Vacation HELP!

My best friend and I are planning on going on a trip after graduation. We want to relax and celebrate our college graduation somewhere in paradise! I've never been anywhere out of the country so this is a very big thing for me!

Here's where I need some help! And, was hoping some of you guys could offer some advice.

Where do you suggest to go?

What websites or travel agencies did you use?

Did you do an all-inclusive vacation or purchase hotel/flight/food all separate?

What was the rough price of your trip and what should be the maximum to spend?
Suggestions on best/easiest/cheapest way to get a passport?

What did you do on your vacation?

Any other advice?

I've been looking into this trip for a few months now, but still have a lot of questions. I've looked into the all-inclusive vacations, but I don't like how the websites are set up based on picking destinations and travel dates. I basically want to pick a "range" of dates and several destinations and see prices/options, etc. Since I have never done this thing before, it's a little overwhelming and I want to get as much information as I can.

Any information will be helpful! Please and thank you! :)