GeneralJune 20, 2026 · 11:12 AM1 min read

    I went to Italy for the first time and left with 5 regrets

    I spent six days exploring three cities in Italy — Venice, Rome, and Milan. It was my first time visiting the country, and I left with regrets.

    By Joey Hadden

    I went to Italy for the first time and left with 5 regrets

    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.

    Source: Business Insider · General
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