Seeing Italy for the First Time

Italy is as picturesque as advertised, but getting to everything worth seeing is an adventure.

H aving spent many years vacationing close to home when the kids were younger, my wife and I finally began seeing Europe the past few summers. I wrote here of my first trip to Britain in 2023 and to France (my first time on the European continent) in 2025. Our youngest is studying in Rome this fall, so this made a good excuse to add Italy to the list. With our three kids (ages 20-29) and one significant other, we spent twelve days seeing Rome, the Vatican, Castel Gandolfo, Assisi, Florence, Pompeii, and Naples.

It appears that we were there at the same time that Brian Allen was visiting da Vinci’s The Last Supper in Milan. In one sense, this is a good time for Americans to see Italy, with the dollar very strong against the euro. On the other hand, many Italian businesses aren’t open in August. We were stuck buying snacks at a mini-mart for “dinner” when we arrived in Naples after dark because the only pizza place within walking distance had a sign that it was closed for a month. Worse, Italy was possibly the hottest place I have ever been, with the necessity to drink water continuously all day to stay on your feet seeing sights and to shower and change clothes as many times a day as possible. I think you could have forged the One Ring by setting it on the sidewalk for ten minutes.

It is a challenge to get one’s hands around Italy even with two weeks in the country. Seeing London or Paris with just a few day trips outside the capital can deliver a sense of having seen the really essential parts of England and France, notwithstanding the many attractions and points of interest in smaller cities and the countryside. But the nearly 1,400-year interval between the fall of the Roman Empire in the West in 476 a.d. and the reunification of Italy in 1860 ensured that neither history nor culture would be consolidated in the capital. The independent republics and centers of art and faith ended up distributing landmarks up and down the Italian peninsula. Then again, there’s so much to take in of ancient, early Christian, medieval, and Renaissance Italy that there’s little time left for modern Italy.

Indeed, at such a long distance from the Pax Romana of Augustus, when all roads led to Rome, it was a struggle of the 19th century to rebuild the idea of Italy as a single nation (with a big assist from Napoleon’s short-lived Italian kingdom). Metternich famously sneered that Italy was only a “geographical expression.” By some estimates, between 2.5 and 10 percent of the population of the united Italy in 1861 spoke the Italian language, with most speaking separate regional dialects. The Italian politician Massimo d’Azeglio then quipped, “We have made Italy. Now we must make Italians.”

Italy today is not a place of great cities. Rome houses about 2.7 million people, around the size of Chicago, although its metro area of 4.2 million is closer in size to those of Seattle or Detroit. Milan is the only other Italian city of a million, although Naples is not far off. To cover Italy adequately, one must journey through the picturesque countryside of rolling hills, mountains, forests, and farmland.

In planning our trip, we initially tried to travel by trains and buses, but when we were wearying of Uber bills, train schedules, and dilatory buses halfway through the trip, we discovered too late that an international driver’s license is needed to rent a car. (While Uber rides are comparatively cheap by American standards, they still add up in a hurry if you need to use them more than occasionally). That imposed choices: We knew all along that we couldn’t make it far enough north to see Venice or Milan, or south to the Amalfi Coast or Sicily, and we had to abandon original plans to see the Leaning Tower of Pisa and (much to my wife’s distress) the Veil of Manoppello.

If you intend to travel far from Rome or to smaller towns such as Assisi, I would recommend either planning in advance to drive or building in a lot of travel time. On our return train trip from Naples, a malfunctioning ticket machine left us having to buy pricey first-class tickets in order to get back to Rome in time for our flight home (upside: airline-style cart service). On our trip to Assisi, we weren’t able to get the door to open at our stop and had to get a car back from the next town. Then again, in Castel Gandolfo, we would never have been able to locate the apartment we rented without the assistance of a cab driver who made a long phone call for us in Italian rather than just abandon us on the street. This was one of several times that we needed to rely upon the kindness of Italian strangers, whether or not they spoke English.

My wife, being the theologian in the family, ensured that we would see a very Catholic agenda of basilicas, the Vatican, a papal audience, the Mass of the Assumption said by the pope at Castel Gandolfo, and a profusion of religious art, tombs, catacombs, and other sacred sites. It fell to me to insist that we not miss pagan Rome: the Colosseum, Pompeii, and the Pantheon. But even there, the Colosseum features a large cross memorializing the many Christians martyred there, and the Pantheon has been a church for centuries.

In retrospect, Naples — which we chose mainly as a place to spend the night after seeing Pompeii — was not worth the trip. Pompeii is doable as a day trip from Rome, or one can stay in the town. Seeing Naples was more like seeing the Bronx. Not what you cross the ocean for.

