The Gilded Age

One thing about those robber barons: they knew how to entertain. And build. And luxuriate. Henry Flagler, seemingly founder of just about everything in St. Augustine, made his money in Standard Oil (as Rockefeller's partner), and he spent a whole lot of it here.

Never one to do things by halves, he built a grand hotel you could only stay at if you stayed the whole winter and paid cash up front (something shy of a half mil in today's money). He wrote a blank check to a pair of 20-something architects and told them to go crazy. They did.

He had Edison put in the electricity. Tiffany did the dining room windows.

Flagler didn't like the taste of the local water, so he piped it in from seven miles away and stored it in fake bell towers.

St. Augustine wasn't a tourist town then, and his guests got bored. So his architects designed another hotel across the street that was basically a rec center: a massive swimming pool in a 3-story central atrium, steam baths, gym, ballroom, beauty parlor, etc.

But wait, there's more! Later on, older and sadder after losing a couple of wives and a daughter, he built a memorial church. 

You can see the tops of these buildings from way out in the harbor; with one other building, they are pretty much the whole of St. Augustine's skyline. For better or worse, this tycoon was probably the founder of St. A's tourist industry.