For me the question would be what do you wantout of the trip/journey?
It sounds obvious but many people set off only to discover that continuously moving ALL the time can be mentally as well as physically tiring.
How much time do you like to spend on your own,a week,a month?We all need human contact so this could dictact your location,or even a STYLE of travel,for instance, hitch-hiking will put you in to a more flying-by-the-seat-of-your-pants-mode ,where as continually slogging on foot for weeks in the wilderness means a more structured,methodical approach IMO,i guess what i'm trying to say is we all have different mindsets and if you have a rough idea before you set out it can help(save you money and time!).
The WOOFing thing is a great idea,i have done this on my travels(Canada & Tasmania),made life long friends,but also its a refuge from the rigours of the road.It seems to me on alot of the "ultralight forums" alot of people take great pleasure in getting from A-B as quick as possible,.Sorry i don't get it!Lighter yes,but not necessarily faster......i would just love to hear someone who walked the Appalachian Trail....but took them 3 YEARS instead of 3 months!!!!!!
For me personally i would want to go and expierience a "New culture",different people,ideas but somewhere with lots of space still.Latin America comes to mind,Patagonia,the Andes,Amazon,Atacama dessert....you can always find somewhere warm too.Great people too.....when they're not shooting at you.I would NOT be taking any expensive gear with you too!
Make a date and just go...!!