Eloping

I don't think there's any way to gently break the news, you just have to rip it off like a bandaid. Of course making this decision is going to cause some hurt feelings, but it sounds like that's something you're prepared for. People will voice their opinions and then they will get over it.

Well I told some of my close friends and family and even though I know they would want to be there when I explained our situation they understood. Now his mom and sis do not know yet so we will see but he is dead set he does not want a ton of eyes on him so hoping they'll understand. I would say tell them in person and expect some feelings may be hurt but let them know this is what you want to do. I would at least include them in important things like dress shopping or something. Have you considered eloping then having a post elopement party? That is what we are doing and we know that some of the people I have told like that as it is a way to celebrate even though not everyone will be there.

I would make an announcement afterwards. There are a lot of "We Eloped" cards online that are super cute.

I would definitely tell them in advance! To be frank, expect your family to be a little deflated that they will not be able to partake as it is a big event that most parents (and siblings etc) wish to share with you.

I think not telling them until after your elopement will only rub salt in the wounds.