@jcraig - An outrigger just describes the support floats that are on either side of the boat. They can be put on anything from a pump boat to a kayak or yacht. They basically just add stability so that the boat resists tipping. If you have ever seen any of the Rambo movies, a pump boat is the typical boat with a cloth roof that they take between destinations.
I have been to the Philippines, but I couldn't tell you exactly how far the islands are apart. There are tons of tiny islands that aren't on most maps, and some of those can be less than 10 miles apart. That is definitely a manageable distance for one person. With some of the currents, it would probably be hardly any effort at all.