Relative Newbie Looking for Shallow, Low Key, but awesome Caribbean divesites!

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I agree with the others that Bonaire is probably a really good choice, just read very carefully about how to avoid the theft of your gear.

As for Little Cayman, the walls are definitely a big draw, but I rarely spend much time over the edge, except on sites like Randy's Gazebo where the wall geography is part of the beauty of the site. The real action on Little Cayman is mostly on the top of the wall in the shallows (<40-50'). Your only problem as a solo might be finding a buddy who doesn't at least want to take a peak over the wall at the start of the dive. You might also reconsider your 40 ft limit, as the conditions on LC are generally very mild, with little or no current to speak of and rarely any issues with downwelling or upwelling along the wall. My wife and I went to Cayman Brac as our first dives post OW and AOW, and had no problems at all diving, as the conditions were so mild and easy to dive in.
 
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