What's up my bros - was wondering if people with similar experiences or insight could chime in on some of the mad schemes I'm going to try to pull off

I grew up in and live in the Canadian Maritimes. 30 years old. I have a good buddy who makes great money as a pilot who is in the process of buying a good comfortable long range blue water cruiser and the dream is to live aboard and sail south for the fall, winter, and early spring. We have both had enough of Canadian winters and his work will fly him back and forth. I have a pretty crazy good bartending, hospitality, service management resume with a couple of years experience sailing tall ships. What is the feasibility of finding work in the Caribbean or even the Florida Keys? I've been doing a lot of research on how difficult it can be to find legit work in the islands but a lot of Caribbean bros I'm friends with up here seem to think it won't be that hard for a fit young white dude to find something. Any recommendations for places to go - businesses to contact - things to start working on, etc. I've started reaching out to major players like club med and other resorts as that seems like the easiest way to get legit work

>>2788477 (OP)
Hey, there's a sailing general on /out/, you might have more results if you ask there. THey are generally pretty knowledgable. I'm also a 30s east coast canadian looking into the same thing. I have a 27 footer in the great lakes but going to start taking many weeks off work, 2 months a year, and might do the same thing.

>>2788785
Appreciate it brother, I'll try there

Bumpuddu bump

>>2788477 (OP)

High risk of piracy. It's gotten worse in the last 5 years and it was getting pretty bad going into covid. I gave up the idea. Northern Caribe is an arguable no go zone.

>>2789409
Coward

UHMMMMM.... BUMP??

Well enjoy the expensive upkeep when you’re really using the boat and depending on it with your life to sail any distance
The stats aren’t too bad if you don’t do anything completely crazy but theres always suprise weather that the forecasts missed and years of pleasent sailing can then go completely wrong
You’re not used to high winds a storm and huge waves and then you realize you’re last chance is some shitty life raft which you hope everything functions on perfectly and which can transmit your location to the coast guard and they can find you or even attempt it
It happens and most people think they are good sailors and just really are not
All that shit on a boat just breaks sitting around eventually anyway so you can’t really cut corners
There’s just so many ways to fuck up and die but whatever everyone thinks their badass and it won’t happen to them

Most boat owners are retards and can’t sail in the first place so I have to place you into the tard category until proven otherwise

Even more so since you’re asking 4chan about it
You don’t know what you’re doing and I bet you’re buddy is some hack that doesn’t either

>>2791207
hell yea dude I've lived aboard before I'm more looking for insight into the best approach to work/life in the islands and discrepancies between them

>>2791426
I sailed around the caribbean for a bit around 2013/2014. I just lived a few months off of my savings but the work situation i could see was:
>no work at all at any of the lesser developed islands. And if there was any work, it would go to the locals.
>Some chances of some work at developed islands (anglo-speaking, european-influenced islands). Think Saint Martin and the like. Tons of work in Florida though, both in bars and boat crew.
From what I saw, no boats hire crew in the caribbean at all. They are there for leisure, not for business. If they need any crew, they call up an agency in Fort Lauderdale and the agency interviews and hires locally, having the employee fly out to the caribbean. I think the same dynamic happens in the hospitality business.

>>2788477 (OP)
how much for a boat?