
I fell behind on documenting some very exciting travels in 2019, but that won’t stop me from reminiscing here and now on the Gypsy Kitty Diaries 🙂
For two weeks last summer – just about one year ago, to be exact – Chuck and I explored Italy with his darling family.
Now, all countries are too diverse and amazing to squeeze into one trip, but Italy was especially frustrating in terms of the limitations we had to impose on ourselves. Still, I like to think we did quite well. Chuck and I started out on our own in Como before driving to meet family in Tuscany and then wrapping up in Rome. Check out our highlights!
I will spare you the details of the rental car debacle upon our arrival in Milan, but trust that it was quite the adventure getting from MXP to our lakeside hotel in Como that evening. We stayed at the pretty Palace Hotel Como, which – I’ll be honest – wasn’t quite as luxe as anticipated (for a splurge). That said, it was a nice little spot. It just could have used some updates!

Como itself was clearly the touristy hub of the region, but we were very hungry and hurried to the nearest eatery, where I ate a sub-par, depressingly American-style cheese pizza (which falsely identified itself as a “Margherita pizza.”) The quest for a truly great pizza became central to my time in Italy, which was particularly frustrating considering I am mostly vegan and prefer to avoid so much cheese!
Anyway, day two in Como was better. We took the ferry to Bellagio, and had the most lovely time strolling the village. It was warm, but not unbearably hot, and the colors and atmosphere were simply luminous! I could have wandered those alleys and explored those nooks for days.
We dined at the fabulous La Colombetta in Como, an alleged favorite of George and Amal Clooney, and I can say with conviction it was the best meal I had in Italy. It was a truly romantic evening. Great food, wine, and plenty of flouncing around in a little white dress that was far too short and much too revealing of the décolletage region. #SorryNotSorry, as the kids say 🙂
But then it was time to turn to a different type of fun. Chuck and I hopped in our plucky rental car and ventured south to the lush hill towns of Tuscany. At a charity auction in DC a couple of years prior, Chuck’s parents had bid on a villa in the medieval town of Cortona (of Under the Tuscan Sun fame!) They were so kind as to include the whole family in this novel adventure, so the Jedlickas Senior + Jedlickas Junior joined forces for seven days at the Casa Ombretta.
We used the villa as our home base while exploring other areas of Tuscany. We experienced wine tasting and pasta-rolling in Montepulciano, Franciscan cathedrals in Assisi, and art + gelato in Florence. I loved Assisi the most, but my favorite personal experience was escaping the heat to read a novel under the shade of the olive tree at Casa Ombretta 🙂
One day in the middle of Tuscan week, Chuck’s parents, sister, and aunt wanted to do a day trip to Rome. We had plans to visit Rome later on our agenda, so Chuck and I opted to day-trip to Cinque Terre instead, with Chuck’s brother and his girlfriend. We roused early and drove nearly three hours to experience salty air and vitamin sea – and I have zero regrets (never mind that Chuck did all the driving!) Despite the fact that the coast gave little reprieve from the oppressive heat that plagued us the entire trip, I couldn’t get over Cinque Terre’s vibrant beauty.
As our week in Tuscany with the family came to a close, it was time to gear up for Roma. One family member did tag along – our lovable brother Jake – and the three of us shared a flat mere blocks from the Colosseum, courtesy of AirBnB. Despite lingering exhaustion from the first 10 days of our journey in the epic heat wave, this ancient city was exhilarating. I found myself enjoying it even more than Florence. We toured the Vatican, dined on the Tiber, browsed ancient relics, and tossed a coin into the ornate Trevi Fountain!
I even found the perfect pizza – finally!

I still think I have a preference for France. The food and people didn’t live up to the hype in Italy, but in all fairness, a large American group hitting the most touristy spots is less likely to find those more intimate experiences. But all in all, Italy was one for the books, and that history can’t be beat! I’d love to get back some day to experience Venice and the Amalfi Coast! And perhaps a jaunt to Capri 🙂
Until next time, Italia!
