At the Città Alta, cobblestone lanes wound through cafés, markets, and medieval towers. We stored our luggage near the station and spent the morning wandering narrow streets lined with artisan shops before grabbing our first Italian espresso (and the kids’ first gelato, of course). From its ancient Venetian walls to its panoramic views of the Lombard plain, Bergamo was the perfect gentle welcome to Italy — steeped in history but full of life.

By late morning, we boarded a Trenitalia regional train to Milan, the city of style and ambition. The hour-long ride brought us into one of Europe’s great powerhouses — not only the capital of fashion, but also a place with deep ties to modern history. Milan was heavily bombed during World War II, and after the city’s liberation by Allied forces in 1945, U.S. troops helped secure northern Italy as part of the broader campaign that ended Mussolini’s fascist rule.

After checking into the Sheraton Diana Majestic, we explored Galleria Vittorio Emanuele II, one of the world’s oldest shopping arcades. Its glass dome and mosaic floor shimmered with afternoon light, surrounded by the buzz of shoppers and the sound of clinking espresso cups. Beneath its elegant coat of arms tiles — representing Italy’s great cities — the kids spun on the bull of Turin mosaic for luck, a Milanese tradition said to bring fortune (and smiles to passing tourists).

By sunset, we were sitting outside a café, watching Milan’s golden hour reflect off cathedral spires and polished marble — realizing that this first day was everything we’d imagined Italy to be: history, beauty, and a thousand little details that feel timeless.

Short bus ride away to Milan.