BoKnows

If you're mostly going to stay at the resort, just go with whatever's cheaper.

Grand Bahia Principe resorts (grouped together) in Tulum were quite the gongshow when I was there.

I would recommend any all inclusive resorts near Playa del Carmen, just south of Cancun.  Wouldn’t go less than 4 star.

Drink all day at the resort, go to Coco Bongos in Playa for party time. There’s many other bars in Playa, the Senior Frogs had margaritas in glasses so large, it fit on my head like a football helmet. 18 oz tequila in it.
Depending on which resort you pick, you can stagger back or cheap cab.
Bahia as someone mentioned is a good resort, one of the furthest south resorts. Huge resort, they have large golf carts to shuttle you around, and tequila tables everywhere. 

google map Playa del carmen, zoom in, you see which resorts are right in Playa, or near Playa. (Fun to do thing if you stay in/near Playa, catch the ferry to Cozumel, go snorkeling for the day, ferry back, continue drinking)

Jamaica is beautiful, north coast is cheaper than Negril, but still not cheap. Perfect if you just stay on resort and pound drinks at the swim up bar. Depending on your comfort level, wouldn’t wander off resort at night.

Go Canucks!