You can pick where you want to go or when you want to go—but often not both. Sailors pretty commonly use this saying. The truth is, there are a lot of times when you get to pick neither. Winds and waves kept REIMAGINED around Antigua for almost a month. But when a small window finally opened, the destination was clear. Montserrat. It was (and still is) a British Overseas Territory—similar in status to St Helena. Just 27 nm from the west coast of Antigua sits Montserrat, an is

I’m in Antigua. Been here a little while. Waiting on a weather window to sail away. It’s well understood in sailing that the boat can often handle more than the crew can. And so to avoid confusion, I have a set of wind and wave parameters I like to sail in. I’m in no rush. The other day, I overheard two people talking about the weather and leaving. One said, “You need to be more aggressive and just go.” And I immediately had a flashback. For years, in boardrooms and offices,

I’ve spent a fair amount of time travelling and talking with people about travel. I have noticed one of the places people love to go — and love to talk about going — is the South of France. From Nice to Marseille, there are a ton of small towns where people vacation. And of course, the big names like Cannes or Saint-Tropez. People go because the water is warm. The beaches are… fine. But mostly, people go because they want to say they’ve been to the South of France. Don’t get

Sometimes we find ourselves stuck in the middle — between two opinions, two extremes, or two possible paths forward. Most of us have been there. And sometimes those situations overlap in ways we don't immediately recognize. For me, Dominica represents what it means to be stuck in the middle. Five years ago, I couldn't have picked Dominica out on a map. I knew it was somewhere in the Caribbean — and that was about it. Sailing north, REIMAGINED stopped in the northern part of t

This year, I spent a fair amount of time exploring the Grenadines. For people who are aware of the Grenadines, it is often known as a place where the very rich and famous hang out. Mustique, long known for celebs and royals. Up-and-coming Canouan battling to steal some of Mustique's mystique. And of course Tobago Key. Often cited as a must-go for snorkeling and diving. All wrapped up in a season of Below Deck filmed in this area last year. They are hard islands to get to unle

There is a process with boats. Most boats in the Caribbean seek shelter for hurricane season. Most of the time, this involves putting your boat on land, on stands in a boatyard. The yard I kept REIMAGINED at last year had over 400 boats. The prep process for it is interesting. On the way out, called decommissioning —your mission is to clean the boat, remove everything, take systems apart (like fresh water wash the air conditioners), wipe things down, and store everything. It

About five months ago, REIMAGINED came out of the water for hurricane season. She spent the summer sitting in the yard on some sketchy-looking, homemade stands that somehow did the job. It was my first time captaining a 53-foot catamaran — 17.5 tons of fibreglass — into a tight little dock to have her hauled out. Let’s say, it was a moment. As I looked back on last year, I realized my sailing season was a mix of wins and wipeouts. Plenty of lessons. I managed my way through i