Advanced Placement

NEXT PARENTS WEEKEND, BOOK A HOTEL OF A HIGHER DEGREE.

- Kate Betts

When Ben Weprin was starting out, working for a real estate firm in Chicago, his boss sent him to see a luxury hotel he was thinking of buying. Weprin showed up one afternoon at the Esperanza in Cabo San Lucas dressed in his just-out-of-college work uniform of a button-down shirt and boat shoes. “I had never been to a luxury hotel before,” he says, laughing at the memory. “There was an infinity pool—I’d never seen one of those—and this lady came up and asked if I’d like a foot massage. I asked, ‘How much?’ When she said it was free, that was it. I was all in.”