While you’re not likely to run into any Hollywood royalty on your St. Augustine tour, that doesn’t mean the rich and famous never show up there. In fact, there have been several celebrities and famous historical figures who have lived in the Ancient City at one time or another. Florida residents will likely recognize Henry Flagler, a well-known industrialist with ties to St. Augustine.
Flagler is most famous for founding Standard Oil, building the Overseas Railway to connect the Florida Keys to the mainland, and helping to found the cities of Palm Beach and Miami. Henry Flagler kept a mansion in St. Augustine, although it was demolished in the 1950s.
If turn-of-the-century industrialists aren’t the type of celebrity you’re looking for, perhaps a music legend is more your speed. St. Augustine was once home to a young Ray Charles, who attended the Florida School for the Deaf and the Blind in the city for eight years. Although he would achieve his greatest success living and working in Los Angeles, Charles got his start in the northern Florida music scene, playing clubs in St. Augustine and nearby Jacksonville.
Alright, so Ray Charles did pass away in 2004 and the title of this blog did promise a celebrity who lives in St. Augustine – present tense. We’ve still got you covered though, because two St. Augustine houses were sold in 2023 to the one and only Vanilla Ice, who plans on flipping one and keeping the other. That’s right, the renowned rapper, movie star, and HGTV host keeps a house right here in the Ancient City, just off Highway A1A, so make sure you keep your camera with you just in case you spot him in the wild.
To make the most of your next trip to Florida, check out our St. Augustine Self-Guided Walking Tour, or you can sign up for Action+ and gain access to over 100 tours for a single price.
