I actually don't think that I have traveled as much as you think. I've only hit two continents so far, for example, though there are clearly more in my future as a traveler. Sounds like you have more experience than I do as a traveler, really.

However, I recently was chatting with the Rian Bornman who runs a quite attractive and informative African travel site called Venues 4 Africa and asked him your question to see what he'd suggest. Here's his answer:

When planning a holiday there are three things that never change. Where do you want to go? What is your budget? Which type of accommodation do you prefer? With this in mind Venues4Africa.com created a QuickSearch to ensure you find what you're looking for quickly.

Our focus is on the Southern Africa region and includes accommodation in South Africa, lodges in Namibia, resorts in Mozambique, safari lodges in Botswana, camps in Namibia and hotels in Zimbabwe. When planning a holiday in Africa from abroad the more adventurous choose to hand pick their own venues and create their own itinerary - guaranteeing themselves a truly African trip dealing with its people and learning first hand about its cultures.

For the less adventurous and perhaps more sensible we would recommend using credible tour operators or emailing our team here in Cape Town for advice on your trip into Africa. And for those who would like a custom made itinerary complete with flights, transfers and all activities and accommodation we can recommend several package deals.

But for those wanting to feel the true pulse of Africa, the roar of a lion at night or the snort of a hippo in the Zambezi, I would recommend you contact us at Venues 4 Africa and tell us WHAT YOU WANT to do and see and then tailor make your very own African holiday.

Sounds pretty exciting to me! Now, there are plenty of different travel information sources for various destinations in Africa in addition to Venues4Africa, of course, and I would definitely encourage you to check out Wikipedia for background information, for example, and then check out the U.S. State Department's Travel Guide to find out about the political situation in a given country before you blunder into what could be a dangerous situation too. But generally, I hope that'll help you get started with your planning, good luck to you, and don't forget to send pictures!