@Wanderlusting89
Oh wow that’s so good to hear!!
I can’t help but wonder what I’ll “do” all day though. Maybe that’s because I’ve spent aimless days in Norfolk on holiday this last few years 
Did your days feel full and adventurous?
And where would you go if you were to go now from May!?!
I never had one aimless day. Partially because I was most definitely travelling rather than on holiday.
On my first trip I bought a ‘Round the World’ ticket and used that to travel from one country to another. So Heathrow to Singapore, stop over, Singapore to Brisbane, hire a car and drive, up the East Coast taking in the Barrier Reef, then down to Sydney. An internal flight took me to Uluru, another further South. I flew Sydney to Wellington, another hire car and travelled the whole South and North Island NZ, before flying out of Aukland to Raratonga (hired motorbike rather than car) Internal flight to Atutaki. Then Tahiti, Bora Bora. In to Vancouver, up through Vancouver Island and a passenger ferry to Alaska. Down through the Rockies and California, over to Death Valley and then a flight home from Vegas.
On other occasions, much more time in Canada and the US. Months one summer travelling in a little convertible through Europe etc.
Never once did I book accommodation more than a day ahead, apart from the first and last nights in Aus and NZ.
Only once did I feel really at risk in terms of where I stayed, although there were times when I questioned my choices.
If leaving in May I would be furiously researching now, planning a rough route (try not to tie yourself down as there will be places you will want to linger) and identifying accommodation resources. My initial trip was before the days of real connectivity, so guide books and accommodation guides were essential. Also understand where you will be safe and where you are more at risk.
Follow the sun where possible (within your own temperature tolerances), take 1/4 of the clothes you think you will need and make sure you have a good medical kit. I never once failed to purchase new clothes, but medication was another matter.