We went to Negril in 2006 and Ocho Rioc in 2011. In Negril we stayed on Bloody Bay, where most of the AI's are located. We stayed at the RIU Tropical Bay, which I cannot recommend. The food and atmopshere were just terrible. Across the street is Sunset at the Palms, which I wish we would have stayed at instead.

We have stayed at 2 Sandals resorts in other destinations and I could not see paying that much money again as we didn't feel we got our monies worth. However, the Sandals Whitehouse gets pretty good reviews in that area, but it is very secluded about an hour outside of Negril.

The Couple resorts, just like Sandals, have their loyal followers and dedicated haters. I avoided them due to price and their nude policies. Not our type of atmospher either.

From Negril, you can go to the YS Falls and the Mayfield Falls, which I thought were so much nicer than Dunn's River Falls. There is a tour that will take you to the YS Falls, Black River and the Appleton Rum Factory. It's an all day tour.

In Ocho Rios, we stayed at the Jewell Dunns River resort, which was formally the Sandals Dunns River Resort. We enjoyed our stay there. The food was good, atmosphere was nice and though I don't really care for Sandals in general, I do so love their huge pools.

We went to Coyaba and Shaw Park Gardens. The waterfalls there was also much better than Dunn's River Falls. We also did the raft down the Martha Brae. We found the locals in Ocho Rios way more aggressive than Negril. We went to the Island Village shopping center and it was just a horrible experience. It is best in both ares to hire a private driver or go with the resorts tours just so they can keep the aggressors at bay.

I feel the Montego Bay area has the best AI hotels, but it's just not the best location. The Iberostars and Secrects resorts get excellant reviews in Mexico and also have resorts in the DR.

JTL Tours is the local tour operator for Jamaica. Here is their link. It will give you an good idea of what you can do in each area:

http://www.jamaicatoursltd.com/

We used A to Z Jamaica Planners in Ocho Rios and I would highly recommend them.

http://www.a-zjamaicaplanners.info/

I felt the Ocho Rios area had the better selection of AI hotels over Negril and more things to see and do off property.

If you are interested I have our vacation photos of each area:

Negril:

http://kvrlvnphotogallery.shutterfly.com/pictures/4049

Ocho Rios:

http://kvrlvnphotogallery.shutterfly.com/pictures/443

I think both areas have their good and bad points and that you probably just need to try both areas like we did. If we ever do go back, will probably stay in MoBay just because we haven't yet.

I only know (and love) Negril. But it's a pretty laid back spot. A little more rustic generally speaking than it sounds like what you are looking for.

I am a big fan of Negril, but I agree with Suze that it doesn't sound like a good fit for you. Regardless of where you decide to go, please check stats for weather in late May. That can be a very rainy time in the islands. We used to visit at that time and don't anymore.

Montego Bay gets a bad rap but I think it is a good spot to be if you want to be centrally located to excursions and entertainment. It is a city and the beach is not as nice as Negril, but you can easily take a day trip and spend the day in Negril anyway. If you want to go AI, there are way more All Inclusive properties in Montego Bay as well.

Some of the beaches at the resorts in Mobay are rocky once you go a bit out and I can't comment on the beach at Sandals Mobay but it does not look very rocky by the pictures.

Take a look at their TA site and look at the pics for yourself:

http://www.tripadvisor.com/Hotel_Review-g147311-d151461-Reviews-Sandals_Montego_Bay-Montego_Bay_Jamaica.html