Get a soft-sided cooler, not a bento box

For travel or vacation days out, the best lunch box is a soft-sided insulated tote with a waterproof lining, not a hard bento box.

Bento-style boxes are great for desk lunches, but they’re the wrong tool for a day out. They’re rigid, so they take up the same space whether full or empty, and they tend to leak at the seams when you’re jostling around in a car or on a train. Soft coolers fold down when you’re done, hold more awkward-shaped food, and are much easier to stash in a backpack or beach bag.

If you want a specific model, the PackIt is my usual pick because the built-in freezer packs mean nothing gets soggy. The Yeti Daytrip is more expensive but basically indestructible. Either way, look for a waterproof interior and a durable zipper — you’ll be tossing this next to sunscreen and a wet swimsuit, and you don’t want melted ice ruining everything.

Keep it under 10 liters if you’re flying or taking transit. That’s plenty for sandwiches, snacks, and a cold drink, and it still counts as a personal item. Future You will be glad you didn’t haul a hard plastic box across town.