Sailing the Eastern Caribbean
Community
Mar 7, 2026
Meet Emma and Andrew Knott
Meet Emma and Andrew Knott and their mini Aussie, Isla. They’re currently sailing the Eastern Caribbean after leaving Key West nearly two years ago to cruise full-time and begin their journey around the world.
Before they met, Andrew was already living on the water aboard a trawler in the Florida Keys, working as a charter captain. Emma, on the other hand, was living in New York City, working in marketing. A month after getting engaged, they found out their landlord was selling their building. With the housing market in Key West out of control, they made a bold decision: instead of finding another place to live, they’d buy a sailboat and eventually take off to explore the world.
Go before you’re ready!
If you wait until everything feels perfect, you might never leave the dock.
Leaving Key West, there was one catch. Emma didn’t really know how to sail. Aside from sailing a Sunfish on a lake growing up, the open ocean was completely new territory. Andrew had years of experience, but this boat was new to both of them. So they learned together while Emma learned how to sail offshore in real time. After a month of exploring the Bahamas, they knew cruising was what they wanted to do full-time. When they returned to Key West, all they could think about was leaving again, this time with no plans of turning back.
One of their biggest lessons?
Open communication. Always.
Living on a boat with your partner demands it. Over time, they found their rhythm, supporting each other by clearly communicating what needs to be done, without adding stress to the moment.
A perfect day on the water for them starts with an overnight sail. Dropping anchor at sunrise. Jumping straight in to check the hook. Then grabbing the speargun and hunting for dinner. Overnight passages were intimidating at first, now they’re their favorite.
The hard days?
They’re part of it. But what keeps them going is the feeling the day after. There’s a calm before the storm and a calm after it, too. That light feeling of relief and accomplishment once you’ve made it through something challenging. They don’t live on a boat for convenience. They live for the challenge. And if they had to choose again?
They’d do this a thousand times over. When they started sailing, they never put a timeline on it. They always said they’d keep going until they no longer loved it. Three years into living aboard. And there’s still no end in sight. Now they’re at a crossroads: east or west to circumnavigate. They chose west, chasing their dream of sailing the remote islands of the Pacific.
