I'm a first timer and was looking at taking an awesome first holiday with JY holidays too. Wasn't sure which to take but for me, it's looking to be either Peru or South Africa. Peru has got Machu Picchu, one of the New Seven Wonders of the World. That would be pretty sweet to see. Or Africa, going to Swaziland and riding some elephants in between chilling at national parks. Your spoilt for choice really.
Was there a particular area you wanted to do? Asia? USA?
As for a taster weekend, I suppose somewhere close to the UK would be good. Maybe France or Germany? Or really close would be one they do to Belfast and Dublin.
I'm new to travelling single too and am a little nervous, but you only live once so I'm just gonna go for it! There will be plenty of other travellers whom are most likely going it first time by themselves too.
Hope you make up your mind soon fella! Take it easy!