I've always tried to find names that were unique and important to me.
My first big boat was TASCO II (Thomas A. Short Co), a Phil Rhodes ocean racer (a terrible cruising boat) which seemed inappropriate for me, so I took her back to her first name, Mistress, which was OK, but not special.
Next I named a Brown Searunner that I sailed a good bit of the way around the world, Haleakala, which means 'house of the sun' in Hawaiian, which seemed pretty apropos for a tropical cruising boat.
I wanted to name this boat Haleakala also, but by 2009 there were dozens of boats named that, so I went with Skipping Stone as there were none listed in any of the registries I searched back then (not so today, by the way). It seemed apropos for this boat, a pretty heavy old girl with a light step on the water.