When Sarah Wilson is named the new commander of a difficult military unit in Chioggia, Italy, she uproots her wife Maggie and teenage son Fraser to start a new chapter in this unfamiliar seaside town. Fraser longs for Mark, a friend he left behind in New York, and seems uninterested in connecting with the other teenagers on base – until he meets Caitlin.

The arrival of Caitlin's period accelerates her secret desire to experiment with her gender expression--and to flirt with girls, test boundaries with her boyfriend Sam, and spar with her father Richard. Later, Fraser discovers Caitlin's secret, which forever changes the nature of their relationship.

A fracture begins to form within the friend group following Caitlin and Sam's breakup. Maggie attends the Chioggia Festival with the neighborhood women and finds an unexpected companion. Meanwhile, the progress Colonel Wilson has made in her new role is derailed when she decides to deploy her troops early--and her complex relationship with Fraser is rattled.

With his deployment timeline fast-tracked, Craig spontaneously proposes to his Italian girlfriend, Valentina. Determined to ship him off with a celebration he'll never forget, his friends pool their resources for a Hawaiian-themed wedding that leads to an evening of debauchery.