I decided for certain that I was going to go forward with the trip about four months prior to the departure date. I had a general looping route in mind which allowed me to increase the likelihood of being in decent weather (i.e. avoid winter and having to carry bulky clothes and rainy seasons) for most of the time I was traveling. I knew I wanted to start in South Africa, so I booked a one-way flight there from D.C. I did lots of reading, obtained travel visas in advance if I could, obtained the aforementioned vaccinations, set up a blog, organized finances, selected backpack etc. I "worked" fairly hard in advance to try to minimize potential problems I might encounter once on the road.
Essentially, this is how I handled the travel itself.....for the month or so in front of me, I generally had accommodations and transit booked. For the month beyond that, I would be doing reading or booking tours, etc and for the month beyond that (3 months in the future) I was doing some very light planning. Then as time progressed I would just bump up the focus and detail for "Months 2 and 3" and add new spots for the following month. I just kept filling in the schedule ahead.
It was probably 50% dumb luck and 50% good planning, but I encountered almost no problems....no missed flights, no robberies/assaults, no incarcerations, no maladies beyond an infected cut while on Vanuatu. I did have my AMEX card get compromised during the same period as my ATM card expired. Getting the replacement cards sent out to me as I was hopping from one South Pacific island to the next proved tricky though.
