| Caribbean country | 17 |
| Morro Castle site | 17 |
| Island in the West Indies | 25 |
| Largest Caribbean island | 24 |
| Desi's homeland | 19 |
| Columbus landfall of 1492 | 25 |
| Castro's country | 20 |
| Sierra Maestra country | 22 |
| San Juan Hill site | 18 |
| San Juan Hill locale | 20 |
| Onetime Hemingway home | 22 |
| It's south of Florida | 25 |
| Havana's land | 17 |
| Guantanamo Bay locale | 21 |
| Castro's land | 17 |
| Castro's home | 17 |
| Bay of Pigs location | 20 |
| Bay of Pigs locale | 18 |
| Actor Gooding Jr. | 17 |
| Where the conga originated | 26 |
| Where Guantanamo Bay is | 23 |
| West Indies' largest island | 31 |
| View from Guantanamo Bay | 24 |
| Tom's "Jerry Maguire" co-star | 43 |
| Sugar producer | 14 |
| Source of contraband cigars | 27 |
| San Juan Hill setting | 21 |
| Neighbor of the Keys | 20 |
| Manzanillo's island | 23 |
| Largest island on the Caribbean | 31 |
| Largest island in the West Indies | 33 |
| Land claimed by Columbus | 24 |
| Island country near Key West | 28 |
| Havana is its capital | 21 |
| Guantanamo Bay island | 21 |
| Florida's neighbor | 22 |
| Embargoed land | 14 |
| Desi Arnaz's birthplace | 27 |
| Castro's place | 18 |
| "Pearl of the Antilles" | 33 |
| Where to find Guantánamo | 27 |
| Where the rumba originated | 26 |
| Where many Miamians were born | 29 |
| War zone of 1898 | 16 |
| Tom's "Jerry Maguire" costar | 42 |
| Tobacco-exporting country | 25 |
| Sugar island | 12 |
| Skyjackers' mecca | 21 |
| Site of Guantánamo Bay | 25 |
| Site of Guantánamo Bay | 29 |
| Site of 1962 Kennedy-Khrushchev confrontation | 45 |
| Setting for part of the documentary "Sicko" | 53 |
| Santiago de ___ | 15 |
| San Juan Hill's locale | 26 |
| San Juan Hill country | 21 |
| Runner-up to Japan in the first World Baseball Classic | 54 |
| Raul Castro's country | 25 |
| Part of the Greater Antilles | 28 |
| Morro CastleÂ’s home | 23 |
| Major source of baseball talent | 31 |
| Major exporter of nickel | 24 |
| Locale of Guantánamo Bay | 27 |
| Largest of the West Indies | 26 |
| Largest of the Greater Antilles | 31 |
| Largest country in the Caribbean | 32 |
| Land south of Key West | 22 |
| Jamaica neighbor | 16 |
| It's east of Yucatán | 27 |
| Island where the daiquiri was invented | 38 |
| Island sometimes called El Cocodrilo | 36 |
| Island of the Greater Antilles | 30 |
| Island north of the Caymans | 27 |
| Island near Florida | 19 |
| Island named for its shape | 26 |
| Isla de Pinos site | 18 |
| International baseball powerhouse | 33 |
| Home to Morro Castle | 20 |
| Home of Guantanamo Bay | 22 |
| Havana's locale | 19 |
| Havana's island | 19 |
| Havana's country | 20 |
| Haiti's neighbor | 20 |
| Guantanamo locale | 17 |
| Godfather Part II setting | 25 |
| Gloria Estefan's birthplace | 31 |
| Gitmo's home | 16 |
| Fidel's realm | 17 |
| Fidel's land | 16 |
| Embargoed country | 17 |
| Elián Gonzalez's home | 28 |
| Destination of many 1960s-'70s airplane hijackings | 54 |
| Desi Arnaz's homeland | 25 |
| Country with the most all-time medals in Olympic baseball | 57 |
| Country where the Buena Vista Social Club is from | 49 |
| Country suspended from the Organization of American States in 1962 | 66 |
| Country south of Florida | 24 |
| Castro's realm | 18 |
| Cask, in Córdoba | 19 |
| Camagüey's island | 24 |
| Camagüey's country | 25 |