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

Fuel is one of the essential considerations when building a boat. Modern catamarans will (for now) all have diesel. It runs your main two...

If you spend some material time in St Lucia, someone will eventually tell you that St Lucia is the only country in the world named after...

I spent a long time in the marketing space. And several years as a strategist. One catchphrase you always hear is, “Great strategy is...

One question I often get is why your boat is registered in the Cayman Islands (C.I.). This is a decision that a new boat owner needs to...

As I continue to make my way slowly north, I realize that the journey is the point, not the destination. I have lots of time to reflect...

As we left Grenada behind sailing north, we stopped at Union Island. One of the things about sailing is that you are constantly checking...

People who own boats have a saying: Getting out of the marina is the hardest step. When your boat is in a marina, there is always one...

I returned to Grenada this week to oversee the final repairs. The list of items needing fixing was over 20, with five or six being...

People in someone's life who would rally for them without a question.   Let me take you back to three and a half years ago.   My brother...

35 days. With leg three over and leg 4 looming, I thought it might be interesting to share some basic facts about the sail. REIMAGINED is...

Grenada has been our leg three loadstar. The last day began about 85nm outside of Grenada. As we rounded Tobago, the northern island of...

We are now within legit striking distance of the end of leg 3. By the time we round into the marina, we will have covered (to be...

Early in the trip, I spoke about being on night watch without a moon. The way this trip unfolded, it began and will end with the new moon...

A tropical depression is spinning in the North Atlantic Ocean. A few days ago, we graduated from the South Atlantic Ocean to the plain...

The last 24 hours have been interesting. After reaching Brazil’s mainland coast, we have been tracking the coast along the continental...

Today, it rained. I know! All day, it was cloudy and rainy. I had this idea that this trip would be epic: sun, big blue skies, and killer...