EddTheBrit - We took delivery of two Adventures about 2 weeks before the Island was announced. Of course I temporarily had buyers remorse, wishing I had waited, however, after giving it much thought and inquiring with Hobie about the possibility of upgrading my new Adventures (not an option), I realize I would have made the same choice today.
As a long time sailor, who still loves to sail, I prefer the simplicity of the Adventure over the Island. My wife and I are delighted with our Adventures. Of course, we added the sail kit and dagger board. Having owned and sailed boats ranging from 12-35 feet, I can really appreciate the fact that,with the kayaks, there is virtually no rigging time, no frustration about the lack of wind, or excessive wind. I also enjoy exploring shallow water and shorelines, something that doesn't work well with a sail boat. The Adventure is perfect if you want to primarily kayak and sail when the conditions are right. With more time in my life, I would definatley add a sail boat to the family fleet. For us, Bravo or Getaway would be better much better than two Islands (two would be a handful on the car and getting to the water). The Island is definately a single handed sailing craft.
Of course, we all use our boats differently and I can see why many would be so enthused with the Island for fishing and single handed exploring.
PS We like the white hull too (much cooler in a hot climate).