Not that much advice to you, but I CRY when I leave my dog at the kennel, but the good news is he seems to love it, he runs right in without a glance back! It kind of offends me, to tell you the truth!!
We always bring his own food from home, a blanket that he is familiar with (the kennel provides dog beds each night, our choice) and a few special treats. The kennel we take him to allows us to pay extra for one-on-one play time, nature walks, and they have a doggie day care there as well that has an indoor play yard for the dogs that are behaved well and neutered/spayed of course!! We can pay extra to have him in that room as well. We usually give him 2 special things a day, it isn't that much more ($3.00) for each session and he seems to handle it much better, meaning he doesn't go on a food strike or anything like that. We call it the dog hotel (eases my mind a bit) and we also drive an hour to get to it.
He goes there two times a year, one longer stretch and a four day weekend here or there. He still likes it and doesn't whine when we pull up to the place, he actually gets very excited.
Good Luck to you, my only advice is really look around and find a place that you feel comfortable with. It makes it easier to leave them there. We looked around and this one was the cleanest, there were people there almost all the time (we went to a kennel several times to tour and there was never anybody around!) I also remember to book very early to reserve an inside/outside kennel, they are bigger and my dog can walk back and forth, inside and out. He is a bigger dog though.