I've been to a lot of places. My favorites/best experiences were in Spain, Greece, and Israel. I actually prefer traveling alone, but I don't have a problem making friends in new places. In terms of meeting girls there, it's just better to have a crew of guys, as a lot of times they're traveling with a crew. If it's hard for you to make friends quickly, it's probably better to travel with friends. As an aside, I barely ever fap when traveling as you don't really have an opportunity.
I like to approach in park, there is a lot of space so no feeling of beeing in crowd or cutting someons space and loose atmosphere
When you attend concerts, make sure you sit near the front. That's where everyone else wants to be, and it gives you good views of the stage. Plus, you'll have a lot of people around you, so you won't feel alone.