When swimming over a large body of water, my dogs (tamed wolves) try to swim but can't keep up. Normally once I reach land, they teleport to me. But now they don't show up. One time, it had been several minecraft days since I had given up hope of them teleporting and all of a sudden they appeared.
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This is probably normal, intentional behavior. Essentially, any dog (or other mob) that isn't within about 64 blocks of a player becomes suspended until a player gets near again. Whatever it was doing, it just freezes in place, even if it was falling off a cliff. (Suspending distant stuff leaves the game more time to keep stuff around the player updated, which makes it seems more realistic.)
If you cross water, your dogs will start swimming with you, but they may not be able to keep up, especially if you're in a boat or have depth strider boots. If they fall behind, one of several things can happen. Sometimes they may teleport to you, but only if they can find a place near you that's also near solid ground. Sometimes they may turn around and go back because they see a closer path along the shore. But if they can't do either of those, they'll just keep swimming toward you, falling ever farther behind.
If they can't catch up, your dogs will eventually get out of the 64 block range. When that happens, they become suspended and it's no longer possible for them to come to you...until you get closer again, which could be many days later. I think that's what you're seeing.
What you could do to avoid this is change your water route to stay nearer the shoreline and/or follow a course that takes you close to islands where your dogs can teleport near you as you pass. As long as they can stay within 64 blocks, they'll end up with you wherever you go.
Warning: Be careful letting your dogs get into a boat, unless you're already in it. If two of them get in the same boat, there won't be room for you, and it can become a problem getting them out again.