Hi joljaz and welcome to thescubasite
The Caribbean is where I learned to scuba dive and it's still one of my favorite locations, definitely some of the best diving in the world round there, so snap up the chance!
In answer to your question about ear pressure, it is perfectly normal.
Your body has several "closed air spaces" - that means places your body holds air that aren't "open" to the surrounding world. When you dive deeper, the pressure of the surrounding water increases and this the pressure on the air trapped inside your ear also increases, which makes it shrink and causes "squeezing" feeling.
What you are feeling is the air within your ears being pressurised and the water "pushing" on your ear drum. It's not something you can become immune to - you have to equalise the air pressure. I suggest you read our article on
ear pressure equalisation which will show you the few, simple techniques to alleviate this discomfort.