Ooo, girl. That is JUICY! I love a good story of an internet romance.
Now, obviously my first piece of advice on all of this was going to be that you make sure he's not catfishing you. If you've Skyped a bunch of times and sent a ton of photos, you know he is (probably) who he says he is; or, at least, that he exists. So I'm not that worried about it from that perspective, but you can never be too careful.
That being said, you have to do some things for me and the people who love you. Your friends need to know which hotel you're staying at and your room number, and you need to sync up your phone so they have a pin in your location for the entire weekend. You promise you'll do those things?
It may sound like overkill, but your life and safety are NEVER to be taken lightly. If you tell me you're planning to go to where he is and not tell anyone, I will scream. Going to hotels with strange men you think you know is how you end up becoming the real-life inspiration for an episode of SVU. Spoiler alert: You're the body.