Staying Rent-Free on a Caribbean Island (You Could, Too)

My last 10 years in the workforce involved working and living outside the U.S., and I wanted to continue that traveling into retirement. I’m a man with a permanent place to call home and a wanderlust attitude. How do I satisfy both? Researching the Internet, I discovered housesitting—which has allowed me to live rent free all around the world. It’s simple: In return for free board, I perform some simple tasks for homeowners, ranging from watering the plants to managing some properties…something I did 45 miles off the coast of Nicaragua for three months in 2013.