Why would anyone sail the oceans by themselves? It’s complicated.

The Chesapeake Bay has no rich culture of solo sailing. Sure, there are exceptions. But it’s a body of water where it’s easy to run aground, easy to go for a yacht club race and easy to party with friends on a day sail. “I know people who have sailed their whole lives and have never gone south of Solomons Island,” said Matt Rutherford, an Annapolis sailor and explorer who was the first to sail solo around the Americas in 2012.