Well I think it's great that you are doing a trial this weekend. It will make it a little easier on Schatzie when you do have to leave her for vacation.
We had to leave Hercules at the end of January to go to CA for my boyfriend's brother's wedding. I found a kennel in MD (thanks to YorkieRose's recommendation) that only boards small dogs. I went and checked it out ahead of time and felt completely comfortable. The let the dogs out most of the day (except for a 2 hour nap time during the day) and then are in the kennels over night. It was one of the hardest things I ever had to do. I cried my entire way home. And I thought about him the entire trip.
I know it will be rough, but at least she will be with the breeder. That should make it a little better for her.
Look forward to the fact that you'll be in JAMAICA!!