Place Your Kayak At A 45 Angle
With the bow well behind your vehicle so you can lift it and place it on the rack from the side. Lift the stern and push forward. Then swing it around. That’s how I load my 16’ Tarpon. I run my strap through the scruppers. It won’t slide forward or back that way. No need for lines running from the bow or stern down to the the vehicle.
Best Suggestion Yet
And exactly how I get those big heavy plastic fantastics on top of any available car.
But better yet is to get a lighter canoe or kayak. Right now, I’ve loaded a 26 pound, 21 ft. long and 17 inch wide surfski on top of a tall 4Runner. At 26 pounds, it was easy to hoist overhead and rest the surfski on two portable gray foam blocks (available at kayak shops) on the roof. The surfski is secured by two cam straps (looped) up front and one cam strap (looped)in the rear. I carry the foam blocks and straps in my check-in luggage wherever I travel. With this method, I can easily get on the I-76 at 70mph and cruize at 60 on my way to Marsh Creek State Park for a work out, when the rain stops.
meopilite’s method
So if you are loading/leaning your kayak on the rear of any newer SUV - aren’t you actually leaning the kayak on the rear windshield housing thingy? Some of them stick out quite a ways and seem too flimsy for that. Others are smaller and probably ok. Seems all new hatchbacks and SUV’s now have the rear windshield wiper in these housings at the top of the roof/rear window. I think this is problem for rear loading. Is the Grand Cherokee’s one of the smaller ones that don’t stick out as much?