Start by going here:
http://www.google.com/advanced_group_search?hl=en

In the box that says "with all of the words" type Caribbean
In the box that says "newsgroup" type rec.scuba.locations.
Where it says "message dates" you might want to choose something less than everything
since 1981.
Go to the bathroom and have something to eat first. You're going to be there for a
while.

That's one option. Better still, find a dive buddy and put some confidence in what
you've learned about diving before getting there, and just go diving. It's goint to
cost extra if you want somebody from a dive op to actually watch over you. FWIW,
depending on your schedule I'm probably available. I'll need to take time off from
work, but I can still do it for expenses plus $200/week, as long as you only go for a
week or two.

Like almost all of the questions you've asked here, your instructor and/or dive shop
can help you out. Not only are there companies that specialize in dive travel (to
almost any place that offers diving), they will pay a commission to the dive shop.
That will make the shop happy, and you may even be able to get them to share the
commission in the form of a better price on some gear.

By focusing on the diving, and less on the details.

Where are you now?

Can you dive there? (the answer is probably yes, although the diving
may be far less than ideal). Many of us live in decent diving locations
and dive locally a lot, but still travel to distant dive locations (for
example, I live in San Diego, but dive in SE Asia somewhat regularily).

If you want to travel to dive, where can you travel to? Where is too
far or too expensive? Are you travelling with non-divers?

rec.scuba.locations is also a good place to post your travel related
questions. I've cross-posted this to r.s.l, so you might want to check
out the responses there as well.

Alan

You post things like this and wait for everybody to respond with their
favorite sites, tell one another why they're wrong and then fight over who
said what to whom.  Eventually, the discussion will revert to guns, sex,
politics or a combination of one or more of the topics.  At that point, or a
bit earlier if you're lucky, you quit reading the thread.  You also review
all the magazines you can find, all of which will tell you that every
resort, on every island in the world, is the most wonderful place you'll
ever hope to stay and dive.  I almost bet there's an article somewhere that
concludes some shop in Kansas has the best places of all to dive.
Advertisers tend to get favorable reviews.

When you've got all the information possible, on all the sites around the
globe, you'll do what all the rest of us do, pick one and take your chances.
Experience is the best teacher.  Of course, the experience of those you can
trust, including some that post here, can help.

Why would you pay to travel to the Caribbean and not look for the best dive
sites?  Don't be silly.

There's no "of course" to paying a company to supply you with a guide and, I
hope, you don't need somebody to watch over you.  You are certified, right?
Your card does say that you're qualified to dive unsupervised, right?  The
only "of course" is that you want to book your diving with somebody that
will accomodate your preferences for dives that are within the skill range
your card suggests.

It's been a while since I've been there, but Sunset House, on Grand Cayman,
is the kind of place I would recommend.  When I was there, the dive
operation was top quality and, more important to your needs, they ran more
than one boat, with each boat catering to people of different skill levels.
The dive sites, including those where relatively less experienced divers are
taken, are all very nice, full of colorful coral and lots of fish.

How about a combination of the two.  Diving in Florida is likely to be more
economical than travel to the Caribbean and, in my opinion, is every bit as
good an introduction to ocean diving.  The most popular diving is probably
in the Key Largo or Islamorada areas.  Dives tend to be shallow, with low
current.  Some have very nice reefs and most have a lot of fish.  They Keys
are not real cheap.  The Miami area has some nice reef diving, particularly
out of Biscayne National Park.  They also have quite a few wrecks, some of
which are shallow enough to interest a relative novice.  BTW, stay on the
outside of wrecks for now.  The Ft. Lauderdale area is also very nice.  The
reefs are only OK, but the wrecks are very nice.  At the bottom, they're
also on the deepish side for a novice, but the tops are within the range
your certification suggests you should be OK at.  Personally, I like the
land activities of the Ft. Lauderdale area better than either Miami or the
Keys . . . which is part of why I live here.  Boynton Beach, which you'll
find discussed often in this forum, if the favorite of many of the people
here.  Mostly, this is drift diving at moderate depths, anywhere from 40 to
80 feet, give or take.  The reefs are nicer than those in Miami or Ft.
Lauderdale and the fish life is more diverse.  Personally, I like some of
the best reefs in the upper and middle Keys better than Boynton, but mostly
because I find good visibility more predictable in the Keys.  The fact that
I dive the Keys from my own boats has something to do with my preference.  I
dive Boynton more often simply because the logistics are simpler for me.  We
like Splashdown Diver and Deeper, both operating out of the Sea Mist marina
in Boynton Beach.

