This is information for each country regarding American visa requirements for all countries in the Caribbean. This is current from the State Department as of September 2016.
Bahamas: No visa required.
Turks and Caicos: No visa for less than 90 days. Visas required for longer stays and is renewable once.
Cuba: Visa required. Initial 30 day stay, renewable once for 30 days. Travel is only permitted for 1 of 12 reasons as listed by the US Government. We are looking for legitimate, reasonably priced Cuban travel operators and will update this page when we have found one we would use.
Cayman Islands: No visa required.
Jamaica: No visa required.
Haiti: No visa for less than 90 days.
Dominican Republic: No visa required, but a tourist card ($10) must be purchased before or on arrival. Tourist card covers up to 60 days.
British Virgin Islands: No visa required for less than 30 days.
Bonaire St, Eustatius, and Saba: No visa required for less than 90 days.
St Kitts and Nevis: No visa required for less than 90 days.
Anguilla: No visa required if you can show proof of accommodation, onward ticket (for some point in the future), and proof of funds.
Sint Maarten: No visa required for less than 90 days.
Antigua and Barbuda: No visa required if you can show proof of accommodation, onward ticket (for some point in the future), and proof of funds.
Montserrat: No visa required.
Guadeloupe, Barbados, Martinique (Collectively the French West Indies): No visa required for less than 90 days so long as you can show proof of accommodation, onward ticket and proof of funds.
Dominica: No visa required for less than 180 days (6 months).
St Lucia: No visa required if you can show proof of accommodation, onward ticket (for some point in the future), and proof of funds.
St Vincent and the Grenadines: No visa required.
Every Country Couple 
Valuable info! Thanks!!
Just glad to see Cuba becoming more accessible even if there are still hoops to jump through!