Start a Boutique Hotel

While this is incredibly hard work, this has two major benefits: one, your office is the Caribbean, and two, you’ll be providing employment for locals — meaning you won’t just be spending a “retirement” — you’ll be helping the local economy. And there are loads of hotels currently on the block in the Caribbean, particularly small boutique properties, particularly on islands like Puerto Rico and in the Dominican Republic. For a place full of smaller, more affordable lots, try Dominica, the “Nature Island,” with dozens of tucked-away properties perfect for a “starter” hotel, like the one above, which is currently on the market. On a smaller scale, you can even turn your home into a bed-and-breakfast, opening up the options to more islands across the region.