Summer is coming to an end, and no doubt many are trying to squeeze in one last vacation or short getaway before fall. With personal holidays dominating our thoughts, it seems only fitting that National Aviation Day arrives Sunday. Established in 1939 to celebrate the birthday of aviation pioneer Orville Wright, National Aviation Day honors the technical and engineering advancements that have allowed many to experience new cultures and unusual locations around the globe. The gift of flight remains a wonder, enabling us to be somewhere else in just a few hours. No surprise, then, that travel continues to inspire many musicians. Some have simply been enamored by the splendor of aircraft, and others have used the possibilities of flight to detail more complex emotions. Here, we look at five of our favorite songs about flying.

Frank Sinatra, "Come Fly with Me"
Currently under construction at New York's John F. Kennedy International Airport is a hip, luxurious hotel that will reside in the space once occupied by TWA, an airline that throughout the 50s promoted flight as an extravagant indulgence. Frank Sinatra's "Come Fly with Me" is the musical equivalent of such a lifestyle. A symphonic number punctuated by excited horns, it dreams as much of fancy martinis in first class as it does mysterious locales. "If you can use some exotic booze, there's a bar in far Bombay," Sinatra sings with his signature grace. He isn't necessarily proposing sightseeing but pictures an endless honeymoon. At the time, he allegedly even remarked that the colorful drawing that doubles as the album's cover – Sinatra wearing a suit and standing on a runway – looked like an ad for TWA. (Note the logos and script on the airplanes.) Maybe, but if anyone can sell upper-class refinement and infinite leisure, it's Frank.

The Royal Guardsmen, "Snoopy vs. the Red Baron"
One could argue that two of the most famous pilots of the past 100 years are none other than Red Baron, a.k.a. ace WW1 German flyer Manfred von Richthofen, and Snoopy, the penciled and inked beagle from the "Peanuts" cartoon. Famously, "Peanuts" creator Charles M. Schulz penned strips in which Snoopy took on the fabled baron. And in 1966, second-rate Florida garage band the Royal Guardsmen had the goofy but clever idea to immortalize Snoopy's comic adventures as if he were a war hero. While the group's non-Snoopy British Invasion-inspired songs failed to garner much attention, "Snoopy vs. the Red Baron" remains a keeper. The chorus – "Ten, twenty, thirty, forty, fifty, or more" – is tailor-made for barroom sing-alongs and depicts the Royal Guardsmen counting off the Red Baron's fatal hits. In the background, we hear what's intended to be the shouts of American and German generals. The group also loads the novelty hit with jet sounds and exaggerated vocal breaks. And, nearly two minutes in, a keyboard-guitar shimmy quotes "Hang on Sloopy" for no apparent reason other than the word "sloopy" sounds like "snoopy." Ridiculous, sure, but dang if it isn't a blast.

Iron Maiden, "Empire of the Clouds"
Bruce Dickinson, lead singer of Iron Maiden, is known to some as Captain Dickinson. It's no mere nickname. Dickinson, an airline enthusiast, served as a commercial pilot with Astraeus Airlines for a number of years and now navigates his band around the world from the cockpit. So, when he sings "live to fly, fly to live" on Iron Maiden's "Aces High," he's not simply shouting a story about the Battle of Britain. He's expressing a way of life. The group's recent "Empire of the Clouds," at just over 18 minutes, not only serves as an epic metal suite but captures Dickinson's knowledge of aviation. With such detailed descriptions as as "her canvas skin, silvered in the sun," the song, inspired by the 1930 crash of Britain's R101 airship, gets relayed from the point of view of someone with a clear passion for history and engineering. "Dreams live on," Dickinson sings near song's end, but before we get that far, we're treated to a piano-led section that expands from precise, militaristic-like marching into majestic, symphonic guitar reveries. The R101 was thought once to be a work of perfect craftsmanship. Here, Iron Maiden attempts to match the airship's grandeur.

Ike Reilly, "Duty Free"
Under-appreciated Midwestern artist Ike Reilly has long melded rock and folk on a string of sharp politically minded albums. He's increasingly focusing on topical, acoustic-leaning songs, but his 2001 effort Salesman and Racists opts for an aggressive, guitar-focused route. The album's "Duty Free" is technically more about an airport than an airplane, but it still channels the sense of freedom – and joy of the unknown – that stems from air travel. Beginning with the low hum of an electric guitar, the tune takes off as Reilly details frustrations with a loved one, the country, and his own expectations. His destination remains unknown. We don't even know if he intends to run to the airport and buy a one-way ticket. Yet it all goes down as the ultimate grown-up daydream. "Do you need anything from duty free," he sings, his upper-register and scratchy voice practically begging for an affirmative answer to prod him to take to the sky.

The Supremes, "5:30 Plane"
The legendary Motown group was a bit removed from the top of the pop charts when, in the early 70s, it turned to arranger and composer Jimmy Webb for the album The Supremes Produced and Arranged by Jimmy Webb. An ace songwriter known more for classically styled orchestral arrangements than the passionate soul and R&B that marks much of the Supremes' best work, Webb failed to return the act to mainstream dominance. But the record, the last to feature Jean Terrell, who had replaced Diana Ross, contains a number of gems. Among them is "5:30 Plane," which spins the get-out-of-town idealism afforded by air travel into heartbreak. The slow ballad feels built for Broadway all the while the Supremes detail a relationship in shambles. "I didn't wanna be here, baby, when you got home," sings Terrell as background voices swell and envelop her like a hug. But the narrator indeed sits alone, dreaming of a life somewhere else led by wherever the early evening flight will take her.