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Two questions actually:

  1. Are US dollars widely accepted in Jamaica? For example if I'm in a small town buying a pack of gum, would they accept my US dollars?

  2. In Jamaica, do they refuse to accept your US dollars, if they don't look brand new and crisp, as is done in certain countries?

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tripadvisor.com/Travel-g147309-c140152/… may be helpful. –  choster Dec 9 '13 at 15:30
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2 Answers

As you can see on this very detailed report on Tripadvisor, it depends where you are and what you are trying to pay for. This by the way goes for any other place that is highly frequented by one specific nationality, such as Macau and HKG for Chinese currency, Switzerland for Euro etc:

Places frequented by tourists will accept USD. There is a chance that you will get change given in local currency. Exchange rates might be not as favorable as at a bank. So you pack of gum depends on the question if it's at a kiosk next to the place where Bob Marley was born? Likely yes. If it's from the street vendor in a place where they only see a foreigner once a quarter? Likely not. Unless, of course, you are willing to pay 15USD for that pack of gum, of course.

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(Asker here; I have just returned from my trip to Jamaica.)

1) In the touristy spots - Montego Bay, Negril, Ocho Rios, you will generally have no problem paying in USD.

I am not sure however about the less touristy spots, because by the time I got to such spots, I already had the opportunity to change my USD into JMD.

Which is what you want to do anyway because vendors accepting USD will usually give you a bad rate. For example in Dec 2013 one could get 103.5 JMD per USD at most cambios, and sometimes even 104 JMD per USD, but when accepting USD they generally used the rate 1 USD = 100 JMD.

2) Nobody ever had any problem with any of my USD notes being old, crumpled, dirty, etc. USD coins do not seem to be accepted though.

Misc advice: Do NOT exchange your money at the MoBay airport, where the rates are nothing short of a colossal scam (something like 1 USD = 86 JMD even though the outside standard rate was 103.5).

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