Maggie May is the type of character F. Scott Fitzgerald would create if he were alive today. She comes from the humblest of Kansas beginnings, but “I thought there was something better for me than just conforming,” she says. So she moved to Miami to re-create herself. Signed to an international modeling agency, she appeared in glossy fashion magazines around the world. Along the way she picked up a burning passion for art, architecture and luxurious travel. These days she feels most at home in such exclusive beachy enclaves as the Hamptons, St. Barts, Tulum and the isle of Ibiza. “I know money doesn’t buy happiness,” she says, “but I do like the finer things.” Maggie is drawn to all things oceanic, so we photographed her on a private cruise in a distinctly Gatsbyesque setting—aboard a vintage Chris-Craft on the sun-kissed waters off California. “I think my ancestors were mermaids, because even though I’m from Kansas, I feel totally from the sea,” she says. “I’m a serious sun worshipper, and I hope to end up living on a yacht or sailboat. On a boat there’s a sense of freedom that you can go anywhere, anytime.” Like the Chris-Craft, Maggie is a classic beauty. Her poise and radiance paid off in front of the camera, especially after a glass of fine wine loosened her up. “I found it liberating to be just like, Fuck it and get naked,” says our August Playmate. “I totally admire girls who are like that.” So do we.