Cuba, Antigua, then Dom Rep first time.
Cuba we were really ill and we're upgraded because the all inclusive hotel food cleanliness was very questionable, but being upgraded when you are fighting each other for the bog is not really a luxury. You know when you are shitting water so much that you have cramps, and then there's nothing left in your arse but the cramps are still there? Yeah, that was that's Cuba for us. Situated in some swampy mangroves that stunk and mosquitoes everywhere. Had to have a cigar at all times to clear them off. But the cigar lounge and drinks were top class, guy there called Ruben who had worked at some big hotels in America and knew his stuff. Went on a day trip and got left in some village where our chewing gum was taken from us, I think in return for just letting us be there. Saved us that, a proper whiskey sour and a cigar.
First Choice didn't give a crap when we got back and felt like we'd spent hundred of pounds on giving ourself the squits in a hot, sticky country. Holiday was also sold to us as a Robinson Crusoe type escape, they failed to mention it was also Canadian spring break, and the Canadians at the time just loved going to Cuba especially because their American cousins couldn't. Kids drinking and spewing all night, fights, used condoms on the beach. Gave Blackpool a run for it's money.
Antigua was great except for two things. My missus got far too squiffy on white rum on the first night and was ill for days, and near the end of our trip we were held up by a guy with a machete who decided to stop our taxi randomly. Taxi driver was off his tits on something, but thankfully they did a deal and we got back to the hotel.
Dom Rep in third place because it was my first big holiday outside of backpacking. It was basically magaluf in the Caribbean, pissed up Brits en masse, drinks in plastic cups like at a kids party because nobody was trusted with glass, strongly not recommended to leave the secure hotel complex, but when we did it was actually the best part of the trip. Plus it was ridiculously hot and you couldn't move without dripping, regularly over 100.
Don't get me wrong, all fantastic places and glad I went, well maybe except Cuba, but that was probably our hotel choice rather than the country.