I regularly spent time in Florida mostly in the Jenson Beach to Palm Beach area. A couple of friends lived there, and I would visit frequently. But for some reason I have a block against Florida. It was a fun place to visit, but nothing ever said to me come live here. Honestly I don't know why.
Growing up my parents had a place in Pompano Beach and as my wife and I got older we realized we are not big fans of the East coast of Florida. My wife was born in Pensacola and lived the first 10 years of her life in the panhandle, has a bunch of Florida relatives and has vacationed all over Florida each year since the 70s.
After we got married we searched for a retirement spot by vacationing all over Hawaii, California, coastal Florida, and Mexico. We fell in love with Naples about a decade ago as the best compromise as Hawaii and Mexico have pros and cons as well(CA is mostly cons, lol). It has a lot of the things we love including the ocean, boating, golf and the sunniest and warmest winters outside of Hawaii. Key West and Miami are about 0.5 degrees warmer in the winter but we like Naples better. My wife's mom also lives there and some of our very best long time friends have a condo 100 yards from ours in the same complex. Another couple that is also in our tight circle of friends going back to the 1980s is closing on a condo just 0.5 miles north of ours on May 8th.
It will be fun to have great friends close by in retirement and believe it or not, all three of us belong to the same CC in Minnesota so it will be year-round golf together us just as soon as we can get our high school kids out of the house! For all of us that happens in the next few years and in the meantime, all three of our families will enjoy Christmas and lots of other Naples vacations together escaping the MN winters.