In Road to Singapore, Bing Crosby plays Josh Mallon, a wealthy heir who has been disowned by his father for refusing to marry a woman he doesn't love. Bob Hope plays Ace Lannigan, Josh's best friend and partner in various unsuccessful business ventures. Both men decide to leave America and seek refuge in Southeast Asia, where they hope to find adventure and forget about their romantic troubles.
In Singapore, Josh and Ace meet Mima (Dorothy Lamour), a beautiful dancer who captivates them both. They compete for her affections, but Mima seems to prefer Josh. However, as they spend more time together, Mima reveals that she is on the run from her abusive fiancé, Caesar (Anthony Quinn), who wants to force her into marriage.
Josh and Ace decide to help Mima escape from Caesar and flee to a remote island, where they build a makeshift house and try to start a new life. However, their peace is soon disrupted by Caesar, who tracks them down and threatens to kill them all. In a daring escape, Josh, Ace, and Mima use a makeshift raft to sail to safety, while Caesar is left stranded on the island.
In the end, Josh and Ace decide to return to America, but not before Mima gives them each a necklace as a memento of their time together. As they board their ship, they sing a cheerful song about their adventures, promising to reunite with Mima one day. Road to Singapore was the first of seven "Road to" films starring Crosby, Hope, and Lamour.
