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I retired to Jamaica as my wife is Jamaican and it was relatively easy to live here as the husband of a returning resident. Once you have hurdled the formalities the rest if plain sailing. I eventually requested permanent residence  status and that is the most arduous bureaucratic experience ever and they charged me $100,000 for the pleasure but at least I don't have to get my passport stamped every three years.
Medical care is relatively good providing you have insurance or deep pockets. My wife has a long term condition and the care she gets is on par with that she would get in the UK..and she sees the consultant at the time given on the dot so can't be too bad. Medicines are pricey and not all insurance policies cover everything so be warned. Be wary of being dumped onto the medical conveyor system as there does appear to be a habit of doctors passing you about and all that does is ring up the money.
The banks are efficient but they are all very very slow so take water and sandwiches if you have a lot of business to do.
I like the country as the weather is great, the people are friendly and I feel freer and less 'observed' than I ever was in the UK. There is less of the 'big brother' mentality here.
The downsides? Well don't move here if you just have to have a constant 100% supply of electricity as that just won't happen. I live in a tourist area and the power vanishes at least 10 times a year for varying amounts of time. Do not expect any warnings or apologies. That just does not happen.
Water supply comes and goes. The water pressure is variable so taking long showers (if you like that sort of thing) can be even longer than you think.
Phone, cable tv and internet is done mainly by Flow (Digicel have just started but they are only in Kingston and Portmore and may take years to get around the island). If anyone has ever dealt with Virgin cable in the UK then imagine that but 1000 times worse and that is Flow. Customer service sounds nice but is poor and you can wait hours (yes hours) to get a reply. They charge a fortune but most of the channels they provide are ones they are stealing from the US so they will go soon and we will be left with a rather odd ensemble of channels. The picture quality on their HD system  varies from pretty poor to so terrible you cannot watch it. The internet speed will never reach the speed they promise (same as virgin media) and they have a habit of also cutting everything off (without any warning or apology) for hours at a time. Don't fall into the trap that if get an internet TV you will be able to watch streaming from elsewhere cos you will not have the bandwidth and the buffering will drive you mad. If you can live with all that then Jamaica is great place to retire to.

For USA citizens who are curious to know about their social security benefits while living in Jamaica, here is an update from the US Embassy in Jamaica.

SOCIAL SECURITY VISIT

Social Security Benefits?  Payments?  Checks?  Disability?

Recent changes caused the elimination of Social Security appointment hours at U.S. Embassy Kingston, however representatives from the Regional Federal Benefits Office (RFBO) will be in Kingston on Wednesday, October 25 and Montego Bay on Thursday, October 26 to answer your social security questions!  Please come and visit us:

KINGSTON
Wednesday, October 25
8:00 a.m. – 12:00 p.m. and 1:00 p.m. – 4:00 p.m.
Walk in appointments welcome

MONTEGO BAY
Thursday, October 26
9:00 a.m. – 12:00 p.m. and 1:00 p.m. – 4:00 p.m.
Appointments can be made via phone 953-0620 or email MobayACS@state.gov

For further information:

·   See the Department of State’s travel website for the Worldwide Caution, Travel Warnings, Travel Alerts, and Country Specific Information for Jamaica and the Cayman Island.

·   Enroll in the Department of State’s Smart Traveler Enrollment Program (STEP) to receive security messages and make it easier to locate you in an emergency.

·   The U.S. Embassy in Jamaica is located at 142 Old Hope Road in the Liguanea area of Kingston, telephone (876) 702-6450, after hours emergency line at (876) 702-6000, and email at KingstonACS@state.gov.  The U.S. Consular Agency in Montego Bay is located at Whitter Village, Ironshore, telephone (876) 953-0620, and email MobayACS@state.gov.   The U.S. Consular Agency in the Cayman Islands is located at 202 B Smith Road Center, 150 Smith Road, George Town, telephone (345) 945-8173, and email at CaymanACS@state.gov.

·   Call 1-888-407-4747 toll-free in the United States and Canada or 1-202-501-4444 from other countries from 8:00 a.m. to 8:00 p.m. Eastern Standard Time, Monday through Friday (except U.S. federal holidays).

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