I used to be more adventurous in my younger days. My first trip to the island I went without hotel reservations but didn't consider that adventure, it seemed normal to me and it worked out great. I've never been a "mainstream" traveler so I shyed away from large resorts. My adventurous spirit is more what I do as opposed to where I go - getting to know people who in turn turned me on to great off the beaten path things to do. I was introduced to Little Bay and Orange Hill years ago and they became my "getaways" from Negril. Enjoyed doing really unique things like dirtbiking the trail to Little Bay (off road), venturing to parties in Orange Hill (those great street parties where the whole community comes out) - we even took a boat to Little Bay once and that was a pretty funny adventure. I have a friend who has a zodiac and for many years that's how we'd cruise the Black River, going places on that river that only residents knew about. I'm not one for guided tours - where ever I've gone its been with friends and its offered that little extra sumting with every excursion that took me off the beaten path. I'm not reckless but I do look towards going places and doing something out of the typical tourist box. And each time I go I strive to incorporate something new and different into the trip.
I always punished myself for never straying too far from Negril but I have more of the "bug" to do that now. We'll see how the wind blows me this winter!