Just spent a little more than a week and a half in Jamaica and had a fantastic time although this was definitely influenced by the fact that I got married and had my honeymoon there.
I'll add a few words at the end about my destination wedding for those who are looking for advice, but start with the food report.
We spent the first 5 or 6 days at the Tryall Club located about 12 miles west of the Montego Bay Airport (towards Negril). Although the restaurants at Tryall are nothing special and a bit overpriced, what is wonderful about Tryall is that if you can get a 2 bedroom villa or larger, you get a chef with the villa who can make whatever you request. You only pay for the ingredients and you tip the villa staff - which also include for most villas a maid, laundress and gardener (and for a deluxe villa can include a butler) - on a daily basis (tip is about $25/day/room split between the staff and ingredients run about $35/person/day). You can ask for authentic and spicy dishes or simple grilled fish or whatever you like. We saved lots of $ on dining out and we found our chef very very good and willing to work with us on getting great local produce and making some delicious authentic dishes. If you aren't happy with the quality of the grocery available on premises, you can authorize your chef to go elsewhere for groceries. Although none of us have a staff back in the states, we all managed to put aside our liberal guilt and adjusted a bit too quickly perhaps to having our laundry done, rooms cleaned and meals prepared for us. (you can put your comments about whether this was a good thing or not on not about food or another website.)
Outside of Tryall, we stopped at 2 jerk spots - casual side of the road open air places - Mackee's and Scotchies - both were on the main highway (A1) between Montego Bay Airport and Ocho Rios. Scotchies was wonderful! It's about a 5-10 minute ride from the Montego Bay Airport. The chicken and pork were moist and juicy and well spiced and you could add a hot sauce if you wanted it lip & tongue tingling. The fish was good, but not as good as the chicken and pork. The sides were fine, but not tremendous, incl. the breadfruit, festival & sweet potato - a bit dry and tasteless. Prices were on the inexpensive side and there's a nice seating area in the back with flowers and a couple of tables. Scotchies is mostly frequented by locals, including our chef at Tryall who eats there at least once a week. Mackees was similar to Scotchies in set up and dishes offered but at least 30 minutes further towards Ocho Rios. The chicken was pretty good, but the pork very dry and not nearly as good as Scotchies (we hit Scotchies twice on our trip - incl. a last minute stop on our way to the airport). Prices were about the same.
The rest of our meals and the remainder of our trip (our honeymoon) was spent at Goldeneye in Oracabessa, Jamaica. Goldeneye is an all inclusive for the wealthy - it was definitely not cheap - about $300-$350/person/day for lodging and food and alcohol and taxes and a 5% tip to the staff. Wine and beer and liquor was all included and your villa is stocked with whatever you like. For an all inclusive, the food was actually pretty good (we'd give it about a 21 to 23 Zagat rating). Lunches were buffet style and some of the dishes would have been better if they hadn't sat out - but the plantains were wonderful, the ackee & saltfish delicious and the barbecued food finger licking good. Dinners were served either at your villa or at the gazebo restaurant and were fancier - with white tableclothes and dishes such as grilled lobster, steak, rack of lamb & braised oxtail. The oxtail was falling off the bone and in a rich brown sauce that was fantastic. They accented their dishes with local seasonings - but kept it light for the tourists - so if you're looking for authentic, go elsewhere. For breakfast there was great fresh fruit and cereal and eggs any which way most days (we did have a nice vanilla french toast one day). The omelettes were just the way I like them - browned and crispy on the outside and mixed with vegetables and a great cheese that infused every bite.
DESTINATION WEDDING ADVICE:
For those looking to have a destination wedding in the Caribbean - I HIGHLY recommend where we had ours - The Tryall Club. It exceeded all of our expectations. The setting is gorgeous - we got married with about 90 guests next to the ocean with the sun sparkling off the water - and had a fantastic reception at the great house on the hill under a full moon with a fantastic view of the resort, the ocean and Jamaica. For our dinner we had suckling pig - moist, tender and delicious with a crispy skin, grilled lobster, curried goat and grilled Tilapia - all quite good as well. Herbert Baur who is in charge of handling weddings at Tryall took excellent care of us! He never books more than one wedding per day (which most resorts do), he acted as a wedding coordinator for free - helping find a florist, band, dj, photographer, etc. and making sure they were all there and doing what they had to do, he arranged a party the night before to welcome everyone with a steel band and food & cocktails and a goodbye brunch the next day. (If you need more info., you may e-mail me at firstname.lastname@example.org.) And ALL of our guests were thrilled with the villas at Tryall and the whole experience. A number of them said it was the best wedding ever and the most fun they ever had at a wedding.