The first photo of the getaway was shared by the 28-year-old singer on Sunday and finds her posing with friends inside a car. Pickler used the hashtags: #GirlsTrip and #IslandBabes to label the photo.
After the fact, the "Best Days of Your Life" singer has continued to document her outings and the blue skies that surround her on the image sharing site.
In the last picture of the bunch Pickler shows off her toned body in a bikini, sunglasses and a fedora as she holds a drink. She captioned the photo "#CabanaGirl ;)."