These newspaper ads ran often in Palm Beach, back in the 1960s and early 1970s, usually around Christmas time, hyping events at Sears where, in addition to holiday sales and free donuts, kids got the opportunity to see in person their "favorite TV personalities". Apparently back then, that meant a bunch of old guys in hats. (I coulda been a contender!)
At first I lacked the necessary suspension of disbelief to even consider that a kid in 1968 would call these guys their favorite TV personalities, but remained fascinated by these grainy old newsprint images of crusty sailors. A quick glance at the googles and we find that sure enough, Skipper Chuck hosted a very popular children's show called Popeye's Playhouse in South Florida from 1957 to 1979. The "Uncle Don" shown in the ad is also from Skipper Chuck's show, according to Wikipedia:
"Skipper Chuck's first musical sidekick who played the Hammond Organ and wore loud Hawaiian shirts....he also served as a straight comic foil for Skipper Chuck's often droll jokes. Don Sebastian Pesce was a local musician who played at local supper clubs in South Florida for years. Don was responsible, with Chuck and Annie, for many of the original songs written for the show."
Additionally, Captain Jack also had a well-loved kids show in Florida, with Banjo Billy (who had his own show, Banjo Billy's Funboat) and Jumpin' Jack O'Brien, from 1961 to 1969. I'd hoped to find some actual footage of these shows on youtube but all I could located was this news piece with a montage of old photos.