Hi, I live in Texas too and I have been on multiple cruises, including the 3 places you are going. We did this travelling.
I can't say a lot about of what I did because I am under 21, because most things are usually adult orientated (21+), so cruises have been a bit eh for me until I turn 21. I can't remember the first two ships I went on, by my latest was on the Freedom. Huge ship, definitely better food than the last two for sure, I love cruise food, it is actually really good.
But for destinations....
Key West was extremely boring, then it started to pour, trapped inside some mall that looked like it was built in 2 days with no AC and hundreds of people. I fail to see why people really like it so much.
Progresso was awful, beach looked like Galveston, just with added umbrellas and chairs, and people trying to survive by pestering you about a hand crafted necklace with plastic shells. We walked through the street down to the beach and it was awful too. Just another run-down, poor, port city. Think of it was junky Key West.
We went to Nassau (Capital of The Bahamas). So I was really excited for that, clear water, nice beaches, great weather. Complete opposite, back to Galveston beaches. The shore is covered in tiny broken shells, every step you take hurts your feet, there was a little trampoline that was a bit out so you could jump on it but how do you get off? Jump down into some sharp shells and rough coral. The only good thing there was the buffet, that lasted for 5 minutes.
Freeport was just stupid.