I would advise him as soon as possible of your pending travel dates. This is not something you would just drop on someone at the last minute. Advise him of the dates that you will be away and if you feel like you need to tell him anything else, just advise him that you are going away w/your church group. Nothing more.
You had the opportunity to go away to Florida and you didn't do it because of work. Now, it's time you starting thinking of yourself and this short trip will do you a world of good.
He's a big boy and he can handle the business for a couple of days. Nothing earth shattering should be going on during that time and if it does...he can handle it. Time he realized what you bring to the company.
Magic, you worry entirely too much about what he thinks of you and what he's going to say to you. You are a grown woman and you know what? You need to get a life, a life w/some fun and socializing in it and this is the perfect trip for it. Go and have some fun.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.