Talk to your child about some special things that he can do with the caregiver. This might mean a trip to the zoo, baking cookies, or anything else that is special to your child.
Tell your child exactly when you will call to check in. Make sure that you do! Let your child know that the caregiver knows how to get in touch with you.
If he’ll be staying away from home, pack up all his necessities so that he can see that his favorite cup and other comforting items will be going along. Make sure that the host has other familiar essentials: the right kind of milk or juice, his favorite fruits and snacks, and maybe even some food allowed only on special occasions.
Be sure to include a small photo album in your child’s suitcase, just in case he needs to have some “visiting time” with you.
With your child’s help, make a “sleepaway book” about what’s going to happen while you are away. Include photos of whom he’s going to stay with, where he’ll be staying, and what he’ll do. Have him draw pictures for the book as well, and look through the book several nights in a row before you go. By the time you leave, your child should be really clear about what to expect.
Make a “sleepaway chart” that will let him keep track of how many days are left before the end of the trip. Give him stickers or a marker to check off the days at bedtime. He can also use this as a scrapbook to record memories of the time spent with the caretaker.