Our first year, I was like your wife with no plan on ever, ever being topless! After the first day, I never wore a top! We did go on the boobs cruise in our first year early on and that helped me to be comfortable topless. However, some boobs cruises are a little wilder than just being topless, depending on the group attending... While last minute availability in April May be unlikely (from reading other posts), I would do some more research here about the boobs cruise, with your wife... to see if both of you are comfortable with what you may or not see, in addition to the topless aspect.