It's actually her hotel that we're meeting at. So I won't have much control over what's in her room. Any advice to transitioning from the bar to the hotel room?
My plan is to open with confidence and initiate playful physical contact as soon as possible. Might even ask her for a walk on the beach before asking to go back to her room.
It's a good plan. Just lead the whole time and escalate.
As far as going back to the room goes...Obviously if your escalation works and you are getting ioi's then that should sort itself out on its own. If things don't go ideal, and she's like "Well, I should be going to bed soon." Then tell her you'll walk her back to her room. And whatever you do DON'T ask if you can walk her back, she'll just say she's fine. You basically escort her back, again, leading the interaction. Then when you get to the door you try to kiss close if you hadn't already, or stand there and try weasel your way into the room with her. You should be able to tell if its going to happen or not at that point, but some girls will have LMR and will push back a bit unless you really put some effort into getting in their pants. Good luck!