A lot depends on where
the "help" you may need to seek comes from -- or how far away it may from you when you call. I've found that for most coastal cruising situations, a good hand-held VHF, as Ross states, is probably good enough. Some factors to consider would be making sure that your batteries are always up to speed as it takes about 5x more power to transmit than to receive. If you have some way to plug a hand-held into a ship's battery, that is a good alternative. Also, you may want to consider buying something like a Shakespeare emergency antenna (seel link)that you connect the hand-held to and place, by suction cup or other means, as high up as possible. I don't think transmit wattage will be as important as antenna height. I routinely sail the Chesapeake and am never out of sight of land. I use a Uniden hand-held VHF when in the cockpit. While I have a 25-watt Icom in the cabin, with an antenna at the mast head, I've found the 5-watt hand-held has no trouble connecting to whomever I'm calling.