On the swimming front the biggest issue will be getting him back in the boat. A wet lab will be too heavy to lift. Our lab loved the pool and we taught him to use the ladder, you should try that with your swim ladder. You may want to try it when you have a back-up path available, like a beach and a dock.
Another issue is where will he do his business. If your talking short trips he can hold it. But if your out all day you're going to need a plan. I've seen people bring there dogs onto private land near sandbars, but I'm sure the landowners would not be happy. Some of the public docks have nearby areas.
Finally, watch how tired he gets. Dogs don't plan very well. They don't make sure they have enough energy to get back from where ever they go. That's why some people but life jackets on dogs, even swimming breeds.
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