I'm in the same boat, needing to take the plunge for the first time. I was thinking of Cyprus or Malta in October for a bit of gentle sun before the winter. Difficult to know where to go, but have been to both islands before, so they would be sort of familiar. Never been to Prague, so can't help you there - but good luck if you go. I'm also thinking of going to one of the Discovery Weekends in June to see how I get on