"Saint Pete's" presumably refers to Saint Petersburg, which is the fifth most populous city in Florida and the second largest in the Tampa Bay area (after Tampa itself). Its population was 257,083 in 2015.
The St. Petersburg in Missouri, home of Tom Sawyer and Huckleberry Finn, doesn't exist in real life.
Clearwater is the smallest of the three principal cities in the Tampa Bay Area – population 107,685 in 2010.
Naples (population 20,600 in 2015) is one of the USA's wealthiest cities, with its sixth–highest income per capita and the second–highest proportion of millionaires per capita.
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