Constructed around a light-hearted travel theme, Come Fly With Me, Frank Sinatra's first project with arranger Billy May, was a breezy change of pace from the somber Where Are You. From the first swinging notes of Sammy Cahn and Jimmy Van Heusen's "Come Fly With Me" -- which is written at Sinatra's request -- it's clear that the music on the collection is intended to be fun. Over the course of the album, Sinatra and May travel around the world in song, performing standards like "Moonlight in Vermont" and "April in Paris," as well as humorous tunes like "Isle of Capri" and "On the Road to Mandalay." May's signature bold, brassy arrangements give these songs a playful, carefree, nearly sarcastic feel, but never is the approach less than affectionate. In fact, Come Fly With Me is filled with varying moods and textures, as it moves from boisterous swing numbers to romantic ballads, and hitting any number of emotions in between. There may be greater albums in Sinatra's catalog, but few are quite as fun as Come Fly With Me.
AllMusic Review by Stephen Thomas Erlewine