Most luggage includes a zippered or mesh pouch that is excellent for storing a pair or two of shoes. For a Caribbean trip, I typically pack a pair of sneakers and a pair of sandals or flip-flops, unless I'm planning on hiking (in which case I would wear my hiking boots and pack my dress shoes). I have found that I can usually squeeze two pairs of shoes into the zippered compartment, or one pair of shoes plus a toiletry bag.