| Description | Letter | City | % Correct |
|---|---|---|---|
| City near the above that is the namesake of an infamous U.S. military prison | G | Guantánamo | 100%
|
| The Spanish-American War began after the USS Maine blew up in this city's harbor | H | Havana | 100%
|
| Largest city on the northern coast of Jamaica | M | Montego Bay | 100%
|
| Located off the shore on Paradise Island is the Atlantis casino resort | N | Nassau | 100%
|
| Capital of Trinidad and Tobago | P | Port of Spain | 100%
|
| Oldest European city in the Americas, founded in 1498 by Bartholomew Columbus | S | Santo Domingo | 100%
|
| Was near the epicenter of an earthquake that killed over 200,000 people in 2010 | P | Port-au-Prince | 86%
|
| Its major airport is located on the exact opposite side of the island it is the capital of | R | Roseau | 86%
|
| Largest city on the southern coast of Cuba | S | Santiago | 86%
|
| Shares its name with the easternmost city in Canada | S | St. John's | 86%
|
| Birthplace of Robyn Fenty, better known as Rihanna | B | Bridgetown | 71%
|
| Capital of Saint Vincent and the Grenadines | K | Kingstown | 71%
|
| Capital of the French overseas region of Guadeloupe | B | Basse-Terre | 57%
|
| Capital of the Dutch island of Aruba | O | Oranjestad | 57%
|
| Resort town at the eastern tip of the Dominican Republic | P | Punta Cana | 57%
|
| A music video filmed here in 2017 surpassed Gangnam Style to become the most watched YouTube video | S | San Juan | 57%
|
| City in Puerto Rico named for the great-grandson of Spanish conquistador León | P | Ponce | 43%
|
| Martinique port city destroyed in the deadliest volcanic eruption of the 20th century | S | Saint-Pierre | 29%
|
| City on the island of Nevis where Alexander Hamilton was born | C | Charlestown | 14%
|
| Main settlement on the French half of Saint Martin | M | Marigot | 14%
|