Schmap offers nifty guidebook functionality on your desktop (Windows-only) PC. Basically, you install this little freeware app called the Schmap player, and then download guides for the cities you want to visit:
Every Schmap Guide comes with dynamic maps, useful links, playable tours, top picks, plus photos and reviews for 100s of sights and attractions, hotels, restaurants, bars, parks, theaters, galleries, museums…
The map functionality and controls are well-designed, and very intuitive to use. I like that you can easily measure distances, print and email maps, and overlay various businesses and landmarks from any view.
The rest of the UI could be simplified, and I found I got (ironically) a little lost in all the tabs, buttons and maps. The software is in beta, so I'm willing to forgive a certain degree of befuddlement.
Presumably, the Schmap folks' longterm goal is to get the player off the desktop and on to some mobile devices. That's when it would prove really useful. Still, it's innovation in a space–travel guidebooks–that's felt pretty static in recent years.
I first heard about Schmap when they contacted me about using a couple of my photos for their guides (I forget which ones now).