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.
Bartender, Jared Penrose and friends embarks on a new adventure of owning his own food truck. After encouraging his girlfriend Shevonne to pursue her music career, Jared finds an unexpected surprise waiting for him at home.
Sully treats everyone to a fun day on the water where he opens up to Jared about his marriage and announces a surprising career decision. During a night of celebrating, Naomi makes a shocking discovery.
Jared, Sully and Josh agree to go into business together and become the proud owners of a secondhand food truck. Naomi shares her broken heart with Iris who agrees to hire her at the coffee shop.
Seeing that Jared is feeling disconnected, Iris invites everyone to participate in a madcap adventure full of mystery. Sully and Josh introduce Jared to their new signature sandwich. The guys face a tragic setback in the light of day.
Jared and Sully take the truck out for a precarious test drive. Josh surprises everyone with an out-of-this-world design for the food truck. Jared's jealousy over a blossoming friendship becomes the final straw for the household.
The guys officially take The Grouper out on the road and become an immediate hit. It's a race against time as unforeseen events challenge Jared to make it to Shevonne's big concert.
As Jared tries to cope with Shevonne being gone, the group goes on a camping trip filled with kayaking, campfire stories and an intergalactic mission. Naomi helps for the first time with the food truck.
The fate of the food truck is in question as everyone weighs big life decisions during the holidays. Just as things are getting back to normal Jared has a life-changing reunion.