Try Cape Air out of HYA. They have a boat load of 402s in St Croix. St Croix is a fantastic place to live too. Inexpensive and beautiful.
There are alot of freight dogs in San Juan as well. Try Merlin Airways ( FedEx feeder ) Billings MT. They fly Metroliners - sorry I dont have a web address or even a phone #. Also Sundance Air in Denver ( UPS feeder ). They fly 99s and 1900s. They both base A/C in San Juan. Good schedule, decent pay. Last I heard sundance wasn't hiring, that could easily change tho. I have heard nothing but great things about Cape Air - too bad they only have 402s tho. But if you like the lifestyle than who really cares what the equipment is. You might also try sending a resume to Bill Bohlke. He owns FBOs in St Thomas And St Croix. (340) 778-9177. Good luck and blue skies.
BTW Island flying is different then any other flying.
I flew down there the winter of '98-99 for a little local outfit with a few Islanders. I had @2500 hrs with a few hundred multi and an atp when I went. Anyway, I started by faxing resumes and heard nothing. So I just went down to SJU in October (the beginning of their high season) with a stack of resumes. I was returning to a job the next summer and told the companies that, which lost me a few opportunities, but oh well... Still, I got a few offers within a week--of course the hiring environment everywhere was different in 98, but your time should still be competitive. My advice is to go down to SJU and hang out and bug a few places--this may not be the case with Cape Air or Air Sunshine but with the local places that's how it works. Everything, including hiring and training, operates on island time--read as VERY SLOWLY. Having an ATP is important since its almost all 135 twin scheduled ops. I know such a plan isn't feasible for everyone, but it worked for me.
I haven't been back in three years so I don't know who is still in business and who isn't, but just surf the net for Caribbean operators--if their website is still up, chances are they're still flying. Some to start with are Vieques Airlink, Fly BVI, Air Culebra (a one-man ops the last I heard), Four Star. I heard its best to avoid Air St. Thomas and Tolair, but that's just rumor.
A last bit of advice--try to live on one of the smaller islands. I heard that St. Thomas and SJU are no fun to live in (I'm sure some American Eagle folks could vouch). We lived on Vieques and loved every minute of it. I had a blast and met some really interesting folks. And watching the sunrise every morning over the VI from 1000' above the water was awesome. It would be a fun place to ride out a down-time in the industry. If you can, go. Take it easy and be safe.
This subject gets a fair amount of play on
this board every winter, perhaps you can
find some past info by searching for the
subject, if you haven't already.
I looked into it pretty extensively a few
years ago, went over there a few times,
and got a couple of offers. I didn't end up
taking it; worked out of Lauderdale
instead. Here's a very condensed version
of what I found, search and maybe you
can find more. This info is four years old, but things change slowly in the islands.
1) Season is from November 'til April, with
some layoffs at the end of season.
2) Many of the carriers are scheduled
operators, even if it is just a beat-up
Aztec. That means you must have an ATP
to fly PIC for this type of operation, and
island operators do not give up a potential
pax seat to have SIC's . . .
3) If you have less than 1200tt (non-sched
PIC IFR mins) you will need to find
companies flying aircraft that require a
SIC, like a DC3, DHC-6, Trislander (don't
ask) or similar. These jobs will usually go
to locals, but you never know.
4) Most activity in the Caribbean is
centered out of San Juan, PR. The best
way (almost the only way) is to go there,
and start knocking on doors. Go to the
charter terminal, and go dowsntairs. talk to
the pilots, see who is hiring. Don't forget to
go to Isla Grande airport, over by Old San
Juan. Don't be surprised if you run into
other pilots doing the same thing. Lots of
guys come over looking for work, few stay.
Expect to have to overcome this
5) Your best bet, if you want to live in the
islands and work as a pilot will be to work
for Eagle. You will have dependable pay,
jumpseat benefits, and the ability to
transfer out once you get over the whole
beach bum deal, which will eventually
happen[obviously, this has chenged, but there are still some commuters hiring down there, like Cape Air).
6) If I still haven't talked you out of it, go to
the RAA website (http://raa.org) and look in the member
directory. You'll find a directory of 135 and
121 cargo companies, some of which will
be in PR, with contact and fleet info.
I go to Belize all the time and a few operator down in that neck of the woods hire Americans. I know of one good one called Tropic Air. They fly 172,207, and a bunch of Caravans. No twin time but a lot of fun. Only three paved strips in the whole country and a lot of flying. The pay for the Caravans is like $25US and hour and that goes a ways in Belize. Don't need a car, and rent is relatively cheap. They usually start people with 500 hours in the 172, progress to the 207 at 1000 hours and 1500 hours and a one year contract puts you in the Caravan. The contract is because they send you to flight safety. No ATP required. It is Belizian CAA not 135 so you need a conversion which includes and short written test and the inspector looking at your log book. The chief pilot, CEO, and president are all Americans. Good operation, with good mx. Not restricted to island hopping. They do a lot of flying to Guatemala (Tikal).
Another company called Maya Island Air also flies the same places. They have a few islanders, a handful of Caravans, 172, 207, 182. They also hire Americans. I don't know a lot about them, but they are locally owned.
Good luck with the job hunt.