My first and only parasailing experience was when I was at my heaviest, which was about 285 pounds. Definitely Pooh sized. I've also been very nervous about heights, but not petrified. I love to fly, and I enjoy going up to high places and looking "out" at the view, but looking down always gives me chills and a tingly feeling in the back of my legs. That being said, I also booked parasailing because it's just something I've always wanted to do. So I did it. Just like someone posted above, the instructor keeps you so preoccupied with all the small talk that you hardly have a chance to be scared. I went in tandem with a friend that was only about a hundred pounds, and we were side by side. You would have thought we weighed the same...the contraption didn't tilt to one side like I feared it might, and I fit in the harness just fine. We didn't have much instruction about how to "hold on" so I ended up gripping the bars pretty tightly, but I didn't need to. The harness definitely holds you up. Once I was up there and looked down, I felt a little nervous, but then I just told myself to go for it, and enjoy the ride. I loved every minute of it and was very disappointed when it was over. I'm planning on going again at Castaway Cay on our summer cruise.