How to plan a surprise proposal?

You should do a bunch of fake red herring almost-proposals to mess with her. She’ll be so surprised when the real one finally happens!

Personally if it were me, I would prefer to plan the vacation together and then surprise her with the proposal. But then I’m not one who feels a proposal or a wedding for that matter needs to be a three ring circus.

I agree with @janbb. I hate the attention and my ex husband proposed to me at home with just the two of us. It couldn’t have been better.

@janbb I was actually thinking something similar. I feel like that’s the only real way to propose to her in that setting and it still be a surprise. Plus, if we are planning it together, it would throw her off more than if I were to surprise her with a trip since that would be a raised flag immediately!
@Haleth I think she might get angry if I dangle it a whole lot lol. Maybe once or twice, but after that I could see that making her frustrated.

There is a lot to be considered. What sort of trip? Alaska cruise, EuroDisney, Holland by carriage, different settings are involved and different modes of travel.
What sort of people are you? If she is a florist, for example, a presentation of roses might not do much for her.
Lots of important details are missing.
I agree with you about the fake proposal idea. (sorry, @Haleth ) I would find such events irritating also.
Perhaps you could plan the trip, then propose when you present her with the trip details/tickets. That way she could embark on this trip as a new fiancé. I have a couple of ideas there, but it depends a lot on those other things whether any of my ideas might be a hit.

Sorry, I was being flippant. Don’t do that!

Surprises don’t always work. They can backfire. You had better be pretty darned sure she will stay yes, or it could be horrible.

This is a good idea. Implement your plan, then let me know it worked or not.

@Here2_4 I was gravitating towards more island/beach type trips since that is her preference. I also thought of doing it when presenting the trip/tickets but I think actually doing it there would be a bigger impact for her. I’m looking at a lot of places in the Caribbean.
@Haleth You’re fine! All input is good input. :)
@elbanditoroso Don’t worry. We’ve been together for a long time and have already talked about marriage so it’s an assured yes. I just want to make the proposal a very special surprise.

If she is a highly independent type, or a loner, then proposing someplace romantic during the trip would be ideal. If she is a nester though, with strong ties to family and/or friends, then she will want to share right away. In that case, you might want to make the proposal, and presentation of the trip at a family gathering, a formal dinner for instance.
Is she a nester?

@Here2_4 I’d say she is 85% Independent and 15% nester. She only has a few close friends. She has expressed that she likes romantic/intimate settings specifically for a proposal. Recently she was watching videos and said she wouldn’t mind immediate family being present. So she would like romantic(just us two) or something with only her immediate family there.

@RedKnight It sounds like your instincts are righ then. A planned trip, a romantic setting and pop the question. No need to overthink it.

So, If you are close with her parents, have them plan a great dinner. Hint you have something special to share at the dinner.
During the dinner, announce your trip. That way, the family gets to be with her for the beginning of it. Some women have to be able to share the exciting news of a proposal right away. This way, she has family with her when you break the news of your trip.
Better still, after dinner, have some time alone with her father. Tell him you want to propose during the trip, and ask him for his blessing/permission. Even women who have never said so, tend to feel more special about a proposal from a man who has asked Daddy first.
If you haven’t chosen where yet, look into Fiji. It is beautiful. The cabins on the water is a beautiful setting.
http://tse1.mm.bing.net/th?&id=JN.diY%2b6eBF8qRdhhFU0ONuBA&w=300&h=300&c=0&pid=1.9&rs=0&p=0

Thank you all for the help!

By the way, just my two cents, but I think a proposal should be just between the two people. She can always call her folks.

I had a barbecue a few years ago and a friend’s daughter texted from Vietnam that she was proposed to. The world is small.