Obviously I'm a fan of Google and therefore Google Maps. If you've seen my blog WhereIveBen you'll also see that I use Windows Live Local.
One mapping capability that I hadn't found was the ability to set specific waypoints along the way thereby sending the route along something other than the shortest/quickest route.
I had found Harley-Davidson's Ride Planner but that was really hard to use as you had to give it a specific street address for every waypoint (or at least that was the only way that I could find).
Then last week I came across a blog entry talking about ask.com's maps. The part talking about maps is some ways down in the entry.
I played with it yesterday and I like it! To set a waypoint, you just right click on the map and it locates the closest reference point. It could be a street address (like Harley's Ride Planner) or it could be an intersection (which is just what I wanted). You can also just drag a waypoint to wherever you want it.
I used it to lay out a motorcycle ride and here it is. Yeah, it's not a tinyurl but it works.ask.com's maps has satellite imagery and even a topological view but doesn't seem to have any maps outside North America.
Another time I'll tell you about ask.com's blog search and why it's different.