Woman Packs Long Red Gown for Italy Trip, Never Wears It Once

KEY POINTS

•Chloe Caldwell has been traveling regularly to northern Italy for three years and reflects on what to pack.
•She found a compact umbrella, a multi-outlet Tessan travel adapter, and a selfie-stick tripod essential for convenience.
•Her packing mistakes include bringing a long red gown unworn for two weeks and two pairs of white sneakers that got dirty.

Chloe Caldwell, a frequent northern Italy traveler, has mastered the art of overpacking like a tourist champ despite repeating the ritual for three years straight. On her latest two-week escapade with trains, spritzes, and cobblestone struggles, she packed essential survival gear like a compact umbrella—not exactly a flimsy luxury brand but good enough to not drown mid-stroll—and a phone tripod doubling as a selfie stick, because obviously, strangers can't be trusted for photos without thumb photo bombings. She boasts a luggage-suitcase-flap-backpack tag-team solution to drag baggage through Venice's ancient cobbles, rotating between her Beis and Portland Gear backpacks. Notably, she slaves over her footwear decisions packing two pairs of white sneakers, which quickly get street-murdered by Italy's welcoming dirt, plus that infamous long red gown that survived two weeks untouched, a sobering monument to fashion folly. Bonus? She wields a Tessan travel adapter that accommodates phones, hair tools, and anything needing juice, folding compactly to remind her that even adapters aspire to be travel-friendly.