Liveaboard Scenarios for Canadians in the Caribbean

Hello all,
Please accept my apologies if this has been addressed, but I have done lots of searching and have yet to find the information that I am looking for. It is very broad, yet specific to Canadian citizens. Some of you reading this might roll your eyes as you read this, and I am sorry for that. I have minimal saltwater experience (three Gulf Stream crossings, on a small boat not a yacht, from Florida to the Bahamas), and if I can find a scenario that works for me, appropriate training and education would be part of my personal project plan.


Background: My wife and I are Canadian citizens, and I am looking ahead to an empty-nester retirement scenario where we keep our primary residence in Canada, but live aboard a 44-60 foot power cat during the colder months (maximum 6 months). If you have Canadian-specific knowledge/experience, I would appreciate it if you would share it. I am not looking for guidance on which yacht would be best to purchase; however, if you would like to share this information, it would only make this thread more interesting. Maybe this thread can grow to the point that future Canadian dreamers can find most of their questions answered in one thread.

Timeline: Live aboard for a maximum of 6 months per year for at least 3 years. I am thinking that this scenario would fit nicely between selling our current big house and transitioning to a smaller empty-nester house.

Region to explore: Caribbean, mostly on-grid. I am open to the idea of storing the yacht on land in Florida, and moving it into the Caribbean for part of or all of the liveaboard months. I am also open to the idea of keeping it in the Caribbean year-round. At this time, I am not considering changing citizenship due to Canadian departure taxes, restrictions linked to travelling back to Canada to visit family, and being cut off from the Canadian healthcare system which we have paid into for all of our working lives. That being said, if someone has personal experience working through these issues via a citizenship/residency change, I would be interested in learning about it.

Any scenarios that you would like to share (specific to Canadians) would be appreciated. Some areas of interest are (but not limited to):

1. In what country would it be best to purchase the yacht in? I would like to minimize taxation, and registration costs.

2. Weather. I am not a fan of hurricanes and tropical storms while living aboard (kind of obvious), and I would want to have a land-based storage solution that can mitigate the effects of extreme weather.

3. Infrastructure/Services: Access to maintenance/repair of the yacht. Access to medical services. Access to restaurants, food, and supplies.

4. Proximity to exploring islands/regions that are known to be reasonably safe.

5. Insurance is a concern. If you share a scenario, please include your insurance solution.

6. Docking, mooring, and dry-land storage costs linked to the scenario.

7... Feel free to add important topics that I have missed.


Don’t worry, I will not be insulted if your contribution to this thread starts with “Oh boy, you have lots to learn. You’re not even scratching the surface.” Please just don’t call me an idiot for thinking ahead.

I am trying to understand the scope of this possible retirement scenario, and start to dive into the areas that could make it a reality.

Ideally, your contribution to this thread would start with “I’m a Canadian citizen, and this is what I did (or I am doing)”, or “I was a Canadian citizen, and this is what I did (or I am doing).”, or “This is what I did, and it got me divorced. :[ “

Lastly, if this is not the appropriate forum to post this in, or if there is a better forum in which to seek this type of information, please feel free to let me know.

Thank you,
Moose