A few years ago I was inspired by a friend to create a list of 50 things I wanted to do before turning fifty years old, my 50 x 50. On that list was a trip to Italy with my dad. Not only was I lucky enough to experience that recently, but my brother and aunt and 20 other family members came along for the ride!

We found a villa in a small town in Tuscany called Cetona that – believe it or not – accommodated all 28 of us. Throughout our two week stay at the villa our family often broke off in to smaller groups to explore different areas. Because it was the first time in Italy for more than half the group, they wanted to see many of the places that my immediate family had already explored, and rightly so. With the exception of Florence, my immediate family focused on visiting towns that were new and unexplored to us.

If there is one thing I could improve upon, it’s travel planning. Picking cities and apartments (or villas) that are a good fit for my family? I’ve got that down. But that’s basically where my travel planning ends. Partially because I prefer not to travel like a “tourist” and partially because the task of securing accommodations tends to tire me out, I never really and truly research an area prior to arrival. So it’s no surprise that I did not have a daily itinerary planned out. Somehow, someway, it always works out.

One of our favorite things to do is to talk with the locals and solicit their feedback about where they think we should explore. We met a local wine maker from Cortona and after spending an evening drinking his wine and enjoying a wonderful meal with him, we asked for his recommendation. Without hesitation, he suggested Orvieto.

There were so many fabulous things about this little hilltop town that captured our hearts. To begin with, many of the cobblestone streets are restricted to pedestrians only so it was nice to allow my kids to run around without fear of a crazy Italian driver running them down. And that cathedral! Though they would not allow photography inside, you’ll need to trust me when I tell you that the Orvieto Cathedral is one of the most beautiful churches I’ve seen. And throughout Italy alone, I’ve seen many.

Though our children had a fabulous time simply running around, enjoying panini and gelato – their favorite things about Orvieto are:

Art
I love that my kids noticed that much of the art they saw on the streets and in the little shops in Orvieto was different from what they’d been seeing thus far on our journey. Almost everywhere we turned we saw something else that caught our attention. The art was whimsical or modern versus traditional or ancient, and they loved it!

Underground Caves
While Orvieto above ground is completely charming, it’s what underground that captured the attention of my kids and offered them some much-needed time out of the summer heat. The 45-minute tour showcased a few of the more than 1200 Etruscan caves, tunnels, passageways and rooms that have seen a variety of uses over the past 2500 years including refrigeration, bomb shelters and wells. Many of the 440 caves are still in use today by private owners as basements and wine cellars. My kids were fascinated by, in particular, the many rectangular shaped “holes” dug out of the volcanic tufa.  We were told that these little holes were actually used to raise pigeons for food, and kept the locals well-fed for centuries.

Our tour was conducted in English (though they also accommodate Spanish, German, French and Russian) and is free for children five years old and under. Our guide was knowledgeable, interesting, and engaged with the kids – which was greatly appreciated. The tours take place daily with the exception of February, in which case they are weekends only.

Orvieto’s Flags & Banners
My son, in particular, was obsessed with the great number of flags and banners we saw on our walk through Orvieto. They are bright and colorful and hang all over town. We learned that each year on the 9th weekend following Easter Orvieto celebrates Corpus Domini, a religious holiday established by Pope Urban IV as the result of a miracle experienced by a priest in 1263.  That priest, Peter of Prague, had evidently been doubting the ability of the bread and wine to transform in to the body and blood of Christ however, one day while at mass he witnessed a miracle: blood coming out of the bread during communion.  This miracle was communicated the the Pope, who ultimately declared the religious holiday as a result. The celebration is extremely important to Orvieto as the pope was living there at the time the holiday was declared. The festivities include a spectacular parade full of color and – as you might have guessed – showcases the beautiful flags.

Our family greatly enjoyed our day in Orvieto and would highly recommend the visit to not only families, but absolutely everyone!