We don't always enter the water that way at all. It all comes down to what is convenient. In a small craft, that has no deck and it's freeboard is close to the water surface, sure, we'll roll off backwards because we're already sitting at the gunwale of the boat...maybe even sideways depending on how we have our gear rigged.
It's difficult to do a giant stride off a boat that has no deck. We will also use this method if the water is shallow, like off a jetty. We don't sink very far when we hit and we have a place to sit and roll off sideways.
If the boat is larger, has a deck, the water deep enough for the fall and the freeboard is less than 8 feet or so, we will do a giant stride entry because it's easier to do when you're already standing. Difficult to sit on a deck and roll off backwards. Not many can stretch like that besides the fact you have to crawl on your hands and knees to get there.
Why do that? A giant stride is just as the name implies. We take a large stride off the ... more.
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