By Tour Name | By Year | By Venue | By City | By Country/State
Shows by City: Key West
| Show Date | Venue | City | State | Tour Name | |
| 02-11-2023 | Coffee Butler Amphitheater | Key West | FL | Second Wind Tour – 2023 | |
| 02-09-2023 | Coffee Butler Amphitheater | Key West | FL | Second Wind Tour – 2023 | |
| 02-06-2023 | Key West Theater | Key West | FL | Second Wind Tour – 2023 | |
| 02-04-2023 | Key West Theater | Key West | FL | Second Wind Tour – 2023 | |
| 11-05-2015 | Casa Marina | Key West | FL | Workin’ and Playin’ Tour | |
| 04-01-2015 | San Carlos Institute Theatre | Key West | FL | ||
| 11-04-2011 | Margaritaville Street Festival | Key West | FL | ||
| 02-12-2009 | Margaritaville Cafe Key West | Key West | FL | Special show for employees | |
| 01-28-2005 | Margaritaville Cafe | Key West | FL | 20th Anniversary | |
| 11-04-2004 | Margaritaville Street Festival | Key West | FL | Meeting of the Minds | |
| 12-05-2003 | Margaritaville Cafe | Key West | FL | Special Apperance | |
| 11-01-2002 | Margaritaville Street Festival | Key West | FL | Meeting of the Minds | |
| 10-31-2002 | Margaritaville Cafe | Key West | FL | Surprise appearance | |
| 11-07-1998 | Margaritaville Street Festival | Key West | FL | ||
| 10-03-1992 | Margaritaville Cafe | Key West | FL | ||
| 10-26-1991 | Margaritaville Cafe | Key West | FL | Impromtu shows Smathers Beach & Margaritaville | |
| 06-21-1988 | Margaritaville Cafe | Key West | FL | ||
| 11-28-1987 | Wickers Field | Key West | FL | A Pirate Looks At Forty Tour | |
| 10-27-1986 | Del Rios Grill | Key West | FL | Benefit to save the Salt Ponds | |
| 12-18-1977 | Mallory Square | Key West | FL | Changes in Latitudes, Changes in Attitudes | |
| 07-28-1977 | The Blue Moon Saloon | Key West | FL | 1977 Tour | |
| Number of Shows: 21 | |||||