How to plan a round-the-world trip

You wouldn't tease a girl, would you?

How to plan a round-the-world trip via CNN

In the days of the Victorians, a tour of Europe for a month was a standard honeymoon. Now, unless you have a considerable fortune and lots of time off, the only time you can go a multi-country trip is a financial-aid funded study abroad program, or a gap year. 

I've been wanting to travel around a la Daisy Miller since I first picked up Henry James. A young girl seeing the world, a chaperone, and a native tour guide from a beautiful hotel...yellow fever need not apply. 

It's not Travel Tuesday, but we all know the important questions isn't "Where do I want to go?". It's "When am I going to do it?".

Another question would also be, "What if you go below the equator?".  
Does that count as left to right?

I do get jealous of rich kids who were able to do a lot of traveling before they graduated college. In my opinion, your twenties are the best time to do it, while you still have the strength and ability to cover the miles on foot; as well as the availability before jobs and kids and obligation. 

The CNN article has some great tips on circumnavigation (yeah, Magellan). It will require a lot of prior planning and a travel buddy just as flexible as you are. Keep to your itineraries and don't go changing on a whim.  

If you have gone on an around-the-world trip, what do you suggest? 

I promise I won't be repugnant...at least I can pack light.