Italy has a way of pulling you in—sometimes with postcard‑perfect coastlines, sometimes with Renaissance masterpieces, and sometimes with crowds so dense you wonder if the entire world booked the same vacation week. Our trip through Cinque Terre, Pisa, Florence, Venice, Milan, and Lake Como was a blend of beauty, chaos, daily gelato, and trains that were never on time.

Cinque Terre

We started in Monterosso, the most beach‑friendly of the Cinque Terre villages. The water was perfect, the sun relentless, and the crowds omnipresent. Our Airbnb sat right on the beach, giving us quiet mornings and late‑night views before the rush began. The view was incredible.

On the first day, we grabbed lunch in the old town at La Cantina del Pescatore, and the food was a bit disappointing. I wouldn’t recommend it. For dinner we just grabbed some local fried sardines and a focaccia and they were a hit with some local beer.

The next day we started our Cinque Terre adventure, which was part trains, part hiking, part boats, all stunning.

First, we took the train to the last village Riomaggiore. It was still pretty early in the morning and we were still full of energy, so we marveled at the colorful houses, steep streets, iconic views.

From there we did the coastal walk to the next village, Manarola. The path was mostly in the morning shade and right along the rocky cliff. It was the kind of path that makes you stop every few minutes just to stare.

In Manarola, we explored more steep streets, colorful houses and plenty of lazy cats. We found a playground with the most amazing view.

From Manarola we took the train up to Corniglia, perched high on its hill like it’s guarding the entire region. Thankfully, there was a shuttle from the train station to the town, otherwise the walk would have been brutal. We walked the narrow alleys and stumbled upon a gelato place. S couldn’t resist trying it. He survived on french fries and gelato on this trip.

From Corniglia we hiked to Vernazza, a 2.2 mi trail with sweeping sea views and colorful villages tucked into cliffs, however, in the middle of July with the temperatures in the mid-30s C (95F), the hike proved to be harder than expected. I can see how this can be a nice hike in cooler weather. In the summer it’s a hard pass. By the time we reached Vernazza, all we wanted to do is get on the boat to Monterosso.  

Exhausted, we took the boat back to Monterosso, the perfect way to end the day with the coastline unfolding beside us. We spent the rest of the day at the beach.

Cinque Terre is beautiful, but it’s also busy. Still, the mix of trains, trails, and boats made it feel like a true Italian coastal adventure.

Pisa

Pisa was a quick stop on the way to Florence. We climbed the Leaning Tower, which is steeper than you expect and slightly disorienting as you spiral upward. The surrounding buildings—the cathedral and baptistery—are equally impressive. It’s touristy, yes, but worth doing once. On the way back to the train station, we got some nice sandwiches to go at L’Ostellino Pisa.

Florence

Florence was a dream. We stayed near the Duomo, which meant waking up every morning to one of the most recognizable silhouettes in Europe.

The city is dense with history and art, and we made the most of it:

Saw Michelangelo’s David in the Galleria dell’Accademia. S had a lot of questions about the origin of clothes and their lack of in all the statues.

Wandered through the Uffizi Gallery and saw Botticelli’s Birth of Venus.

Walked across the Ponte Vecchio.

Climbed the never-ending steps of the Brunelleschi’s dome. Florence looked fresh after a brief rain shower.

Found a tiny hole‑in‑the‑wall wine stop that felt like a secret.

Explored Palazzo Vecchio. S and E, in a burst of ambition, climbed the tower of the Palazzo Vecchio—because apparently one iconic viewpoint per city wasn’t enough; however, according to them, the climb was not worth it because the view was not accessible.

S hopped on the carousel in the Piazza della Repubblica. Even the carousel felt like a piece of art.

Finally, enjoyed a delicious dinner at Buca Poldo restaurant we still talk about. The appetizer, pasta and osso bucco with beans were all delicious. The first really good meal in Italy.

Florence is the kind of place where every corner feels like a painting.

Venice

Venice is exactly what you imagine: canals everywhere, narrow alleys, and crowds that move like slow tides. We arrived in Venice around sunset and were treated with a beautiful sunset sky.

The next day, we started with the historic center, including Saint’s Mark Basilica covered entirely in mosaics that shimmered in the sun.

We crossed the Rialto Bridge, and took a traghetto across the Grand Canal to get the experience of riding the gondola.

Explored Doge’s Palace with its impressive size and gothic architecture.

Grabbed lunch at Bar All’Arco and Cantina do Mori (because why not try two places) – yummy open-faced sandwiches.

We went to San Giorgio Maggiore Church to get a glimpse of Venice main area from afar.

Rode the elevator (yay!) to the top of St Mark’s Campanile to get a viewpoint overlooking the Piazza San Marco and the city’s maze of burnt orange rooftops. By the end of the day, ‘tired’ was an understatement.

It’s chaotic, but Venice’s charm is undeniable.

Milan

Milan felt more modern, and definitely more expensive. We stayed near the Duomo di Milano, which is breathtaking from the outside but even more impressive when you climb onto its rooftop. The gothic details are intricate, almost lace‑like, stretching across spires and arches.

We sipped an Aperol spritz at Bar Camparino inside the elegant Galleria Vittorio Emanuele II.

Then visited The Last Supper. Seeing Leonardo da Vinci’s masterpiece in person is surreal, even if the painting is more faded than expected.

Lake Como

Lake Como was a highlight. We took a boat to Villa del Balbianello, famous for its immaculate gardens and cinematic views. A few Star Wars scenes were filmed there, and it’s easy to see why—it feels otherworldly. It’s also a popular engagement spot. A couple handed me their phone and casually asked me to take their picture. The guy then proceeded to get on one knee and proposed to his girlfriend.  

We visited Villa Carlotta in Tremezzo, less luxurious but still charming.

Then came Bellagio. Stopping there on the way back was a mistake. The line for the return boat was insane. We stood for an hour in the scorching sun, packed shoulder‑to‑shoulder with other travelers all trying to get back to the train station. Beautiful town, but the crowds made it tough to enjoy.

Italy is a country of contrasts: beautiful beaches and packed piazzas, ancient art and modern fashion, serene lakes and chaotic tourist lines. Crowded? Absolutely. Worth it? Without question.