 Andy Bernard ( Ed Helms ) learns that his father took all the family money and fled to Argentina with his mistress . Left to pick up the pieces , Andy sells off family heirlooms , and is upset that he has to sell the family boat for lack of any other means for his mother to support herself . Erin Hannon ( Ellie Kemper ) convinces him that before he sells the boat , they should take it out for one last sunset cruise , and they drive to Stamford , Connecticut , where the boat is docked . Andy starts to hoist the main sail , but is stopped by a broker who is to sail it to the Caribbean for the buyer . With Erin 's encouragement , Andy decides to take the boat to the Caribbean himself . He then finds his drunken brother Walter ( Josh Groban ) passed out in the liquor closet . Walter comes to and tells Andy he wanted to get the first relapse out of the way before checking into rehab . Andy invites him on the trip , saying they both need family time together and leaves , thanking Erin for her encouragement . Erin says to the camera that she would have loved to go with him if he asked . Back in the office that evening , Pete ( Jake Lacy ) asks Erin to join him for drinks , and she accepts . 
