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  • Writer's pictureJillian Thomadsen

Italy Itinerary Highlights

Updated: Aug 16, 2023

Here are my itinerary highlights from a recent trip to Venice, Cinque Terre, Florence, Pisa, Capri, Amalfi, Pompeii and rome:


Venice: We toured the Jewish Ghetto, visited St. Marks, took a gondola ride, and then a real highlight was aimless travel on the water taxis. I say “aimless” because I cannot, for the life of me, read the water taxi map. I think one would need to speak fluent Italian plus have a degree in Advanced Nautical Navigation to figure out how to get from point A to point B. Luckily, we got the unlimited 48-hour travel card for 30 Euro and then just rode it around until we got tired and meandered back to our place. It was perfect.


Next was Cinque Terre: In addition to the hike between towns, we took the Cinque Terre train to Levanto and rented bikes, then rode on the converted 19th century railway track through tunnels to Framura. It was a flat 1-hour ride with amazing views and no crowds.


One point of note: Levanto shops and restaurants close for their midday “riposo”. We learned this the hard way when we showed up at 1pm expecting to find a bike shop and everything was closed. After wondering if we’d made a huge mistake and should just hoof it back on the Cinque Terre train, we stuck it out in this beautiful town and rented from one of the many bike shops when everything reopened at 3 or 4pm. (BTW Google is absolutely no help in the matter, and doesn’t account for the midday siesta when posting hours of operation.)


Florence: How could you not love Florence? To be bored in Florence would be to dislike ancient sculptures and paintings (some dating back to the Middle Ages), to be unmoved by stunning 13th century architecture, to cast a callous eye towards the famed Ponte Vecchio Bridge, to scoff at Renaissance masterpieces. And in case you haven’t guessed by now, I’m talking about my 12-year-old son, who viewed these magnificent historical artifacts as mere roadblocks in his quest for more screen time.


But I fell in love with Florence. In addition to the aforementioned highlights, there’s The Cathedral of Saint Mary of the Flower (aka the Duomo di Firenze) whose dome is an architectural and engineering marvel in its own right, as it was built without buttresses or scaffolding in the 1400s. We got tickets to climb the dome, and let me just say that I felt like conqueror by the time I finished scaling the 400+ steps in the midday Tuscan heat. While taking in the sight of all of Florence laid out before my feasting eyes and waiting the 20 minutes to catch my breath, some of my guilt about my daily repeated intake of gelato, Nutella and all-carbohydrate pasta-and-white-bread dinners melted away.



Pisa: You won’t be shocked to read that the highlight of our half-day in Pisa was climbing the Leaning Tower and also coming up with silly pictures of ourselves manipulating the tower in ways that didn’t include the hundreds of other people ALSO pretending to manipulate the tower for photos. Beholding the landscape, I was just as moved by the Leaning Tower as the scene of people frozen in their poses. We all looked like some horrifying combination of Twister and freeze-dance. I had to wonder, if aliens visited Pisa on any given day, what would they think of humankind? Our intelligence forewarned us that humans were smart, they would say to each other. But the real leader is this mysterious rectangular object that commands humans to freeze into ungainly poses every nanosecond and press a button.


Capri: Capri is a beautiful island off the Amalfi coast, which has dramatic panoramic views, remains of ancient villas, sea caves and grottos. The most famous of these is the Blue Grotto, which is a sea cave with some of the most luminescent blue water you will ever see. Unfortunately, this also makes it a popular destination, and wait times to get in can be extensive.


For Capri, we rented a private boat and I could see the pain in our captain’s eyes when we told him we wanted to go to The Blue Grotto. I used to live in NYC and exhibited the same anguished expression whenever out of town guests wanted to visit the Statue of Liberty. But our captain very kindly obliged and after warning us that the wait time could be 1 – 2 hours of pure motor-fuel scented misery, he piloted our boat to the Grotto, and voila, it wasn’t actually that busy. We got our 5 minutes inside the Grotto and then toured the rest of the island.


Also – and I know this is going to cause some controversy, but I have to say it – the best gelato of the entire trip that I had was in Capri. Unfortunately, I don’t remember the name of this place, so mystified was I by this marvelous, velvety substance melting on my taste buds. The best directions I can tell you are to take the Funicular up and go to the gelato place across from the statue of the naked woman. I’m totally serious.



