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Answer:
CUBA
Possible Questions:
Caribbean island
World Baseball Classic team
___ libre
Havana's home
Caribbean country
Morro Castle site
Island in the West Indies
Largest Caribbean island
Desi's homeland
Columbus landfall of 1492
Castro's country
Sierra Maestra country
San Juan Hill site
San Juan Hill locale
Onetime Hemingway home
It's south of Florida
Havana's land
Guantanamo Bay locale
Castro's land
Castro's home
Bay of Pigs location
Bay of Pigs locale
Actor Gooding Jr.
Where the conga originated
Where Guantanamo Bay is
West Indies' largest island
View from Guantanamo Bay
Tom's "Jerry Maguire" co-star
Sugar producer
Source of contraband cigars
San Juan Hill setting
Neighbor of the Keys
Manzanillo's island
Largest island on the Caribbean
Largest island in the West Indies
Land claimed by Columbus
Island country near Key West
Havana is its capital
Guantanamo Bay island
Florida's neighbor
Embargoed land
Desi Arnaz's birthplace
Castro's place
"Pearl of the Antilles"
Where to find Guantánamo
Where the rumba originated
Where many Miamians were born
War zone of 1898
Tom's "Jerry Maguire" costar
Tobacco-exporting country
Sugar island
Skyjackers' mecca
Site of Guantánamo Bay
Site of Guantánamo Bay
Site of 1962 Kennedy-Khrushchev confrontation
Setting for part of the documentary "Sicko"
Santiago de ___
San Juan Hill's locale
San Juan Hill country
Runner-up to Japan in the first World Baseball Classic
Raul Castro's country
Part of the Greater Antilles
Morro CastleÂ’s home
Major source of baseball talent
Major exporter of nickel
Locale of Guantánamo Bay
Largest of the West Indies
Largest of the Greater Antilles
Largest country in the Caribbean
Land south of Key West
Jamaica neighbor
It's east of Yucatán
Island where the daiquiri was invented
Island sometimes called El Cocodrilo
Island of the Greater Antilles
Island north of the Caymans
Island near Florida
Island named for its shape
Isla de Pinos site
International baseball powerhouse
Home to Morro Castle
Home of Guantanamo Bay
Havana's locale
Havana's island
Havana's country
Haiti's neighbor
Guantanamo locale
Godfather Part II setting
Gloria Estefan's birthplace
Gitmo's home
Fidel's realm
Fidel's land
Embargoed country
Elián Gonzalez's home
Destination of many 1960s-'70s airplane hijackings
Desi Arnaz's homeland
Country with the most all-time medals in Olympic baseball
Country where the Buena Vista Social Club is from
Country suspended from the Organization of American States in 1962
Country south of Florida
Castro's realm
Cask, in Córdoba
Camagüey's island
Camagüey's country
Bay of Pigs site
Arnaz's birthplace
Actor Gooding
A discovery of 1492
A discovery in 1492
A 1492 find
A 1492 discovery
2006 World Baseball Classic runners-up
1962 crisis area
1950s coup site
1492 discovery
"The Pearl of the Antilles"
___ sugar (lump for Castro?)
___ libre, rum drink
___ libre (rum drink)
___ libre (cocktail)