| #8802, aired 2023-02-07 | HOLIDAYS AROUND THE GLOBE $400: The first Monday in July is Caricom Day, observed in Barbados, Jamaica & other countries; the "Cari" is for this geographic feature the Caribbean |
| #8325, aired 2021-01-29 | AROUND THE CARIBBEAN $400: Major towns in this Caribbean nation include Jacmel, Pétion-Ville & Port-de-Paix Haiti |
| #8325, aired 2021-01-29 | AROUND THE CARIBBEAN $800: The largest range in Jamaica, these mountains are famous as a source of coffee beans the Blue Mountains |
| #8325, aired 2021-01-29 | AROUND THE CARIBBEAN $1200: The easternmost of Cuba's 15 provinces is this single-named one near where the U.S. maintains a military base Guantanamo |
| #8325, aired 2021-01-29 | AROUND THE CARIBBEAN $1600: Boulders form secluded pools at the Baths, a beach area in this colony of the queen the British Virgin Islands |
| #8325, aired 2021-01-29 | AROUND THE CARIBBEAN $3,000 (Daily Double): 2 capital cities are located on this Caribbean island: Marigot, which is French, & Philipsburg, which is Dutch St. Maarten |
| #8119, aired 2019-12-19 | AROUND THE WORLD $600: The only land border between the Netherlands & France is on this 34-square-mile Caribbean island split between them Saint Martin |
| #7831, aired 2018-10-01 | AROUND THE CARIBBEAN $400: White sand beaches are an attraction of this "A" of the Caribbean's ABC islands Aruba |
| #7831, aired 2018-10-01 | AROUND THE CARIBBEAN $800: The Windward Passage separates Haiti from this country to the northwest Cuba |
| #7831, aired 2018-10-01 | AROUND THE CARIBBEAN $1200: You'll find Cockpit Country, named after a rooster fighting term, near Montego Bay in this nation Jamaica |
| #7831, aired 2018-10-01 | AROUND THE CARIBBEAN $1600: This 5-letter Panamanian city sits on Limón Bay near the Caribbean entrance to the canal Colón |
| #7831, aired 2018-10-01 | AROUND THE CARIBBEAN $2000: An 1850 treaty averted a crisis between the U.S. & Britain over this Nicaraguan coast, among other territories the Mosquito Coast |
| #6241, aired 2011-11-07 | THE CARIBBEAN $1000: You might see Oscar de la Renta around Punta Cana, on the eastern tip of Hispaniola in this country the Dominican Republic |
| #5116, aired 2006-12-04 | "J" WALKING $500 (Daily Double): The original pirates of the Caribbean, possibly including Henry Morgan, seized this island around 1655 Jamaica |
| #4830, aired 2005-09-16 | AROUND THE WORLD $2000: The tallest bridge in the Caribbean is the Queen Juliana Bridge in this capital of Curacao Willemstad |
| #4036, aired 2002-03-04 | AROUND THE WORLD $400: If Angelique sang "Dominique" on Martinique, she'd be in this sea the Caribbean |
| #3117, aired 1998-03-03 | AROUND THE WORLD $1000: Some cyclists take a downhill bicycling tour of this Caribbean country's Blue Mountains Jamaica |
| #3096, aired 1998-02-02 | AROUND THE WORLD $1000: The Tortola Museum of these British Caribbean islands is in Road Town, the capital British Virgin Islands |
| #2878, aired 1997-02-19 | SHOPPING AROUND THE WORLD $400: Plaza Las Americas in this U.S. commonwealth is the largest shopping mall in the Caribbean Puerto Rico |
| #2549, aired 1995-10-05 | AROUND THE WORLD $1000: You can rent princess Margaret's villa on Mustique, an island in this sea, for about $6,000 a week the Caribbean |
| #2295, aired 1994-07-22 | AROUND THE WORLD $300: These Caribbean islands are sometimes called the B.V.I. for short the British Virgin Islands |
| #1799, aired 1992-05-28 | AROUND THE WORLD $200: Anguilla & Antigua are in this sea the Caribbean |
