CNN has an interactive guide to viewing the solar eclipse. Based on their map, the closer you are to their “blue line,” the higher the chances of you seeing a total eclipse.
75 and 90% chance of seeing a total eclipse:
The Bahamas
Turks and Caicos Islands
Dominican Republic
British Virgin Islands
Montserrat
50 to 75% chance:
Cuba
Cayman Islands
Jamaica
St. Lucia
Barbados
Grenada
Haiti
Aruba
Curacao
Trinidad and Tobago
Source: CNN