I'd go with the buggy, something simple and easy to disconnect and stick behind the house when not in use or that you can chain to a tree or something at the beginning of a trail. Then, you can tote your canoe/kayak up on top of the CJ and set it on top of the w/s frame and roll bar. a couple pads and ratchet straps and you are along your way to the water... Safer I'd imagine than having the side-to-side wind tipping you over going down the highway.

Good luck

91 Jeep Wrangler YJ, carpet, tires, trailer hitch. yea....