Tyler Perry
Who wouldn't treat themselves to an island in the Exumas of the Bahamas for their birthday if they could? That's just what Tyler Perry did in 2009, purchasing White Cay Bay (one of the places you can swim with pigs) and an adjacent island for around $7 million. He's since built Balinese style bungalows and villas on the property, and even learned how to fly a plane so he can escape there whenever he wants. Casual.
[Photo via @lilkiminwi]