First, this amusing item that I blogged right away, before editing the post to add the rest: The Prejudice Map shows a map of the world with callouts identifying stereotypes gathered by Googling "X is known for" where X is a nationality or cultural group.
Some hilarious juxtapositions appear, like Turkey's tags: "Hospitality. Using weapons." It's unscientific, but as a travel map it isn't completely useless. For instance, it makes me want to go to Cuba: "relaxed, humor, sophisticated jazz." On the other hand, you have to admit that the UK sounds pretty bad unless you like dirty but posh restaurants with nice management: "fair play, aristocratic kitchens, extemely unclean, rarely complaining."
Then, there's the now ubiquitously blogged Starbucks Center of Gravity in Manhattan map, which I include just in case anyone living in Manhattan cares to know where all the neighborhood coffee shops went in their neck of the woods. Apparently there was also once a Starbucks Avoidance map, but the link is broken.
Try the Avenza Publisher Map Awards, which are all maps produced in Adobe Illustrator using GIS support. Winners available in PDF and jpg. Good news for any Seattle readers, the Grand Prize winner is a geologic map of WA state, and a runner up is a hiking map of King county. How they were made is described, which is very cool. As is this quote from Van Gogh they stuck on top: "Great things are not done by impulse, but by a series of small things brought together." But in the "you've got to be kidding me" category, there's the interactive map of Bethesda, MD. I grew up near there, Bethesda is not interactive.
A map of the world showing dots corresponding to newspapers, from newseum, and when you roll over the dot, you get a thumbnail of the front page. It expands to mostly readable. Quite useful, actually.
Seemyroad is filming towns, and has Zurich down pat. Zoomable overhead map, plus. You can get ride-throughs of locales, reminiscent of the Paris ferrari's bumper video, except not so illegal. (They stop for pedestrians and red lights.) You can also get a tramline fly-over from the sky. I'd really enjoy this for London and Paris.