I decided if I was going to be comfortable my with my first experience as a nudist I would start by doing something I love and am comfortable doing. Jan 2009 I enter a Tennis Tournament at Cypress Cove Nudist Resort near Orlando Fl. I had a unbelievably terrific time.
I think the best way to start is by choosing an activity you enjoy, and finding out where people do it naked. Otherwise you may find yourself sitting by the pool alone being naked but bored.
My wife tried but didn't really "get" nudism - sitting around doing next to nothing - until one day when we decided to attent an annual resort "Olympic" event. There were several activities organized. And the next thing I knew my wife took off running around the pool to take part in it. She had a blast. Nudist activities was her thing.