The biggest excitement of the trip was seeing Pope Leo XIV up close in person at Castel Gandolfo, which is a picturesque medieval town overlooking a gorgeous lake. The Holy Father really looks and carries himself like a pope, and just exudes a sense of joy and peace that is palpable as well as papal. Castel Gandolfo, a town of some 9,000 people, is built around a small, enclosed town square. While security was tight entering the square, it’s a far more intimate setting than the vast throng of St. Peter’s. You can see even from public photos how small the square is. The crowd was waving “Benvenuto Papa Leone” flags to match a huge banner near the church, and given that the town’s economy took a blow from Pope Francis not using it as a summer residence, the warmth of the outpouring for Leo XIV was clearly not only spiritual in nature. My wife was able to get far enough up in the crowd to shake his hand, which was the highlight of the trip for her. Walk-up visitors can’t just get into the church for Mass, but it was broadcast on a big screen for those left outdoors, and Communion consecrated by the Holy Father was distributed.

It’s unlike anything in America to be in a town where people still live in medieval buildings along medieval streets. This was especially true of Assisi, a hilltop town of 27,000, but also of the older parts of Florence around the Cathedral of Santa Maria del Fiore (better known as the Duomo). We went to Assisi in large part to see the burial places and relics of St. Francis and St. Clare, but the town itself is wonderfully transported from everyday American life even if you’re not there for the religious experience. More harrowing was encountering cars driving up and down 45-degree angles on streets only wide enough for a car and half a pedestrian.

The highlight of all the sites, to me, was the Pantheon. It’s the one Roman monument that is not a ruin: you can experience the building much as the ancients did, and its dome is spectacular. It’s also an eclectic burial place, with the tombs of Raphael and of Victor Emmanuel II, honored grandly with fresh flowers as the “Padre Della Patria” for being the first king of the reunited Italy (although he kept the “II” as the second such king of Sardinia). We saw a great many tombs, including the altar of Julius Caesar in the Forum near the Colosseum, the burial places of many popes in St. Peter’s, including John Paul II, Benedict XVI, and Paul VI; the tomb of St. Francis in his basilica in Assisi; the tomb of Pope Francis in the Cathedral of St. Mary Major; the tomb of St. Sebastian at the Basilica of Saint Sebastian Outside the Walls, atop the catacombs of St. Sebastian. We paid for a number of guided tours, which were worth the price, as our tour guides at the Vatican, the Colosseum, and Pompeii were very knowledgeable; the latter two were archaeologists. (Sadly, we toured the Colosseum during the week, so we couldn’t get into the Roman Senate, which is only open on weekends).

Florence is full of attractions, including museums honoring Dante, da Vinci, and Galileo. The da Vinci museum has an impressive collection of full-scale models of his inventions. The Duomo is spectacular, and doesn’t look like anything else. I climbed the 14th-century bell tower, whose 414 steps rise multiple levels and are not for the faint of heart, especially in 98-degree weather.

The amount of artwork to be seen, especially church artwork, is just staggering, with many churches just so chock full of art that it’s impossible to take it all in. Some of these, like Bernini’s sculpture of St. Theresa at St. Mary of Victory and Michelangelo’s incomparable Moses at St. Peter in Chains, are at churches you might easily miss if you don’t search them out. Michelangelo was, of course, the creator of the greatest of these, whether they be the Sistine Chapel or the Pieta in St. Peter’s. But the pinnacle is the David in Florence, which is every bit as impressive in person as you may have been led to believe.

As an experience, seeing the Mona Lisa at the Louvre is just not in the same class as seeing the David. What makes the Mona Lisa great art is its subtlety, but it’s a small painting in an overcrowded room where the best you can do is manage a selfie over the throng. There’s no way to actually appreciate the painting as an artwork. But even for a philistine such as myself, you need know almost nothing of art to be staggered by the skill and beauty of the David, and it is presented in a large, airy, unhurried hall in which you can linger as long as you like and walk around to see it from every direction. The hall itself houses multiple other Michelangelo sculptures that would be the centerpiece of most any other collection, including a rougher and more emotional Pieta.

The last of the great sights was Pompeii, which owes its unusually preserved ancient layout as a town to the fact that the volcanic ash that buried it wasn’t excavated until the 19th century. It is worth the trip not only for its “frozen bodies” and frescoes, but also its ancient amphitheater and the mosaics and even bar counters that are startlingly intact.

There of course is also the food, wine, and setting in addition to sightseeing. In stark contrast to England in particular, the restaurants are open well into the late hours. I confess to being disappointed at the Italian habit of serving red wine at room temperature, especially when the room is at is the temperature of the surface of the sun.

English was more widely spoken in Rome and even in the smaller cities and towns than I had expected, and there was one big difference from France: instead of signs and announcements in multiple languages, anything in public that wasn’t only in Italian was in Italian and English — but no other languages. (This was less true in the Vatican, or in some churches where we saw Italian, English, and Polish). Rome is a cosmopolitan city, and the presence of the Vatican in its midst only makes it more international. But outside of Rome, most everyone we encountered was clearly native Italian, even in this age of mass migrations.

Travel is always an adventure, especially abroad, and the sheer mass of things to see and how far apart they are present a challenge in truly seeing Italy — that is, slowing down enough to take in its charms alongside its ruins, its artworks, and its astonishing vistas.