Ambitious executive Dan Kinney arrives in Florida for business only to discover that his big financial investment has tanked, setting off alarm bells with his firm, family, and authorities. In denial and locked out of his accounts, Dan relies on travel points to stay at a posh beachside resort until the scandal blows over. He charms guests and irritates employees until a drunken outburst threatens to land Dan on the streets.

Desperate to fix his situation, Dan enlists a spy to uncover intel from his New York firm. Under strict rules from the hotel manager, he sneaks out to explore St. Pete/Clearwater. At the local aquarium, a sexy staff biologist enlists his help in a unique animal interaction.

As the SEC investigation intensifies, Dan is focused on following the money until bartender Jared enlists him for a geocaching challenge. While exploring St. Pete/Clearwater, Dan rediscovers his competitive side and an idea that may prove his innocence.

Eager to get his old life back, Dan attempts to meet up with a colleague at the hotel convention, but a mix-up at the bar has him chasing swag bags all over town. Dan runs into Amy at a local club before a revealing conversation with Stanford Demmings.

Dan and Jared's friendship continues to grow as Jared properly introduces Dan to the Blues. Listening to a local singer, Dan learns about Jared's war experience. Leaning into his depression, Dan inventories his situation, rations his points, and attempts to make amends.

After Dan apologizes to his estranged brother, Paul hits him up for babysitting his precocious niece and nephew while they're vacationing in Florida. Dan takes the kids to a Tampa Bay Rowdies' soccer game, where a childish prank results in panic, running from security and payback.

Dan discovers pregnant Maria crying over her wedding plans and enlists hotel staff - and the rest of his cash and the most of his remaining points - to rescue the nuptials The event takes an unexpected turn while crossing the Tampa Bay via the Cross Bay Ferry.

As the SEC investigation comes to a close and Dan Kinney's name is cleared, he is faced with a major life decision. As he seemingly makes his decision and moves ahead, he receives devastating news from his family that may again change everything.