Amalfi: Do not go here if you’re allergic to lemons, hate the smell of lemons, have an unspecified aversion to lemons or are triggered by lemons in any way. I had no idea about the lemon thing before we showed up. Our place was right above lemon orchards, and I started to get the hint while showering with lemon-shaped soap after enjoying lemon-balls while drinking limoncello. By the end of your time here, you’ll be dreaming of lemons. I even broke down on the last day and bought a lemon-patterned dress. Why? I have no idea.


As for dining highlights…if you don’t mind climbing A LOT, I highly recommend a cantaloupe-themed (ha! Totally kidding!) lemon-themed restaurant. I’m sorry I’m so useless with names but it’s basically up the big hill and keep climbing. Once you’re dripping with sweat and questioning your decision to listen to me, you’ve arrived! It has 2 patios and around 6 delicious menu items that are all made from lemons.



Pompeii: Most of the places we visited, we took small-group tours, but in Pompeii I booked a private tour that billed itself as “child friendly”, since my sweet twelve-year old boy’s eyes welled up at the idea of seeing plaster casts made from the remains of deceased Pompeiians. I tried to remind him that Mt. Vesuvius erupted over two thousand years ago, and there are many more recent tragic and untimely deaths of friends and family members that were worthy of his tears, but for some reason, that didn’t make him feel any better.


In any event, our tour was amazing. We saw the main square (the “Forum”), the museum (“Antiquarium”), the homes belonging to wealthy Pompeiians, the brothels and the bakery. By the end of the tour, we could imagine how life had been for the citizens of Pompeii thousands of years ago.



Rome: Ah, Rome. If you had asked me before we got to Rome about our experience, I would have said that everything was perfect. Except for almost losing an arm in Paris, we experienced perfect weather, perfect lodging, perfect food, perfect itinerary. Then we got to Rome, and, let me just say that this is where our luck ran out. About everything.



First, the lodging. We had decided to stay in Trastevere, and I didn’t realize this area was the party capital of Rome and possibly all of Europe. I recommend staying here only if you enjoy a nonstop nighttime jamboree at decibel ten or are an avowed masochist.


Now, let’s move to the weather. The Weather app predicted rain for most of the time we were in Italy, and we didn’t get so much as an overnight sprinkle. Temps were in the 70s and sunshine was abundant. My husband and I kept saying to each other, Wow we are SO lucky! Then we got to Rome, where ALL THE RAIN we were supposed to get the previous three weeks CAME DOWN AT ONCE. We were on a Rome Street Food Tour and soon became saturated and blinded by the torrential downpour. For the three days we were in Rome, it rained 50 – 60% of the time. The good news is, if you forget to pack umbrellas or ponchos, vendors peddling said items magically surface all over Rome.


And…the food. I’ve heard it’s hard to find a bad meal in Italy, but leave it to my resourceful family to find one. We decided to try out a vegan restaurant, and let me be the first to caution you: NEVER be the only customers in a large restaurant in the center of a crowded town! That should have been our first indicator. But hungry people can make poor choices, so we rapaciously gobbled up our cardboard-tasting pancakes and eggless “omelets” and then fought each other, Roman Gladiator-style, for the prized bathroom in our lodging. Whatever noises were going on in there were at least drowned out by the nonstop party going on outside. That’s all I have to say about that.



And, oh right, the itinerary! How could I forget about our amazing Underground Colosseum tour, which we booked months in advance that


got canceled four days beforehand due to a nonexistent “political event”? My husband and I frantically searched for replacement Colosseum tours and were not surprised that everything was sold out. I mean, what kind of idiots would wait until the last minute to book a Colosseum tour in what was billed to be Italy’s busiest ever tourist season? NOT US!! I called the tour company that had canceled on us and spoke to a representative who made good on his pledge to find our family another tour. In the end, we were able to see the Arena floor but not the Underground section of the Colosseum. Apparently, Underground tickets only get released days beforehand and are snatched up within nanoseconds.

I don’t want to paint Rome as an entirely lost cause. We did have many good times there.



We enjoyed a pizza-making class and the previously mentioned Colosseum and Street Food Tours. We climbed the Spanish Steps and threw pennies in the Trevi Fountain. We toured the Vatican and saw the Sistine Chapel. And we learned, in-person, the answer to the age-old question of “What happens inside the Pantheon when it rains?”


So Rome – like the rest of Italy and Paris – was filled with great times and memories. Almost all of the food was amazing, the ruins were incredible, the sights were stunning. Yes, we were happy to be back in the USA, with its prevalence of clothes dryers and predictable weather patterns. But Paris and Italy will always live in our hearts, and our pennies in the Trevi Fountain have superstitiously assured us that we will be back!

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