When referring to the Bay of Pigs prisoner release flight, the cabin crew state the plane used was a DC-6, however, the plane used for the evacuation scene was actually a DC-7.
The vehicles parked on the street are too new for 1963, specifically a 1964 Chevrolet Biscayne sedan (seen very often), a 1966 Pontiac Tempest sedan and a 1966 Lincoln Continental.
Dean and Collette discuss the movie "Barefoot in the Park". That wasn't released until 1967, years after this story takes place in 1963.