Been living aboard my Pearson 365 for 3 1/2 years. Been cruising the Bahamas since Christmas.
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I've been trying. I was weeks from leaving about 18 months ago when an elderly relative got sick and being the only family in the area, the responsibility has fallen to me. I've almost burned through my entire kitty living in an expensive area. I did not plan for this.
Enjoy your trip! I've heard Columbia is nice. I have been to Panama and really liked the country/people, but I have read several reports of cruisers getting robbed around the canal area. Be safe.
Since May this year. Currently on Porto Santo / Madeira. Heading to Canary Islands in October.
First year living aboard my 33ft CS on Lake Ontario and I'm currently getting ready for cold weather sailing. I do have a winter slip but I'd rather be anchoring until the water freezes.
You have to document or share how that's going for you somehow. This is an incredibly interesting subject. I haven't read very much so far about winter sailboat life "out East", mostly from people on the West coast like Vancouver / Seattle area. Other sailors from the North-East I know simply fly out South for the winter.
There's a surprisingly large year long liveaboard community on Lake Ontario. I'd say that there's around 10 marinas or clubs with between 5 and 30 boats each winter. The majority of them become sedentary for the season but that's not what I'm about. I'll only stop short of adding metal plating to my bow.