| 100% | KEYWEST | 7 | Florida island associated with Jimmy Buffett: 2 wds. |
| 48% | MARGARITA | 9 | Tequila-based drink associated with Jimmy Buffett |
| 43% | OLIVEDRAB | 9 | Green hue associated with military uniforms: 2 wds. |
| 39% | AMA | 3 | "Today I ___ man" (quote associated with bar mitzvahs): 2 wds. |
| 38% | WEEKENDUPDATE | 13 | Tina Fey's 9-Across segment with Jimmy Fallon: 2 wds. |
| 37% | SONYMUSIC | 9 | ___ Entertainment, music label which has been associated with artists like Alan Walker and Justin Bieber: 2 wds. |
| 36% | KEYWEST | 7 | Florida island where the Ernest Hemingway House is located (2 wds.) |
| 36% | VIRGINRECORDS | 13 | British record label founded by Richard Branson which has been associated with artists like David Guetta: 2 wds. |
| 36% | ELLIS | 5 | NYC island associated with immigration |
| 36% | JETLAG | 6 | Malady associated with flying across multiple time zones (2 wds.) |
| 35% | LOGCABIN | 8 | Dwelling place associated with Abraham Lincoln (2 wds.) |
| 35% | SICILY | 6 | European island associated with the prickly pear |
| 34% | ABC | 3 | Trio associated with 2 |
| 33% | RAPA | 4 | Half of the name of an island associated with heads |
| 33% | FLAMINGO | 8 | Bright pink bird associated with Florida |
| 33% | CABLEKNITSWEATER | 16 | Garment associated with the Aran Islands |
| 32% | ATE | 3 | What Jimmy Buffett did with his cheeseburger |
| 32% | CURACAO | 7 | Blue liqueur associated with a Caribbean island |
| 32% | SURVIVALOF | 10 | With 44-Across, phrase associated with 32-Across's evolutionary process: 2 wds. |
| 32% | EMO | 3 | Genre associated with the band Jimmy Eat World |
| 31% | ALAN | 4 | Country legend Jackson who sang "It's Five O'Clock Somewhere" with Jimmy Buffett |
| 31% | ASTO | 4 | With regards to: 2 wds. |
| 31% | ASFOR | 5 | With respect to: 2 wds. |
| 31% | INHORROR | 8 | With great fear: 2 wds. |
| 31% | ASIS | 4 | With no warranties: 2 wds. |
| 31% | ASIS | 4 | With no changes: 2 wds. |
| 31% | ASIS | 4 | With no warranty: 2 wds. |
| 31% | ASIS | 4 | With no modifications: 2 wds. |
| 31% | VEROBEACH | 9 | Coastal Florida town with a Disney Resort: 2 wds. |
| 31% | MIAMIHERALD | 11 | South Florida newspaper associated with a puzzle hunt |