Ha! I love it. I can just see the two of you paddling around.
I assume what you want to do is get in some light recreation, paddling around lakes and ponds. Not running whitewater, or trying to tour from island to island in the ocean. With that in mind, Id almost certainly go with a sit-on-top. Otherwise I have no idea how youd get the lab into the cockpit. One candidate would be the Wilderness Systems Tarpon 130T ($800; wildernesssystems.com), a really nice boat that has excellent stability, plenty of storage for beer and dog biscuits, and a sturdy rotomolded hull. Youd have to work out where you sit: front or back (back is my guess). Ocean Kayaks Sidekick ($650; oceansidekick.com) would also work well.
Labs love to participate in any activity, whether riding in a pickup or hiking a trail, so I think your hound will catch on pretty quickly. Id certainly take some time to work with the dog on dry land, setting the kayak on the ground then encouraging the dog to sit in the correct position. You should sit there, too. Make sure the dog associates one of the storage areas with treats of some sort, to expedite getting him back into the kayak when needed. And certainly get a flotation device for the dog. The Fido Float ($38 in extra large; fidofleece.com) comes in orange or yellow and has handy grab handles for hoisting the dog into the boat.
Next, find a VERY quiet body of water, shallow and close to shore, and practice. Make it fun for everyonelots of treats and petting when the dog is in the boat or returns to the boat after a swim. Work on the loading system when on the water; maybe your dog will figure out how to clamber into the boat on his own, which would be ideal. Once all that seems to be worked out, then try a trip. And send us a picture!
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