Haven't finished one of these in a while, eh?
This one was, in principle, pretty simple. I brainstormed all my favorite literary and onscreen wanderers and put them on some visually evocative cliffs.
From left to right, starting at the top in a U-shape, we have: Jack Sparrow and the Tenth Doctor (Out of the few Doctors I'm familiar with, Ten seemed to be the one who had the greatest urge to just keep traveling). Below them we have Captain Kirk of the Enterprise, Captain Malcolm Reynolds of the Serenity, and Luke Skywalker. (I had initially picked Han Solo, but changed my mind based on the fact that although Han was a seasoned traveler, Luke was the one who really had that primal urge to go out and SEE things).
Up the right side we have two unknown kender, one of whom is a small child with a blank book. Kender are absolutely the first people to pop in my head when I hear the word "wanderlust", so there are quite a few here. Standing with his lute is Kvothe from The Name of the Wind, which I'm still irritated at myself for accidently leaving out of Storytime. But maybe he fits better here. Next to him is Tasslehoff Burrfoot, perhaps the most iconic kender that ever lived besides Uncle Trapspinger himself. Above them we have another kender (who may or may not be Uncle Trapspringer), and of course Scrooge. (In the drawing guide I made for myself, I had Merida there instead. But given who wrote the song...it needed to be Scrooge in that spot). Up by the sign is Aragorn.
There are also four iconic spaceships: the Enterprise, the Millennium Falcon, the Serenity, and the Doctor's Tardis. All explorer ships in different ways. The sailing ship in the fog is meant to be the Black Pearl. The mountain in the distance is the Lonely Mountain, guarded by Smaug.