YOU HAD ME AT 5 BOTTLES OF WINE (UPRIGHT). The perfect size for small family outings, road trips, or a 12-hour shift, this tall, square cooler is a great shape for stacking containers. Stash napkins, utensils, or chocolate bars (no judgement!) in the outside pockets for quick access. Remember ice packs! Because it squishes flat in your suitcase, we love the Pleasure Chest for travel, and it makes a great leave-behind hostess gift.