The issues are the kayak balance point on the cart, and how rough the surface is on which the wheels have to roll. I have a 10-foot sit on top kayak and find that the cart works best about 2 feet from the rear of the boat. That way I can lift from the bow handle and walk easily. Be sure the little legs on the cart are facing forward, if not you'll drag them as you lift and pull. Over any type of rough or soft surface, you must really lash your kayak to the cart securely or it will slide or bounce off. Keeping all this in mind, you should be able to do what you are asking.