Sail Around the Caribbean

Even though we were not up to crossing oceans on a sailboat, the cruising life was still appealing. We came up with an alternate plan that sounded very reasonable. We would spend a year or two sailing around the Caribbean. With this approach, we would not have to buy a sailboat that was capable of offshore sailing. We could manage this feat in a sailboat that was designed for only coastal cruising, which would save us a lot of money and would have more comfortable accommodations compared to an equal sized “offshore” sailboat. The Caribbean would offer us easy sailing, beautiful islands, diverse cultures, and of course, frequent hurricanes. Due to these frequent hurricanes, most insurance companies offering boat coverage require boat owners to be outside the “hurricane box” from June 1 to November 30. A full six months! The “hurricane box” is basically the entire Caribbean and the Gulf of Mexico. To be outside this box you would need to head back to the US or go to Venezuela. But even with these limitations, we figured it would be a fun adventure and we could manage it.

If we were to become “real cruisers,” we would need to be better sailors. Since Sydney was a small baby at this time, we did not have a lot of chances to take out our own boat, a 1969 Westerly Centaur that had turned into a major project boat (aka money pit). I had read that one of the best ways to improve your sailing skills is through racing. So, I checked Craigslist and sure enough, someone was looking for crew. I met up with the local Ranger 20 fleet and got a position on a boat for the Thursday evening races. I started racing once a week and quickly built up my sailing skills. But river sailing and offshore sailing are in completely different leagues and I felt I needed to gain offshore experience. So, through a bit of networking, I got offered a crew position on a 36-foot sailboat and did the Swiftsure race out of Victoria, British Columbia, as well as several local races.

I was quickly gaining the skills we needed to go cruising and the only thing we were lacking was our own proper cruising boat. So, we sold our project Westerly and bought a 1988 Pearson 27 sailboat that was to be our family friendly cruising boat. Instead of working on a project boat during our free time, we could be out cruising and gaining additional experience. This was not to be the boat we would cruise on for sailing around the Caribbean, but it was the right sized boat for our local waters and was very comfortable. We named our new boat “Ollie” after one of Sydney’s favorite books about a gosling that did not want to hatch and come out of its shell.

On a warm summer day we were out cruising with friends on our new boat in 12 knot winds. Kerri and Sydney (2 years old at that time) were down in the cabin when the unexpected happened. The aluminum mast bent in half and came crashing down with all of the rigging and sails. Luckily, no one was hurt and after some assistance from nearby boaters, we got the broken mast, sails, and rigging stowed on deck and motored back to our marina. That evening I called our insurance company and made a claim. Insurance would take care of everything, right?

We had purchased the boat from two guys that started a business fixing up boats and reselling them. They had purchased this boat without a mast and purchased a new aluminum mast and boom and assembled it and installed it with all new rigging. But according to the marine surveyor that the insurance company hired, they had assembled it wrong. Our insurance policy stated that they would not cover the cost of damage caused by improperly assembled parts. So, the insurance company screwed us! The boatyard charged us about what we had paid for the full price of the boat to do the repairs. We ended up taking the guys that we bought the boat from to court. We won, but the judge screwed us on the amount of money we received. After spending over a year dealing with insurance companies, boatyards, idiots that did not know how to build a mast, and the court system, I never wanted to see another sailboat ever again! We put the boat up for sale as soon as we got it back from the boatyard and I quit racing. I needed a break.

This experience helped me realized that if something broke while cruising, the costs would be expensive, repairs would always take longer than you would think it would take, and insurance companies will avoid paying any way they can. They say cruising is just fixing your boat in exotic places, and I can easily see that that is probably a good definition. During this time I also realized that the sailing dream was my dream and not necessarily Kerri’s dream. We both wanted to see the world, but not necessarily by cruising on a sailboat. Traveling should be fun and we were not having fun anymore with sailboats. I firmly believe that if your life is full of roadblocks, then maybe you are going the wrong direction. It was time for us to look at other options.


Dreamer. Photographer. Sailing addict. World traveler. I left my desk job in Portland, Oregon to travel the world...

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