Runkeeper Pro on iOS, together with a Mophie Red for my rides.

Runkeeper because its a great crew of local (Boston) geeks, and it really is a great cross-sport tracker.

But the biggest advantage is using Runkeeper Live to let someone at home dramatically mitigate anxiety by knowing they can (almost) always find out where I am when I ride. In the mountains of western mass there are some data dead spots, but they aren't that large. The funny thing, knowing they *can* find me means they never actually bother to look for me. No more "where are you" texts.

-mr. bill