The one thing that many of us find most important, is who we share our dive
with.  I tend to travel with the people I plan on being a buddy with.  Lucky
for me, my wife is a diver.  Those that don't have a regular buddy or don't
have one that can travel with them, have to take the lucky of the draw and,
sometimes, the draw isn't all that lucky.

Lee

The Keys are a good place to start.  Easy diving shallow reefs (all boat
diving).  Key Largo, Marathon, Islamorada, are all good.

Grand Cayman is very expensive and you would want to dive the 7 mile
beach side (the most popular)  the east side is rougher water since it
is the windward side.  I think almost all sites are buoyed - although
some won't be.

Cozumel is very good - all drift diving. Did my first diving there - may
not be the smartest thing but they diving was easy and spectacular.  The
currents can be ripping at some places and non-existent at others.

Bottom line - figure out what you can afford and do it.  Most divers do
their own planning, but many places offer dive packages.

Step one... get a map of the Carribean.
Step two... acquire a dart.
Step three... Hang the map on the wall (preferably one that you don't mind
having holes in... or you could mount the map on a dartboard bfore hanging
it on the wall)
Step four... throw dart at map in such a way that the pointy end will stick
into the map
Step five... determine the island closest to where the dart landed
Step six... come back here and ask us if the island has good diving
Step Seven... if the island has good diving, call your travel agent.
Otherwise, return to step four.

Blackbeards.

 Florida is the best bang for your buck, but everyone's milage may vary.
   
         
                                       Popeye
                "I didn't attend the funeral, but I sent a nice
                 letter saying I approved of it." - Mark Twain

The process of setting up a dive vacation isn't all that different from
setting up a normal vacation:

- pick where to go, and how to get there
- decide where to stay
 - decide what you're going to do when there

Well, you don't want to go to a place that stinks either  ;-)

One good way to start is at a travel agent, for the primary purpose of
picking up a couple of those free magazine-like pamphlets that a couple
of travel consolidators publish.  They typically have listings of
several islands with general descriptions and a bunch of hotels for each
island with various prices.

While you're out, pick up some scuba diving magazines.  For this
exercise, pretty much "one of each" off the rack will do.

First, sit down and read through the travel agent stuff, focusing mostly
on the general island descriptions - what kind of stuff is there, etc.

A couple of islands will probably turn you off and a couple will attract
your eye ... you want to figure out why (what's the common theme or
pattern?).  For example, if you don't care for gambling, you might do a
thumbs down on islands that list casino's as a noteworthy attraction.  
Similarly, if you're not a particularly well experienced traveller, you
might want to lean towards destinations where English (or whatever) is
the official (or is at least a very commonly spoken) language.

After you've started to get a general feel for things, now you can start
to look at the dive rags.  Naturally, every article will have wonderful
diving.  The things to note are which diving descriptions catch your eye
more than others, and which islands that you thought that you might like
(or dislike) from Step #1 are repeated here...this helps you refine your
list again:  if its somewhere that you thought you might like plus
someone's bothering to write about the diving there, you probably have a
destination for your short list.  Now you can look at budget :-)

The "real short list" for Caribbean diving in general is going to be the
Florida Keys, Cozumel, Cayman and Bonaire.  Each has its strengths and
weaknesses, including cost.

A lot of us probably have a short list of "old standards", and we'll
then consider new-for-us destinations based on something we've heard.

To boil down all the logistics to its simplest form, it is then:

1.  Flight
2.  Accommodations
3.  Dive Operation
4.  Local Transportation (eg, rental car)
5.  Booking/Reservations
6.  Passport
7.  Gear
8.  Film
9.  Cash
10.  Go

-hh