Chris-
If it helps, my DS8 just got back from a week long sleep away camp. He was gone 6 nights Sunday afternoon to Saturday morning. He begged us to be able to go and everyone we know thought we were totally insane for agreeing. He has NEVER spent the night anywhere else and we weren't sure he'd make it through the first night, let alone a week but we gave it a shot.
He LOVED it. I mean really loved it. Three weeks later I'm still getting "Well at camp they..." for everything. He didn't cry once, wasn't homesick and didn't seem to care. He wants to go back next year for TWO weeks!
I would want to know what the plan is for homesickness. The camp my DS went to had a very serious tiered plan from distraction to when and why they would call home. The first call home is from counselor to parent only and the child isn't allowed to call. The second call is the child, monitored by the counselor. THey pretty much will not consider sending a child home until after the second night. By then, anyone who is homesick gets the "Oh come on, you made it this far! You can totally do it, let's go get a cookie and go for a kayak on the lake!"
Send your son with whatever comfort item (blanket, pillow, stuffed animal etc) that he is used to! If you can send mail do it early so he gets something day one. I also packed little notes in his suitcase for him to randomly find, like stuffed inside his shirt or his socks. Nothing cheesy or embarassing- just little riddles or notes from home.
He'll be okay :-)
