Italy surprised me. Places I thought would be okay turned out to be my favorites, and places to which I most looked forward got on my nerves at times. I'll break it down by city:
Milan: Loved it as much as Rome, making it tied for my favorite city in Italy. It's glamorous, it's full of things to do, and there's no shortage of great Italian coffee and gelato.
Rimini: Would someone visit Rimini if they were not planning to visit San Marino? Probably not. We really enjoyed it, though, and I do recommend seeing both the waterfront area and the historic downtown (the latter being my favorite).
Parma: It's a beautiful small city, with an awesome museum (Pallazo della Pilotta).
Rome: Loved it. It felt like London to us in the sense that there are endless neighborhoods to explore, things to do, and places to eat. Somehow it felt less touristy than Florence. I'm sure there were more actual tourists in Rome, but they were all in line for the Colosseum and St. Peter's Basilica, so it wasn't hard to find less crowded areas of the city in which to relax (if you've seen those lines, you know). It was more walkable than I thought it would be, but there was still public transit as a backup.
Florence: While the city itself is gorgeous and iconically Italian, the density of the crowds (and the difficulty in navigating around them on the narrow sidewalks and streets) got to me. The crowds, by the way, were tourists, tour groups, and people selling selfie sticks.
Bologna: Our gondolier in Venice asked us why we had gone to Bologna. My knee-jerk response to him was, "Why not?" (Another one of my favorite and equally-valid responses is, "Because we haven't been.") Having been, I can say there are several reasons to visit Bologna. The food is the first reason. The restaurants are on-par with the other major cities in Italy with a much lower price tag. Another quality is the quiet, calmness of it. It was a nice break from everything to be able to wander down pin-drop quiet streets. What stood out most to me, though, was the number of bookstores and libraries. Bologna is a city of books. Even their Eataly is a bookstore combined with the traditional Eataly grocery/restaurant sections. A city with that many bookstores and libraries has to be great.
Venice: It's so remarkably beautiful and unique, that you have to love it. Nothing more to be said.
In 2015, after flying to Istanbul and Malta, we took a one-way flight on Air Malta to Rome. From there, we took trains to Florence, Bologna, and Venice. Do not underestimate the importance of booking your train tickets as soon as they become available. We got fantastic deals on every leg of the journey by booking months in advance directly from Trenitalia. In 2025, we flew on SAS via Copenhagen.
I was trying to record the music that this three-man band was playing. This is something I frequently try to do without being noticed. This time, however, I was noticed, and his face still makes me laugh.
Malta is a tiny island nation just hanging out in the Mediterranean Sea, somewhere between Sicily and Tunisia. It's part of the European continent, but tectonically-speaking it's Africa. To me, though, Malta was more like Jordan than anything else. From the Arabic-influenced Maltese language to the sandstone-colored buildings to the landscape of its countryside, we were reminded of Jordan at every turn. Malta does, however, have its own very distinct cultural identity. If it is part of Europe, it's not like anything else in Europe we've ever experienced. It's a blend of the regions that surround it, with a little British peppered in.
Malta was the inspiration for a trip, which also included Istanbul and Italy. There are no direct flights to Malta, so we flew on Turkish Airlines so that we could have bookends in Istanbul. From there, we flew on Turkish to Malta. After our time in Malta, we took a one-way flight on Air Malta to Rome, then trains throughout Italy up to Venice, and back to Istanbul on Turkish. Air Malta was fine, but the legroom was really tight. In terms of getting around Malta, they do have a good bus network, but it can take a really long time. Some of them choose to run the air conditioning; others do not. It's less than 2 Euros for a day pass, though, and the buses go to most parts of the country.
We saw a picture of San Marino once--a striking country that sits atop a mountain--and I thought I'd like to go there. That's how we planned this trip. (Quite the gamble, I know!) I also have a fascination with the European microstates. How has a country as tiny as San Marino managed to maintain its independence over the centuries? What cultural characteristics distinguish it from Italy? These are things I wondered.
Having concluded our visit, I can say with certainty that basing a trip on a cool picture is a very sound idea. First, I've never been to a historic downtown more disorienting than San Marino. It took me a few hours to get my bearings. The streets are winding and consist of inclines and declines only. It's no wonder we managed to walk 95 flights of stairs the day we arrived! There's also something remarkably unique about this historic city center being on top of a mountain. On a clear day, you can see all the way to the Adriatic Sea in the east and the Apennine Mountains in the west. On a cloudy day, you are walking inside of the clouds, which is, in a way, even more memorable than the beautiful views.
We flew into Milan via Copenhagen on SAS and took a high-speed train to Rimini. After staying the night there, we took an early morning bus to San Marino. It was easy. We arranged for the hotel to pick us up at the bus stop, which I recommend.
This is how quickly clouds moved in on top of San Marino. Luckily, we were able to finish up seeing the Second Tower, and duck into a cafe along the path to avoid the pouring rain and hail storm.