The Travel Air 5000 was an early high-wing monoplane airliner and racing monoplane designed by Clyde Cessna and is chiefly remembered for being the winner of the disastrous Dole Air Race from California to Hawaii.

A second aircraft was built that December, and featured a Wright J-4 Whirlwind as the Travel Air 5000.

The Dole racers were modified with 425-gallon fuselage fuel tanks and earth inductor compasses.

The prototype Travel Air 5000, s/n 160 "The Spirit of Oakland" was originally sold to Pacific Air Transport in April 1927 and then resold to Ernest Smith for a 14 July flight from Oakland, California, to Molokai, Hawaii, where it crashed on landing becoming the second aircraft to complete a trans-pacific flight, and the first civilian aircraft to do so.

On 30 June 1927 production of two Modified model 5000's started in the newly constructed East Central factory.