Hi,I am currently riding my TTR250 named Shiva to Japan. I have already done the first 1000 miles on it and currently is in Sintra, Portugal.
This information from this site was really helpful when I was prepping the bike for the trip. Though to be honest TTR250 is so good that it doesn't require much preparations ;)
After visiting Cabo da Roca I am heading East and currently in Sevilla. Enjoying sun and 25C.
Happy to report that everything that I packed stayed in place. I might replace some things (like sleeping bag and mat) with more lightweight alternatives to make packing easier.
For the nights I am either wild camping or staying in guest houses.
I think I am not as prepared as the bike but riding a lightweight bike helps a lot especially when I need to find a place to camp.
I am not using highways and should say that most of the roads I took in Portugal and Spain were really amazing with lots of beatiful views.
Great adventure mate, hope you reach your goal without too much hassle. How much time have you given yourself for the trip and are you doing a return journey?