I won't leave Jackson in a kennel/boarding type environment, just because he's the kind of dog that does NOT do not well in those kinds of situations. I can not even hand him over to the groomer, or vet, without him expressing his anal glands (yuck!) out of fear. He doesn't like to be handled by strangers at ALL, he's extremely sensitive, he hardly even likes ME to pick him up (but does allow me). Just too much stress. Plus I know some people that work at those places, and I'm not sure I'd be thrilled leaving them up to taking care of my dog to be honest.

I'm very lucky that I have my dad. He's the only one I trust to REALLY watch him well and I know Jackson is happy there. My dad said he really misses me though - he's different without me, and does a lot of window watching. BUT, he's overall happy and my dad is honestly probably his #2 favorite person in the world. I've left him sometimes just for one night at a time, I think the longest was around 10 days.

I love him, and he and I are completely attached at the hip. He's my boy. But sometimes it IS nice to have a little break. I really start to get my own separation anxiety though after 3-4 nights lol.

If I didn't have family, my next option would definitely be an in-home pet sitter. I'd have to have the person come meet him a few times with me present, and then he'd be more comfortable.

Attached
 

Yes, you talk about attached! I can't even go to the bathroom without my Gizzy going with me! He is very attached to me and it scares me. I also start missing him and have to come back home from where I go after about 2 hours. I want to take him with me sometimes to visit my friends and family but he tends to throw up.

I have left Prince with my mom one time...Ricky's never been left since we had him. My mom has 2 yorkies and used to watch Prince and his former siblings when his old owner would leave town. He does quite well there as my mom and step dad are pretty much the only other people Prince likes. The only problem is that it's an hour and a half drive to drop them off and my parents are usually not on my way to where I am going.

I have a free nights stay at a Casino in Detroit...only 20 minutes away from me...and it needs to be used by March. I'd love to go stay the night and gamble...but I don't know what I'd do with the boys. Prince is the main problem because he is scared of strangers. I am not sure anyone could get ahold of him to put a leash on him to take him outside to potty. I've got someone willing to stay the night....but I am not sure how they'd fare alone...I know, I keep thinking it's ONE night...and I'll only be 20 minutes away in case of an emergency. I will probably try it...but it's going to be tough.

I know one thing...the boys wouldn't do well in a boarding environment. The perfect place for them is another house where they have other little dogs to play and interact with. I think that's why Prince has done so well at my moms when he has such a tough time elsewhere.

I too was very upset about leaving my Sophie to go on a holiday. Although I had a lot of friends to look after her i just did not feel they could do the job I do! We looked into doggy day cares. As good as they are I was still concerned about her getting hurt, not eating etc.
We finally decided to kennel her at our vet who does this for his patients only. We first left her at 7 1/2 months for a week. I cried for the whole week of my holiday and my husband actually wanted to come home early. We called every day (Skype) and were assured she was doing just fine. WE ARE THE ONE HAVING THE SEPARATION ANXIETY NOT SOPHIE I CAN HONESTLY SAY. She did just fine! We have since just come back from 12 days in Hawaii. My vet laughed and said I was the only one they knew who cried going to Hawaii:D Again we called everyday and they also send us pic's. They let her run around while doing chores and we have her walked weather pending. This time when we came back she was solo excited to see us. Then............. she went behind the reception desk to say bye/hi to all her new family and proceeded to go back to where her play time and kennel was. Guess she did not miss us as much as we missed her:roll eyes: When she did not eat as much they would give her special gastro food. At least if she ever did get the runs or stopped eating "they" could handle the situation as required. Her personality has not been effected in any way and she goes right back to her normal routine. I actually feel she has become more independent now and does not require attention 24/7. Only 12/7 now. If you feel comfortable with your vet it DOES NOT effect them to kennel. We as owners just love them so much we are the ones not letting go. Just mine and Sophie's opinion.