Where do I start?
 

Currently I'm still doing my training in Canada and when I finish I'll have my CPL. I grew up in Bermuda so I have a strong desire to fly in the Caribbean, and I'm trying to figure out how do I go about doing that? I've been reading other posts and comments but all the questions and answers seem pretty specific to the person wanting the help you know? Also the posts I've been finding seem pretty old.
What I want to know is, how do I open communication with different companies that fly down south? Do I just run a google search and send an email to whatever email address I find under 'contact us'?
I've been looking on 'pilotcareercentre.com' so far; is there any other website specific to aviation companies in the Caribbean?

You do the research yourself rather than waiting for somebody else to do it for you.

Once you have your CPL/IR , you need to get down there and knock on doors, it's as asimple as that. Take with you 3 white shirts/uniform pants and be ready to work. Take any job as a foot in to a aviation company.

I agree with our Bermudian fellow rather than with Shytehawk. In regards to the Caribbean I had been struggling to get information for almost 5 months now. I did my research in Linkedin, Facebook, Google and I only found one guy in all this time that took the time to write me an email with a few facts.
I flew before in Namibia, place that I found through PPRUNE and there is a lot of information about it.
But when it comes to the Caribbean that information its missing. I got not even a "No" from more than 50 companies I contacted during this period.
I do agree however, that we must go there and knock the doors, but for example, if you try Bahamas... been there without a job can cost you the same than C208 type rating per month...and of course thats not including ticket.
So if someone in this forum is kind enough to help us, we will be very pleased.

I hate to say it but try Seaborne, Cape Air, M&N aviation, IFL and a host of others.

Yes, if you REALLY REALLY want to fly there you'll have to go there. Seaborne would take you tmo but be forwarned.

Seaborne, Cape Air, M&N and IFL requirements:

FAA license
Green Card

None of them will hire a Non American citizen...

Struggles
 

If you dont have a pilot license from your nation, then its somewhat difficult. With Bermudan citizenship and a Canadian license you would have to work for a Canadian registered outfit in the Caribbean, which are next to non exsistent.
Most operations are of their respected nations or US based. The US based companies require FAA certified pilots and Part 135 or part 121 flight hour requirements and in most cases a US work authorisation (1500 hours total + other hours requirements).
The other operations of their respected nations also parrallel the FAA system which must also meet ICAO standards. In other words, your need 1500 flight hours and some places specific type ratings.
Your best chance at working in the Caribbean is to get an instructors' licnese and build flight time in Canada. If your flight school cannot authorise the permit to work in Canada, Then get the Instructor ticket and head to somewhere in the world such as Africa, middle east, china, korea, malaysia, indonesia, india, guyana.
Get those hours and go where your dream tells you.
No airline will even tell you "NO" without close to the required flight time.

Source: myself
I was in the same position a decade ago. Now I am pilot in the Caribbean.

Yeah it's not so much that I'm not doing my research its more that I can't just show up in the Bahamas and ask for a job because its too expensive. Also I kept getting the feeling like most of them say they are an airline based in the Bahamas or St Lucia but they must have a main hub in Florida. So wouldn't you go to Florida? That would be a lot easier and cheaper than island hopping. I mean surely if you have a hub in the Bahamas and you have 12 planes in your fleet, you would have to search outside of the island for pilots anyways. Your not going to hire just the people who come to you because there wouldn't be enough pilots knocking on your door.

I actually have 3 citizenships, USA, UK, and CAN

1. If you're originally from Bermuda then you should know that Bermuda is in the Atlantic not the Caribbean. BTW, the Bahamas are also in the Atlantic and the Caribbean does not touch them anywhere.

2. There are no Canadian territories in the Caribbean. Therefore your Canadian citizenship is of no particular value for what you want to do.

3. Your USA citizenship will be of value in the US Virgin Islands and Puerto Rico. You will also need an FAA license or US validation (of your Canadian pilot certificates} to work in either one.

4. There are only 4 British Overseas Territories left in the Caribbean where your UK citizenship might be of value. They are Anguilla, The British Virgin Islands, The Cayman Islands and Montserrat. You may live there but you will still need a work permit to work in any of them. Again, you would need a validation of your CAN licenses as well.

5. All of the remaining Caribbean islands are either independent nations or French or Dutch territories. Each of them would require a work permit and a validation of your Canadian certificates to work there. In the French islands that's impossible. On the others it is possible but difficult. They ALL give preference to their own nationals.

6. In my opinion your best bets would be the USVI, PR, the BVI or St. Martin, in the Dutch West Indies. It would make no sense at all to try going to all the islands.

7. Find out what companies operate on those islands in #6 and make contact with them directly. If they want to see you then go, if you think they're offering what you want or need. Otherwise you'll be wasting your time.

Otherwise if you think you like the island where there's an opportunity and you can afford a vacation there, go for it. Remember, the cost of living is NOT cheap on any of the islands.

Hope that helps some. I'm not trying to discourage you, just being realistic.

Whatever you do NEVER give up on yourself. It's not easy but if you keep trying one day you'll get the answer you want. It's kind of like flying .... you can't make a good landing if you stop before you get it on the ground. Persistence is key. Strive always to be the best at what you do. Learn always ... that's what makes the difference between a pilot and just a dude with a license.

BTW, if you don't already have it, get an IR, an ME and an Instructor's rating if you can.

Good luck.