I've done both: a Hilton all-inclusive outside of Montego Bay, Jamaica and a 4-day cruise on one of the smaller Royal Carribean boats from Florida, down to Nassau and then to their private island for the day. I enjoyed both very much, but I probably leaned to doing another cruise as I love being on the water.
Jamaica was fun and the hotel was awesome. We did go on an excursion to swim with dolphins was fun and we drove around Jamaica, which was eye-opening and beautiful at the same time. Since it was hotel-run, I didn't feel super uncomfortable. If it was just my wife and I, hell no. But by the end of our stay, I was ready to go. There's only so much you can do and the food wasn't as diverse as the cruise.
Our cruise was fun. We were with a group of about 12 people that we didn't know and it was nice to be kind of forced to meet people. There was always stuff to do on the boat and as long as you're not on a Disney cruise, kids were almost non-existent (every ship has adults-only sections thankfully). Food was pretty good, and the drink package is super expensive, but worth it. Food was awesome. You can also bring a bottle of wine per person. It was fun to get off the boat each day and see different places as long as you stay the hell away from the tourist traps. We did have a super-obnoxious Zumba group on our boat, but thankfully we only saw them at night. The coolest part for me was we got to watch a pod of dolphins ride the boat's wake into Nassau for like 45 minutes. That was awesome. My only complaint is the bathroom in anything but the suites are like a phone booth.
I was reading about the cruise around Cuba and that looks really cool. I would just suggest finding a smaller boat as the ones with 7000 people would kill me.