Italy summer vacation part one, Umbria

With 2026 beginning, it is a good time to reflect on a few of our trips last year. My wife noticed that for vacation entries I tend to cram all parts of a trip into a single post. This is overwhelming and occasionally I avoid writing about our travels entirely. From now on I will be breaking up our longer trips into multiple parts, which will hopefully lead to more frequent and timely posts.

We began our vacation by landing in Rome after an unpleasant experience at the London Heathrow airport where we missed our connecting flight. Thankfully, the rental company held the car for us and we were soon on our way to Perugia which was a little over two hours away. Perugia is the capital city of Umbria and served as our base. We stayed just a bit north of Perugia, in the hills near San Marino, and had a rental property with a private pool and gorgeous views of Perugia in the distance. At the property we met up with my sister and her family who had some delicious pizza waiting for as soon as we arrived to start out the vacation the right way.

Our first excursion was an evening trip to the medieval walled town of Spello. Spello’s old town, located on a hill-top, is exceptionally charming with beautiful cobble stone street and narrow alleyways. Follow the main street up to the hill-top and you will be rewarded with stunning views of the countryside. There are plenty of cozy restaurants to choose from and for dinner we ate at La Cantina di Spello. Very lovely décor wise, but the entrées that we chose were average at best. What soured our experience more was the service, which was exceptionally slow. Our last course came so late that all we wanted to do is pay the bill and get going.

To make up for last night's culinary disappointment, we went on to explore some agritourism on a farm located between the towns of Bevagna and Montefalco. The food was good and along with some nicely prepared side dishes, we got to taste a certified Chianina cattle, expertly prepared by our host. It looked great on the plate and was pretty good, but all things considered I still prefer a good old Texas steak. Afterwards we visited the town of Montefalco which is just a few minutes away. It was nice, with some great views of the country side but I would not consider it a must see. At this point we were tired, but decided to stop in Bevagna as it was on our way back. We did not expect much but were surprised beyond expectations as we stumbled into the Mercato delle Gaitte - an annual medieval festival which transforms the town completely and takes it back to the thirteenth century. Hundreds of people were dressed in extraordinary outfits and stayed completely in character - and they do it for days. There were women washing clothes in the river, a paper mill with gorgeous manuscripts, and a painters shop - just to mention a few. Street merchants, lined up along the narrow alleyways by the main plaza, were selling all sorts of things, as if crafted by artisans many years ago. If you can schedule you vacation to coincide with this festival it would be shame to not attend.

In between all of these travels some tennis was required. Thankfully Perugia has a fantastic tennis facility, namely the Tennis Club Perugia. This club hosts an ATP Challenger 125 tournament, Internazionali di Tennis Città di Perugia, and several other tournaments. It is conveniently located near the city center and has nice views of old Perugia. As is the case for many tennis clubs in Europe, it had a very nice clubhouse with a coffee bar, pastries, and various aperitives for after tennis relaxation – American tennis clubs could learn a thing or two here. I was lucky enough to get in touch with Federico Rosi, who is a teaching pro at the club, and managed to get us all on the schedule for a few tennis lessons and drills – playing on clay is always a lot of fun. Another member of the club insisted on sharing some of the club history with us, took us around the grounds, and even procured some branded gear. With Jannik Sinner at the top of the ATP rankings and nine Italian men in the top 100, tennis has become a very popular sport in Italy recently.

After the tennis helped us shed a few pounds, it was time for another excursion, this time to Assisi. Assisi is a UNESCO world heritage site and is perched on a picturesque hilltop. Thankfully there is an escalator from the parking area at the bottom of the hill to the town center. Assisi is a fairly popular destination with pilgrimages and tourists alike. It is the birthplace of Saint Francis of Assisi, the founder of the Franciscan Order, and also Saint Clare of Assis who founded the Poor Clares. The town is lovely and once again there are many spots in which one could dwell for hours. It is a little busier than some of the places we visited, but by no means crowded. The Basilica of San Francesco is stunning with multiple levels, each a separate church, and a crypt underneath it all. This Basilica and Assisi were one of the highlights of our trip.

For chocolate lovers, the Perugia Chocolate Museum is worth a visit. It is the birthplace of the famous Baci chocolate kisses. You get a nice tour with historical posters, advertising, and a walk above the factory floor. Of course, you get to taste all the different Baci flavors, and you can pick up a lot more at the gift shop. On a side-note, in the same factory they produce two thirds of all KitKats for Europe.

Next on out itinerary was the town of Gubbio. We began our trip with a bite to eat at La Cresciamia. It proved a lovely place to start. The ambience is very chill with a long bar on the side and some seating towards the back. But the real gem is the basement, where long tables and benches line the historic stone wall. Be careful descending as the stairs are narrow and steep. The menu was a little different than we have gotten used to in Italy, with no pasta or pizza dished. Instead, the menu was full of sandwiches featuring many local ingredients all served on some of the best bread on our vacation. The sandwiches are complemented with a variety of charcuterie boards. One word of caution, the sandwiches are large so be measured when ordering. Bellies full, we took a small detour visiting the Roman theater nearby before walking up towards the historic town center. The street is steep and long - be prepared for a fairly good workout. Once you make it to the top you will have some sweeping views of the country side and if you have any energy left be sure to visit the Palazzo dei Consoloi which has some really nice artifacts dating back to prehistoric times. The museum is nicely laid out, was not crowded and had air conditioning which we really needed at this point. As a bonus, at the very top of the Museum is a tower with a stunning terrace for unobstructed views spanning for miles.

Before heading towards Tuscany to meet up with our friends, we visited a couple restaurants which deserve a mention - the first of which was Taverna Del’Orso. The restaurant is located in a very simple yet picturesque farmland setting. Don’t let that deceive you though, as the restaurant is lovely and the food was fantastic. To sit inside you may need to make reservation, but the outside where we sat was very pleasant. Once again be sure to not over order. The pasta dished were gigantic even by American standards. The other mention goes to Osteria Del Donca, where we had our best meal experience in Umbria. It is a tiny spot near Ponte Pattoli on the outskirts of Perugia and very easy to miss when driving by. It has an indoor and outdoor area, and also a small garden area when our kids could play while we enjoyed dinner. A most unique item was a cream covered egg with pistachios which was simply delicious. The carpaccio was very good, and the pasta and boar dishes were excellent. It is quirky place where the outdoor does not match the indoor, and they even have a video game machine near the inside bar - much to the delight of our children. The service was excellent and the ambience was nice and relaxing – no crowds, reasonable prices, and extremely good food. It was a perfect way to close out our time in Umbria.