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After going through her divorce, Rose DiMico strikes it rich with penny stocks. Although she is financially secure, she still feels that there is something missing from her life. After purchasing a beautiful castle on the island of Capri in Italy, she recounts her struggles of developing the new property into a luxurious, five-star hotel and the excitement of her blossoming relationship with A-list actor, Leonardo Montague. Will she find true love on the 'Island of Love'?

Working for a travel agency, Marie's company sends her on a trip to Hawaii to learn about destination weddings and honeymoons on the beautiful island of O'ahu. At her first group meeting though, she encounters Matt, a past crush who happens to be engaged to Alex, the woman heading the Familiarization Trip. Struggling with her past feelings, flames ignite and the island will never be the same for her again.