Milan-Lake Como-Portofino-Rome: An Italian Itinerary to Remember

Planning the perfect trip to Italy

We had experienced Italy’s big three: Rome, Florence and Venice. Undoubtedly, these cities are the building blocks of a great Italian vacation for first-timers.

Craving a slightly difference experience, we decided to head off the beaten path to discover more of what this boot-shaped country offers.

Greatest lesson learned: There are no bad choices in Italy. Each stop is delicious and intoxicating, even without the wine.

There’s something about Italy. The cadence of its song-like language, the casual-yet-passionate attitude of its people, the beauty of its landscape reflected in its art and architecture, and its uncomplicated, fresh food.

For this Italian adventure, we incorporated fashion-forward Milan, drop-dead-gorgeous Lake Como, enchanting Portofino and historic Rome. It ended up being a winning itinerary because of the destinations' variety in size, pace and things to do.

We started and ended with big-city touring, but the heart of the trip gave us ample time to hike, reflect and soak in the beauty of the quainter side of Italy’s smaller villages.

Here are a few highlights of what make these destinations special.

Milan: where modern Italy thrives

Milan Duomo rooftop
Milan blends old and new beautifully. There's no better spot from which to admire the city than the duomo's rooftop. We could have spent hours there.

The Last Supper by Leonardo da Vinci
You may only get 15 minutes with Leonardo da Vinci's The Last Supper, but it's worth planning ahead to get reservations to see it. Viewing groups are limited to about 30 people, making the experience even more special. To ensure the fresco's preservation, our group passed through two dust-collection chambers before entering the cavernous room.

Galleria Vittorio Emanuele II - Milan shopping at its finest
Galleria Vittorio Emanuele II is the world's oldest shopping mall. Fashion and art come together in this lovely space.

Apertivo at the Bulgari Hotel in Milan
Cocktails in Milan come with a spread of treats like this one at the Bulgari Hotel. The Milanese take their apertivo time heartily.

Lake Como: deep beauty

Grand Hotel Tremezzo, Lake Como
We absolutely loved our stay in Lake Como at the Grand Hotel Tremezzo. Gardens, pools, a sandy beach and plenty of dining options made it difficult to leave the hotel.

Lake Como boat tour
Touring Lake Como by boat is a must. The lake covers 56 square miles and is one of Europe's deepest lakes at 1,300 feet.

Varenna
Varenna is one of the fishing villages along Lake Como that deserves ample time to explore.

Romantic dining at La Terrazza
Dinner at La Terrazza in the Grand Hotel Tremezzo is one of the most romantic places we've dined. We were lucky to be there during a full moon so we could watch it rise over the mountains as we ate.

Portofino: poshness with plenty of active pursuits

Harbour of Portofino, Italy
Harbour view in Portofino

Hiking Cinque Terre
Hiking Cinque Terre is no walk in the park, but it's worth the effort. We hiked from Monterosso to Vernazza.

Vernazza, Italy
Vernazza is one of the jewels of Cinque Terre.

One of many scenic view along hike from Portofino to San Frutuosso
While we enjoyed our Cinque Terre experience, an even better hike is from Portofino to San Frutuosso. We practically had the trails to ourselves and were rewarded with views like this one.

Pesto lasagna at Da Laura in San Frutuosso
The perfect ending to our hike was a lunch of freshly caught mussels and this amazingly fresh pesto lasagna paired with local white wine. Magnifico!

Rome: where it all began

Trinità dei Monti church atop the Spanish Steps
Rome glows at sunset from the vantage point atop the Spanish Steps. It's one of our favorite spots in Rome at this time of day.

Pantheon
The almost 2,000-year-old Pantheon dome, the world's largest unreinforced concrete dome, amazes me everytime I see it. The height to the oculus, the building's main source of light, and the diameter of its interior circle are the same at 142 feet.

Roman Forum - Temple of Antoninus Pius and Faustina
The grand scale of the Roman Forum is a thrill to walk through and imagine what life was like at the height of the empire. I loved watching the clouds pass over the Temple of Antoninus and Faustina during our visit.

Egg-filled ravioli at Trattoria Monti
Egg yolk stuffed into a ravioli topped with a black truffles at Trattoria Monti is a genius move. I couldn't think of a tastier way to end our trip.

While the temptation is always to return to the same beautiful places we've visited, this trip has us scouring Italy's map for new spots to explore. Our eyes have been opened to how much more there is to see in this country. We look forward to our next adventure!

Which are your favorite Italian cities?

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