I went to Italy for the first time and left with 5 regrets
NEWS | 20 June 2026
I never thought I'd be that annoying tourist until one afternoon in Venice. I didn't imagine I would regret touring the Colosseum in Rome. I couldn't have predicted I'd feel sour about spending one night in Milan. This was back in October 2022, when I took my first trip to Italy as part of a two-week backpacking trip through Europe. I traveled by train to four countries and spent six days exploring Venice, Rome, and Milan. I was just one year into my career as a travel reporter. I hadn't yet learned that I'd make mistakes on every trip — especially when visiting a new place — and that's OK. Looking back, my first Italian adventure could have been even more fulfilling and sustainable if I'd known a few things beforehand.
Author: More Stories. Joey Hadden. Every Time. Look Out For An Alert In Your Inbox The Next Time.
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