... Sometimes, if I'm at the top of a mountain, I'll make a few contacts and have others marvel at the range I'm getting...
That is one thing about your standard handheld 5 watt 2M ham radio (HT) - you'll get some range without line of sight, but it is on the order of a mile or two. With line of sight, and a large clearance zone around the line of sight (as in peak to peak), we routinely talk at 90+ mile range using hand-helds with a 19" whip antenna substituted for the stock antenna.