Although she has traveled all over the world, flight attendant Montana Moore has yet to find a man with whom she wants to settle down. However, with her sister's upcoming wedding and pressure from her oft-married mother, she's determined to get engaged in the next 30 days. In that time, her best friends (and fellow flight attendants) conspire to help her re-encounter her exes as she flies all over the country.
As four lifelong friends, Will, Bryan, Matt, and Corey, are on the road trip they've been planning their whole lives, Corey's beloved grandfather unexpectedly dies. When going to claim Corey's inheritance, the gang meets Matt's beautiful cousin Jessie and embark on a hilarious, extreme sports-filled adventure.
