An Egregiously Planned Route?

[Gin-N-Sonic]

Okay,

A little about me, I've been spoiled, I'm a motoryacht guy, managed one, spent time on others, etc, then I saw the Moonbeam of Fife III in action, in person, completely lost my *beep*. Standard thing for me was get to Miami, meet up with the boat, motor south. As you can see, there's a swath of ocean between Canada and Bermuda that I haven't toyed with. Bermuda yes, but approached from south.

Now I have a family at hand that is insane enough to consecrate their time to not just learn sailing but also put aside a year to cruise. My son has actually ceased playing his Playstation and taken up reading sailing and navigation books.

My business is easily mobile and sustainable to support this trip and we will most likely end up with something like a 50-ish foot catamaran. My son is 6'6" at 16, he needs his headspace.

Hence, without further ado, here is the route we are thinking:

Toronto to Montreal, onwards to Québec, maybe Gaspé, then St. Piérre and Miquelon and then, either the coast hugging thing or do a run for Bermuda? From Florida, we plan to do Berries, Exumas, Turks and Caicos, BVI, USVI, PR if everything is safe, Curaçao, then off to Panama (Shelter Bay), across to Hawai'i, then French Polynesia, Easter Island, Panama, back to Curaçao and follow the same path home to Toronto. Your thoughts please.

We will be hiring or boarding an experienced Skipper or Captain that we can learn from.

We're looking at a possible September departure time frame to get further south before early winter while avoiding the fun Hurricane season. Trip is in two years and the expected length of time will be 1 year.

With so much of a sailboat operating at the whims of weather, I can easily see that the planning needs to be grilled, picked apart and redone as necessary, please feel free to pick it apart and offer any advice.

I should point out that I have not vacationed as much as of late, and I do understand a lot has changed out there, so any input would be most valuable.

And attack!