Single- width driveway? If it's double-width you can probably manage to back the trailer in, with practice. I got a _lot_ better at trailer backing after I got some neighbors who park a line of dead cars along the street across from my driveway. ;o) My street is probably about 24' wide (residential street with room for three cars abreast -- two parked and one driving down the middle), then subtract the width of the cars, and Lazy Jack on her trailer is about 21', so similar mathematics to your situation. Same length pickup. Aiming for a 10' wide shelter opening about 8' in from the street. My driveway cutout is only single-width, but the driveway is double-width. I just back over the curb on that side. Somebody's suggestion to try a front-mounted hitch would make moving the trailer around much easier, and probably even make getting it in and out of the driveway doable with a single-width driveway.

I think using a winch or capstan would be a hassle if you're gonna keep the boat at home. OK if you're only bringing it home for the winter.

A fellow I know offered to GIVE me a fancy electric powered trailer dolly because it didn't have the power to get his 15' catboat up a slight slope in his driveway, so be careful if you shop for one. I'd love to have something like that for shuffling my trailers around, but his review made me leery of them for use on anything but flat, paved surfaces, of which I have few. I didn't take him up.

Good luck.

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