Imagine
You have Bailey take something of yours on the road with him. It can be a stuffed animal that you got him for his birthday or a shirt of yours, just so that he has something to remind him of you and smells like you. This trip you gave him your backpack with one of his favorite hoodies that smells like you and little notes in his luggage (specifically in his pants and hoodie pockets), (see the picture above). This is just in case he starts to miss you while he's gone, now he has you in his pocket even if you aren't able to see him till he gets back.