Remote Year organises world-travel and other recreational activities for remote workers who join their program. It removes the pain of planning the trips while still finding a suitable place to work from. While the pricing might seem costly, it includes stay, travel, workspace, program managers and other events. While some may still like travelling alone, backpacking for 12 months can be stressful if one has to manage everything by oneself.
I like this concept but haven’t tried it yet.