Have you checked out tripadvisor.com? You can look up most resorts there.
If you like to go out at night, I would recommend the Riviera Maya. Our resort (the princess) had several families who were return visitors, so I think that is a good sign. In addition to two main pools where they had games/sports, the pool was this huge moat that went around the whole resort. People on the bottom floor with swim-up rooms could walk into the pool from their balconies. It also had several restaurants in addition to the buffets, which brought more variety into our eating options. It had a shuttle into town so we could hit the clubs there as well. Even though we could drink for free at the resort, the drinks at clubs were quite cheap and it was nice to have the change of scenery being at the same resort all week. The discos at resorts are usually kind of tame (or full of kids, heh). Of course you can have fun anywhere under the right conditions and the all-inclusive drinking helps with that 🙂
Montego Bay also had a few clubs the resort provided a shuttle for. I’ve heard it can be sketchy at night in town, but that wasn’t my experience at all. There are also excursions available to Dunns River Falls (a waterfall you can climb). The Reggae band the Holiday Inn brought in on the weekends was AMAZING.
We went to Cuba but I’m not sure if Americans can go there without flying to Mexico or another third country first.
Another Mexico destination we loved was Huatulco, way south on the Pacfic coast (far from PV, Manzanillo, Mazatlan, etc). It is a cruise ship stop with gorgeous beaches and really cute little towns. My grandparents renewed their vows on their 50th wedding anniversary in a beautiful church in town. We stayed at the Barcelo. Best food ever, seriously. They made a huge Paella on the beach every afternoon, and if you timed your eating right you could live off of freshly-BBQ’d meat and fish and avoid the buffet completely.
The Occidental Grand Papagayo in Costa Rica was breathtakingly beautiful. If you walked down the beach for 15 minutes, you could see cute spider monkeys. There were also big monkeys in the trees in town. We did a zipline tour, a mud bath/hotsprings trip, and horseback riding. My grandparents did a river tour of the jungle and saw all kinds of cool birds. I would suggest bringing lots of bug repellent for those trips. We spent the nights partying at our resort, which was full of people our age that week. Fun times!
I was younger on our trips to the Dominican Republic, so I didn’t go out at night. The beaches at both Puerto Plata and Punta Cana were AMAZING. Seriously, you could walk for hours on the coastline. The Coral Marien is where we stayed in Puerto Plata, and the Breezes is where we stayed in Punta Cana. Breezes was too crowded and noisy for my mom’s liking. They did have a lot to do, though. They even had this skating rink made out of plastic that you could "ice" skate on with hockey skates on the beach. Made for fun pictures… I think they also threw in a free banana boat ride or maybe it was a free power boat activity, so maybe this might help with your parasailing plans?
To be honest, all the resorts are kind of the same to me. We pick our holidays based on who is offering the best value in the 4-star range. The staff is always great, the drinks are consistent, the grounds are beautifully maintained with cool tropical plants, the entertainment is always a bit hit or miss (except for the musicians, who are usually great), the food is ok (but you always get a little tired of it by the end of your week or two) and they’re usually close to other resorts and a town where you can do the kind of shopping you want to do. I never had problems with bugs at any of them, except for all the bites I got in the jungle on excursions. I think all of them have parasailing, too. I remember seeing it everywhere!