The staff of TGS suffers from winter blues. To try to cheer them up, Pete and Liz appeal to Jack to take the cast on a road trip to Miami in a clever “Miami = Synergy” pitch.
Jack loves the idea, but instead of Miami, he determines that they’ll be going to Boston, largely because of the fact that Nancy, his high school crush, lives there.
This totally ruins the idea of trying to beat the winter since it’s even colder in Boston than in New York, naturally.
When they arrive in Boston, adjustments are hard for much of the cast and writers, but Jack settles right in with a replica of his office waiting for him.
She soon admits that her husband left her to go to New Orleans and she doesn’t know what step to take next.
Liz tries to raise the spirits of the staff by encouraging them to see Boston. However, only Tracy accompanies her on a tour of the city where he promptly gets into a shouting match with men dressed up as the Founding Fathers.
Liz must find a scapegoat for all of their problems who she names as a major employee at NBC, Dale Snitterman. The only problem with this is that Snitterman is actually a real person at the office in Boston.
Meanwhile, Jack has come up with his own genius plan to help Nancy move on - convincing TGS cast members to go to her open house and pretend as if they’re interested in buying it.