed me to several sights and events that I would never have found, including a sunset "picnico" at a winery (complete with wine, music, and a porchetta truck!) and a private dining experience at a high end villa perched uptop the hills of Passignano with outstanding views of Lake Trasimeno. No wonder the Hollywood elite are purchasing properties there. I can't wait to visit again!