My Italian Adventure and the Five Regrets That Followed

Never did I envision myself as the clichéd bothersome tourist until an incident during a sunny afternoon in Venice. Little did I know that a visit to the iconic Colosseum in Rome would end up on my list of regrets. The whirlwind night spent in Milan left a bittersweet taste, something I hadn’t anticipated.

Experience has taught me, as a travel journalist, that every new destination comes with its unique set of blunders. My inaugural trip to Italy took place in October 2022 amid a two-week European backpacking journey. I traversed four nations by rail, dedicating six days to three Italian cities: Venice, Rome, and Milan.

While the vacation itself was memorable, with a bit more planning, it could have been more enriching and eco-friendly.

First Misstep: Attempting to Explore Three Cities in Just Six Days

Trying to explore Venice, Rome, and Milan in less than a week turned the trip into a frantic dash. Starting with two nights in Venice, I sped off to Rome and then hurriedly caught a train to Milan, where I stayed for only one night before heading to another European escape.

This constant hustle left me feeling perpetually rushed and unsatisfied with a brief stay in Milan. Had I chosen a single city, I might have savored the experience more fully and been more considerate of my carbon footprint.

Industry expert Justin Francis of Responsible Travel emphasized to Business Insider that extended stays have less environmental impact and offer greater benefits to local economies, providing a more tranquil travel experience.

Aiming for October to Dodge Crowds Proved Unsuccessful

Given that Europe's summer crowds often swarm its top attractions, I assumed October travel, during the shoulder season, would spare me from long queues and crowded viewpoints.

My assumptions were misplaced. In both Venice and Rome, I navigated through dense foot traffic and waited my turn to glimpse historic sights. The apparent popular discovery of shoulder season suggests next time I'll visit Italy come winter.

Opting for Accommodation Outside Venice Wasn't Ideal

The allure of a castle stay just outside Venice for $360 was irresistible. Staying in the lofty quarters of Castello di Roncade was a dream, despite its half-hour distance from the city.

Despite the charm, I later learned that such choices inadvertently exacerbate tourism-related issues in Venice, without supporting local lodging businesses as much as staying in the city would.

Ill-Prepared for Local Customs and Norms

I mistakenly assumed that my general understanding of politeness was sufficient for foreign etiquettes.

After a Venice walking tour, I sought lunch but found no vacancies. I compromised with a gelato, intending to savor it on a secluded step, only to be gestured away by nearby officials—an inadvertent violation of Venice’s etiquette rules.

Abandoning a Strict Itinerary Led to Delightful Discoveries

In both Rome and Venice, my days were tightly packed with pre-arranged tours aimed at thorough sight-seeing. Yet, this left little room for spontaneous discovery.

When I reached Milan, I ditched my schedule and leisurely wandered the streets, hopeful for surprise encounters.

This spontaneity paid dividends. My unplanned visit to Castello Sforzesco—a stunning 15th-century fortress draped in foliage—not only exceeded my expectations but surpassed structured experiences elsewhere.

Looking ahead, open-ended exploration will top my agenda during future travels to Italy.