Hi L. - Your grandson will have so much fun at school, but be prepared for a transition! Get the list from the school - if they don't have one, get in touch with the director and/or his teacher to ask what they really need there. For our 4 year old, the following goes to school with him - his "nap" bag, which includes a sheet, a small pillow and a blankie just for school naps on his cot(in case there is A/C or school is cold) -this is sent home every week with him to get washed - the bag should be big enough for the child to easily be able to take things out and put them away in it. We don't send toys - school discourages and they can easily get lost. As far as lunch, our school will not serve candy, but you can put a "treat" in there if they eat their "growing" food - chocolate pudding is a hit, those small 100 calorie packs of cookies are good too. You can make sandwiches (make sure PB isn't banned because of nut allergies in the class - sunflower nut butter is a good sub), you can get a thermos and send mac/cheese, ravioli, etc. we get a cheap plastic sandwich box from target to go with the lunchbox (we get the softsided ones with characters, need blue ice to keep things cold, a juice box, etc.) He needs extra clothes, undies, socks, shoes, etc. LABEL EVERYTHING - put in a gallon size ziploc. Our school encourages easy on/off clothes - like drawstring pants, so the child can go potty easily and learn to be independent. A picture of you, other close family members, pet, etc. to put up in his cubby is also a great idea in case he gets a little bit sad - this is a very exciting time - he will make new friends and have lots to talk about with you at the end of his day (and will bring home more artwork than you can even imagine!) - good luck and be confident that you are doing the right thing!!