I know two guys that have kayaks on top of their cars. One of them goes locally to Lake Okahumpka State Park, it's the big lake between 44 and the Turnpike. With all cart paths in the new area, it may be golf cart accessible or will be probably someday.
Lake Okahumpka Park | Sumter County, FL - Official Website
The other fellow is my neighbor that I play with for the past ten years. He likes going out of town. Next week he's going to Key Largo in the Florida Keys for the third time in past six months. He normally goes to Venice, which is below Sarasota and above Fort Myers. He'll go all over the Gulf Coast, sometimes he'll surf fish, they went to Destin a couple of months ago.