When I told people I was going to Italy, the reaction was always positive–something like “wow!” or “oh that’s awesome!” People know Italy has the good stuff. From amazing cuisine to endless history and culture to explore, it’s easy to understand why Italy is such a popular destination.
I visited Italy back in 2019, but this trip was a chance to do more. My wife and I planned a trip from Florence to Rome with plenty of classic sightseeing and a bit of time to get outside the big cities.
Fine Art in Florence
We started our trip in Florence, the capital of Renaissance art! Ever since I first visited the city, it’s been my favorite style of art. Allow me to nerd out for a moment.
In Florence there’s this amazing transition from the mystical and symbolic world of medieval art to the realistic and human-centered art of the Renaissance. Artists looked at Greek/Roman art and said, “hey I could do that!” You see famous works of art all around the city, and you start to understand why the rest of Europe was soon swept along in a “rebirth” of art and culture.
Our top priority was visiting three of the most popular sights in town: the Accademia Gallery, the Uffitzi Gallery, and the Duomo complex. This trio houses many of the most important works of art, and all three require a certain amount of advance planning to manage the intense crowds. (Which obviously we did because I’m great at trip planning.)
The Accademia Gallery felt the most crowded, but I’m happy to report that seeing Michelangelo’s sculpture of David was totally worth it. What a sculpture! The Uffitzi Gallery is my personal favorite because of the tremendous collection of Renaissance paintings. What surprised me the most was the Duomo Museum–it’s definitely underrated. You get to see the originals of Ghiberti’s “Gates of Paradise,” statues from the cathedral exterior, and an in-depth look at how the famous dome was constructed.
Over to Oltrarno
The downside of Florence is that the compact city center is always crammed with tourists. Like, I can’t blame them, but it did get tiring after a while trying to walk through all the crowds.
The solution? Head over the bridge to Oltrarno. It’s a neighborhood that has tons of character and significantly less crowds. Old buildings line narrow streets where you pass little wine shops and the workshops of traditional craftsmen.
My first encounter with Oltrarno was back in 2019, when I joined a food tour on a whim and loved it. So it was an easy decision to book another food and wine tour to check out some new places. We enjoyed meats and cheeses, a bit of rustic pasta, and a few glasses of Tuscan wine (more on that later).
Of course, there had to be gelato for dessert. Italy has truly perfected the art of making ice cream, and Florence in particular does gelato at a very high level.
Cinque Terre
The Cinque Terre is a place I’ve dreamed of visiting for a long time. These five picturesque towns cling to the rugged coast, linked by hiking trails that wind through hills and vineyards overlooking the Mediterranean. I was so excited we could fit them into our trip!
Unfortunately, the weather was not on our side at the start. It rained all day when we arrived, and we wore raincoats as we sloshed around our home base of Vernazza. Their small fleet of fishing boats were all pulled out of the water and into Vernazza’s main square to protect them from waves crashing against the breakwater.
Thankfully, I am happy to report that the rain stopped by morning, and we headed out for a big day of hiking. I was honestly not sure how far we could hike. We planned a tentative route from Vernazza to Manarola, about 10km of steep hiking along the hills. But the views on this hike made it seem easy.
We climbed up above Vernazza, passing old olive trees and tiny vineyards enclosed with stone fences. Here and there, the trail opened up to a view of the next town, another clutch of colorful buildings perched above the sea. It was magical.
After stopping for wine along the trail (yes, that’s a thing), we made it to Manarola for a mid-afternoon lunch. We decided there was just enough time to add on a stretch of the Via dell’Amore, a trail that was recently re-opened. This trail runs right by the shore, a romantic stroll along the sea cliffs and the crashing waves below.
It was one of those moments where I just stopped to appreciate that we made it to such an amazing place.
Time-out in Tuscany
I have to admit this: visiting Tuscany was my wife’s idea. I was a bit skeptical of taking a few days to lounge around drinking wine and tour around the countryside. It ended up being a surprisingly awesome part of the trip though.
We rented a car and based ourselves in the hilltop town of Montepulciano. Guys, I really liked this town. It has cool Renaissance architecture, amazing views of the countryside, and ridiculously good wine. Also, fun fact, I learned that the movie Twilight: New Moon was filmed there.
But back to the wine–Montepulciano produces some amazing ones. We loved the Vino Nobile de Montepulciano, an aged red wine that I would describe as both complex and very drinkable at the same time. We toured a couple of the wine cellars where they age their precious product in giant oak barrels. It was fun comparing the different local wines, which were quite distinct depending on the specific vineyards and aging processes used.
We also spent a day touring around the countryside area known as Val d’Orcia. Visually, it very much lives up to all the cliches: rolling hills topped with stone houses, winding drives dotted with skinny cypress trees, and row upon row of grape vines. “It looks just like Olive Garden!” I joked as we drove by. We followed a route suggested in the Rick Steves guidebook, and there were lots of places to stop and take in the views.
We also detoured to the town of Montalcino for, you guessed it, more wine! The famous Brunello di Montalcino is a powerful red wine, with lots of dark flavors that arise from a long aging process. Would recommend.
While I’m usually all about the sightseeing, it was nice to relax a bit. To use another cliché, Tuscany really felt like la dolce vita, a place to slow down and savor the simple good things in life.
The Eternal City
For our grand finale, we took the train to Rome. It’s a city that needs no introduction, and a city I really enjoyed visiting once before. To a history nerd like me, there’s really no place like it. But Rome is not exactly a secret, so there are always lots of tourists trying to enjoy the same things at the same time.
Let’s start with something not historical or crowded: food. Eating in Rome is awesome! We kicked things off with a food tour, which I always think makes a perfect introduction to a city. We started off with an aperitivo in the famous square of Campo di Fiori and made our way over to the neighborhood of Trastevere for some local pasta. Amatriciana, cacio e pepe…trust me, you want these things when you visit Rome.
We also ate well in Monti, the neighborhood where our hotel was. I enjoyed our mornings drinking coffee in a cafe, sipping a cappuccino and eating a cornetto (don’t call it a croissant). I will confess that that one morning I got American-style eggs and bacon, but I needed plenty of energy for a day of sightseeing.
The Eternally Crowded City
And the sightseeing was a lot. I was prepared for big crowds, but I did not anticipate how much they started to bother me. The first place I really noticed it was at the Colosseum. It was hard to walk in, crowded on every staircase, and even difficult to find an open bit of railing to view the massive structure. The Colosseum is one of the most impressive landmarks in Rome, so the popularity is understandable. But yikes!
The Vatican Museums were even worse. The crowds were wall-to-wall, a huge conveyor belt of people all lumbering toward the Sistine Chapel. We went with a guided tour, and our deadpan guide warned us to “conquer your space” and make sure to take pictures along the way. Overall, I think braving the crowds was worth it to see the amazing art (I mean, it’s the Sistine Chapel!), but the experience was stressful.
Fortunately, there is a solution to the crushing crowds in Rome: take things slow and explore away from the biggest sights. I enjoyed strolling through neighborhood squares, popping into lesser-known churches, and sitting down to enjoy the aforementioned restaurants. Rome is a beautiful city, with so much to see beyond the most famous places you see on TikTok or wherever you get your travel content.
And that’s basically a theme that ran through the whole trip. Italy is wondrous place to experience, and truly lives up to the hype that makes it so popular. But even a few steps off the well-worn path of tourism made for some magical moments of travel.
