| 2025-09-07 | Where Gloria Estefan was born |
| 2023-04-07 | Title city in a 2017 #1 hit by Camila Cabello |
| 2022-09-22 | Where Hemingway worked on "For Whom the Bell Tolls" |
| 2022-05-02 | Capital of Cuba |
| 2018-09-16 | Where Hemingway wrote "The Old Man and the Sea" |
| 2018-05-27 | The U.S.S. Maine sank in its harbor |
| 2017-03-27 | Cuba's capital |
| 2016-11-05 | Premium cigar |
| 2015-09-06 | Caribbean capital |
| 2014-07-20 | World capital where Monopoly is banned |
| 2013-04-12 | Home of the Karl Marx Theater |
| 2013-01-13 | Where Ponce de León died |
| 2011-06-30 | Good smoke |
| 2011-04-12 | Hard-to-get cigar |
| 2009-04-24 | Plaza de la Revolución locale |
| 2001-06-04 | Capital on the Florida Strait |
| 2000-05-05 | Good smoke |
| 1999-11-27 | "Guys and Dolls" locale |
| 1999-03-05 | Plaza de la Revolución locale |
| 1998-10-25 | Esteemed smoke |
| 1998-09-15 | Castro's capital |
| 1997-12-23 | Harbor where the Maine blew up |
| 1997-07-13 | Humidor item |
| 1996-10-19 | Where Ponce de Leon died |
| 1996-10-15 | Chief port of the West Indies |
| 1996-04-29 | Hijacker's destination, once |
| 1995-07-16 | Caribbean capital |
| 1995-05-07 | Morro Castle site |