I don't travel much, but most island experiences are very Disney like, as in if you go to a big resort at a popular destination, you will be isolated from the rest of the civilization on the island. In those cases, you had best be vacationing strictly for the "spa" experience more or less. Only an opinion.
If you are like pray, wandering off the resort can be dangerous, especially if you go chasing Jamaicans, or wander off into employment situations on party islands.
Why not go to an italy (never been), or a greece (never been), or someplace that has major urban centers? Spain looks awesome to me. Cuba is a really popular place, and cheap, but if you are inside the USA, I think it is illegal for you travel there, I am not sure entirely.
These places are English speaking islands in the Caribean according to the wiki... English (official language of Anguilla, Antigua and Barbuda, Bahamas, Barbados, British Virgin Islands, Cayman Islands, Dominica, Grenada, Jamaica, Montserrat, Puerto Rico, Saba, St. Eustatius, St. Kitts and Nevis, St. Lucia, St. Maarten, St. Vincent and the Grenadines, Trinidad and Tobago, Turks and Caicos Islands, U.S. Virgin Islands)
Here are english speaking countried in the pacific. Obviously airfare is a bigger issue in some cases. Australia American Samoa Cook Islands
Fiji Guam Kiribati
Marshall Islands Micronesia (Fed. States of) Nauru
New Zealand Niue Northern Mariana Islands
Palau Pitcairn Samoa
Solomon Islands Tonga Tuvalu
Vanuatu
Anyways, where ever you decide to go, search for travel advisories provided by the government. For instance, in Jamaica you don't want to go into Kingston. I'd guess you'd be safe in Montego Bay if you were careful, but I've never been. I believe specifically you want to avoid west kingston - http://en.wikipedia.org/wiki/Yardie Personally I think Jamaicans are super laid back, you just probably want to mind your own business.
http://travel.gc.ca/destinations/jamaica
Violent crime (armed robbery, murder) and petty theft (pickpocketing, bag snatching) occur, particularly in Kingston, Spanish Town and in Montego Bay. Although the presence of security and anti-crime troops has intensified in major urban areas, drug- and gang-related violence, including shootings, continues to be a significant problem and can result in death, injury and destruction of property. There is a constant risk of becoming the victim of crossfire. Police may impose curfews with short notice in areas where gang activity is a concern. Maintain a high level of personal security awareness at all times, follow the advice of local authorities and monitor local media.
If you go to Mexico, ideally, you want to avoid the border, and south western states.
http://travel.gc.ca/destinations/mexico
Northern states (see Advisory)
Shootouts, attacks and illegal roadblocks may occur without warning. Criminals especially target sport utility vehicles and full-size pickup trucks for theft and carjacking along highways. Avoid inter-city road travel in the northern states.
Travel to and within Ciudad Juarez poses particular challenges and requires extreme caution.
Exercise a high degree of caution when travelling in the city of Monterrey, avoid movement after dark and stay within the suburb of San Pedro Garza GarcÃa.
South-Western states (see Advisory)
Criminal activity has significantly increased in the states of Jalisco, Guerrero and Michoacán. Illegal roadblocks and demonstrations have been reported on a more frequent basis. The deterioration of the security situation is particularly noticeable in the rural areas of Guerrero and Michoacán. The rapid expansion of vigilante militias is troubling, and there have been instances where such groups have fired at vehicles that did not adhere to their roadblocks.
And you never want to go to Iran, period...
http://travel.gc.ca/destinations/iran
Violent crime affecting both Iranians and foreigners has increased. Petty theft occurs. Do not show signs of affluence. Ensure personal belongings, passports and other travel documents are secure, and carry a photocopy of your passport’s identification page at all times.
Watch for fraudulent plainclothes police officers who may ask to see foreign currency and passports. If you are approached, politely decline to cooperate but offer to go to the nearest police station.
Where ever you go though, if it is a poor country and you are white, you will want to stay away from purchasing things that are not displayed in a store with a price tag. Only my opinion... I mean you can, but you will be paying too much obviously and in some cases you will become a regular client whether you want to be or not.