What do you want a huge posse of dudes for, unless you're seeking advice on how to pick up men? I have no advice on this as I am not gay. Generally, "wingmen" get in my way or gawk annoyingly rather than doing anything productive. I've found them be a pain in the ass in general. It might seem scary to go out alone, but really it is easier. I can only think of one time a wingman was truly nessicary and I didn't end up getting laid out of the deal anyway so....
As far as vacations, just take a woman with you or meet people once your flight is in. Plane rides can actually be a good place to meet women. Fly down to South America, you can meet all kind of women with no wingman needed or set up a bunch of Internet ladies in some random US city and then go bang them all one after another. There's too much pvssy to be had to be worrying about dudes imo
