My DS has had Type 1 for 10 years now, since he was four. The pump was one of the best decisions we have ever made.
Really is no problem at all. We carry all of his supplies in a carry on bag for the flight (can’t afford to lose that!!!) and it goes through security without a hitch.
Seeing DS is always with us, I carry his meter, and a change of supplies with me in a fannie pack (he always has some source of quick sugar with him). Now everyone treats the insulin differently. We always make sure in the morning he has enough insulin in the pump to last the whole day. That way, we don’t have to carry it with us, worrying about keeping the vial out of the heat. (Another reason why we stay on site, so that if there ever was a problem, we could get back to the resort fairly quickly).
Feel free to pm me if you have any more specific questions. We’ve kind of been there, done that, and have pretty much ironed out the majority of the kinks.