There is never a perfect time in life to travel, but don't keep putting it off only to find out that you wish you had taken the plunge sooner. There is no doubt that it was easier to travel when I was younger, especially going the dirtbag / youth hostel route, but travel is incredibly refreshing, if only to make coming home feel new and wonderful.
Once you get going, you'll be amazed at how easy and fun it is. I'm definitely sensing an inertia / over-thinking issue, since, you know, I'm a professional psychiatrist and all :)
The idea of the Mediterranean Cruise is a good one - you get to see several cities (ours went to Malta, Pompeii, Rome, Florence / Pisa, a couple places on the French Riviera, and Barcelona) - but hardly have to do any planning or work, other than having clothes and toiletries. You can be as adventurous or lazy as you want, but maybe hold off on the African Safari for now...