After serving in the military for nine years, Josh has had a difficult time re-adjusting to life back home. He was able to find his place in the world again after meeting the love of his life, Alejandra, whom he nominates for a vacation for helping him through such a tough time. On a voyage in the Caribbean, Tommy and Andrea arrange an exploration of historic Cartagena, Colombia, in Alejandra’s home country. Then, they discover the magical island of Eleuthera, Bahamas where Josh proposes a life changing surprise at Princess Cays.