| Name | First Aired | Runtime | Image | |
|---|---|---|---|---|
| S14E01 | Raising A Family On St. John |
October 21, 2018
HGTV
|
25 | |
| S14E02 | A Flip Flop Island for Flip Flop People |
October 21, 2018
HGTV
|
25 | |
| S14E03 | Time To Relax On Roatan |
October 28, 2018
HGTV
|
25 | |
| S14E04 | Slowing Down On Aruba |
October 28, 2018
HGTV
|
25 | |
| S14E05 | Island Time, All The Time |
November 4, 2018
HGTV
|
25 | |
| S14E06 | Taking the Family to Turks and Caicos |
November 4, 2018
HGTV
|
25 | |
| S14E07 | Breaking a Sweat in Puerto Rico |
November 11, 2018
HGTV
|
25 | |
| S14E08 | Heading Home To St. Thomas |
November 11, 2018
HGTV
|
25 | |
| S14E09 | Sun and Serenity on Utila |
November 18, 2018
HGTV
|
25 | |
| S14E10 | Rediscovering on Barbados |
November 25, 2018
HGTV
|
25 | |
| S14E11 | Trading Cold for St. John Sun |
November 25, 2018
HGTV
|
25 | |
| S14E12 | Historic Move to San Juan, Puerto Rico |
November 25, 2018
HGTV
|
25 | |
| S14E13 | Building a New Life on St. Thomas |
March 10, 2019
HGTV
|
25 | |
| S14E14 |
Back to Barbados
season finale
|
March 24, 2019
HGTV
|
25 |
No artwork of this type.
No artwork of this type.
No artwork of this type.