I was never too crazy about Ft. Myers either. Would go downtown two or three times a year to meet friends. Most of the Ft. Myers locals hang out more at the bars and restaurants at Gulf Coast Town Center.
Another cool thing you may want to do is go to Everglades City and take an airboat ride. It's about an hour or so from Naples. Also, a bit further south (about 3 - 5 minutes from the Everglades City exit) there's a really weird/creepy wildlife sanctuary type of place. Dude who runs it is straight out of Deliverance. But the place is a blast. Has a HUGE python he'll let you play with sometimes and tons of other creatures all around the place. Everything from talking parrots to a killer turtle that has more jaw pressure than an alligator.
Also in Bonita Springs, there's Everglades Wonder Gardens. It's really cheesey, but cool at the same time. You'll see a ton of alligators and all kinds of animals. Pretty educational as well. Plus it's in the old section of Bonita (Old 41), which has a bit of character, and a good Mexican restaurant or two.
So you're familiar with Colorado? I live in Boulder. There are a ton of great drives around here. Some pretty harrowing along the cliffs. Enjoy Naples/Ft. Myers.
