What's in my Carry-On “I’m packing for 21 days in Greece — an early spring road trip through ancient ruins, medieval villages, and mountain monasteries, with a stop in Santorini including a full day on a catamaran. Cooler temperatures, long drives, and a few really special dinners. Here’s exactly what’s in my bag. Six tops. Three bottoms — plus a pair of lightweight joggers for the catamaran day. Two dresses for the days I want to feel a little more elevated or for nicer dinners. Two pairs of shoes: a walking sneaker that handles everything, and a black mary jane flat for evenings. Four outer layers in different weights — a packable down jacket, a black cardigan, a black wrap trench for dinners, and a rain layer. Plus the obvious: one bathing suit, underwear, pajamas. Last minute I threw in a pair of pool sandals — and I swapped that black raincoat with my cream one because it was too heavy for this trip. One carry-on, twenty-one days!