If you are a little shy about it at first, just enter or watch one of the activities at the sexy pool and you won't be anymore hahaha
If you are not comfortable going topless don't do it! But if you don't do it you'll be in an extreme minority! Many Americans have such a perverse opinion of toplessness and that's such a shame!
We were a little apprehensive before going our first time in 2010. No idea what to expect. Now, we'll be there every year. Same time because we met such fun people (we'd go more but three kids keep us busy). In the end, do what feels comfortable for you. Truly, no one cares either way.
Just go with the flow When we went early August I would say 40% were topless and 60% were not. I think out of the 14 days we were there I was topless 2-3 days only (and only in the pool). However on the Boobs Cruise I was nude pretty much the entire time lol (and this was day 1 of our vacation). I don't think there is pressure - just go with the flow. Nobody seemed to care of stare like a perv lol!
I should also mention that we went skinny dipping probably 9/14 nights there. So if you don't want to go topless during the day you could always start with the night