We stayed in Montego Bay, which is on the north end of the island and the second-largest city after Kingston. Jamaica is a huge tourist economy, but the season is November - April, so prices were much cheaper for us in June, and we didn't run into hardly any parties of frat boys (and no hurricanes, either).
On our friend's recommendation, we stayed at the Royal Decameron Montego Bay, and after seeing several of the other resorts, were glad we did. For about $175 a night, we got a beach front room and all of the food and drinks we wanted (all the resorts we looked at were all-inclusive). The food was overall very good (local dishes and their take on other culture's cuisines - lots of fresh fish, lamb, chicken, steak), and the drinks were decent - and given what we drank while we were there, our liquor bill alone would have been at least that much anywhere else. My favorite drink was a dirty banana - blended rum, creme de cacao and fresh banana - but we had everything from straight rum to coffee with amaretto to old fashioneds (we had to explain how to make it, but they were game). You're also not expected to tip, and most people don't, but we found that leaving a dollar here and there got us significantly better service. While some of the other resorts were nicer, they were much further from town, and what we could have afforded would not have gotten us anything close to a beach view.
The trade off was that our room wasn't as nice - the bed was slightly hard, there was a water stain on the bathroom ceiling, and the water pressure in the shower was iffy - but we were fine with that given how great everything else was.
The food was served buffet-style, with many different options available. Colin hates buffets and he was fine with this because the food was so good. We ate with a beach view at every meal, a luxury that should not be underestimated. There is also a sit down restaurant you can make reservations for.
We found about a hundred different ways of doing pretty much nothing at all, which is exactly what we wanted. We'd wake up leisurely, meander down to breakfast, bring coffee back to our room, go down to the beach and read or swim for awhile, eat lunch, take a nap, spend more time on the beach, shower for dinner, eat more delicious food, get happily tipsy, fall asleep at the unheard of time of 10 pm, and do it again the next day. I finished three and a half books while were there and swam for at least an hour every day. Having nowhere to be and nothing we had to do was glorious. We would have had to pay for WiFi at the hotel, and there's no 3G access, so we had a nice break from electronic distractions as well.
We did about one thing differently every day, starting with a couple's massage in a cabana on the water, which was lovely.
We wandered into town a few times, which was easy to do on foot. The half-mile or so of the main road by the hotel is called the "hip strip," and its filled with tourist shops and bars, including a Margaritaville. The locals are very aggressive sales people - they call out to you from across the street to come into their stores and will keep pressing if you waver at all. Our friend had warned us beforehand, and a firm "no, thank you" worked just fine. We were disappointed in the cheesy made-in-China wares that most of the shops were selling, although we did find a good price on Appleton rum and Sangster's rum cream (like Bailey's, but even more delicious) in one of the little grocery stores. Also, if you're white, it's pretty obvious that you're a tourist, and you are therefore an easy target for less-than-legal substances. The second time we went into town Colin and I bet how many times we would be offered pot - he bet 5, I bet 10 - and it was 7 times total. Again, "no, thanks" worked just fine. Margaritaville was fun for the kitsch factor, but we didn't stay for more than a drink, as the appeal of free drinks back at the resort was too strong. They also offered yacht rides with loud 90s dance music, if that's your thing.
We asked one of the taxi drivers what we should see if we only saw one thing, and he recommended Dunn's River Falls, which is a long waterfall over 600 ft or so of rocks that you can climb. It was beautiful, but had been so mined for tourist purposes that we were somewhat disappointed. They had us climb the falls in long chains of 20 or so people, which was a pretty dumb idea, all things considered (and was frustrating for us, as we could have scaled it without help in about a third the time). They'd scraped the rocks of moss and carved footholds into some of them, and it was so swamped with people that it was hard to enjoy how pretty it was. I don't have any pictures of it - we didn't have a waterproof camera, and opted out of paying for their photos.
As the falls are near Ocho Rios, we did get to see a significant portion of the coastline and more rural areas as we went there and back, which was nice. We also stopped at a place near Discovery Bay that had absolutely fantastic jerk chicken (possibly the best of the trip, although to be honest they were all so good that it would be hard to rank), and would have been worth the drive alone. It looked like they were smoking it on wood poles underneath a sheet of aluminum. (I had my camera on the nighttime setting or something, so apologies for the poor quality.)
After using the snorkels provided by the hotel and being amazed at just the little reefs in the water by the hotel beaches, we decided to take a glass-bottomed boat out to one of the larger reefs off shore.
I had trouble with my mask and didn't enjoy it as much as I could have, but Colin loved it. The reefs weren't as colorful as the pictures of the ones you see in Australia, but we saw a lot of cool coral and a bunch of different fish, and the water was incredibly clear. We were also surprised that it went so far out and was only about 10-15 feet deep, and when there aren't reefs (or the wake of the boat), you can see straight to the white sand at the bottom.
The water itself was incredibly beautiful. We spent most of our time on the furthest south beach, as it was the quietest. I didn't get over that perfect turquoise blue the entire time we were there. The sunsets were incredible, and the resort faces west, so we had a perfect view. The weather report told us it would be thunderstorms that week, and although it did tend to get cloudy toward the evening, we got sprinkled on for about five minutes once, and most of the daytime was clear.
Cultural notes: our experiences with the local culture were admittedly quite few - restricted to those working in the tourist trade, and whoever happened to be walking down the hip strip when we were (still mostly part of the tourist trade). Almost 20% of the island is living below the poverty line, which was fairly apparent when we drove through the more rural areas. I wish I had read up more on the country before we went - I didn't know until after we came home than Rastafarian is a religion (and not actually a big one - the island is very religious, but mostly of the Protestant variety - only somewhere between 1-5% of the population identifies as Rastafarian). The locals speak patois as well as English. There is definitely a cultural difference between what Americans would consider polite and what the locals do, but it's easy enough to get used to - and once it's clear you're not just another asshole tourist, they're more friendly.
Our total cost for the vacation portion (read: non-wedding) was about $3300 (flights, hotel, taxis, non-hotel food, massage, excursion, souvenirs, etc). At least in the touristy areas, you can use Jamaican and American money interchangeably. They say the rate is 10 to 1, but it's actually 100 to 1 - 1000 Jamaican is 10 USD. We changed over about a third of our spending money into Jamaican. We also waited longer than we should have to buy our flights, which ended up costing us more than we planned - buy them early. Southwest also started flying in to Jamaica the day we left (we're pretty sure we saw the first plane come in), so there are probably cheaper options now than what we had. We decided to play it safe and get the CDC recommended shots beforehand, which was an additional $370 we didn't originally plan for.
To sum up: Jamaica is awesome and beautiful, and we are so glad we went.
p.s. I am working on a post on the wedding stuff for A Practical Wedding, and if they publish it I'll link to it here.