The oil painting "Le Marin" depicts a sad-looking man dressed in a blue and white striped sailor's shirt sitting on a chair.
"You have ... a slightly dark sense around the picture. It's nervous, it's on edge and slightly gloomy," said Conor Jordan, deputy chairman of impressionist and modern art at Christie's.
The 130 by 81 centimetre (52 by 31 inch) vertical painting shows the man resting his head against his right hand, while his legs are crossed with his left hand on his knee.
"That's a traditional symbol of melancholy," Jordan added.
Created in 1943, during the Nazi occupation of France, the painting reflects the distress and anxiety of the Spanish painter who was under threat of being sent to a concentration camp in Germany.
Le Marin's last appearance was 21 years ago at an auction of works from the collection of New York art collectors Victor and Sally Ganz.
The painting will be on view in Hong Kong until April 3 before travelling to London and then New York, where it will go under the hammer on May 15 as part of Christie's Impressionist and Modern Art sale.
Le Marin is one of the five most important pieces by Picasso, according to Christie's.
Last November, a series of 100 Picasso etchings which deal with his erotic obsessions and marital strife, as well as political turmoil in the 1930s, sold for 1.9 million euros (US$2.2 million) in Paris to an unnamed American collector.
Picasso's "The Women of Algiers (Version 0)" set a world record as the most expensive piece of art sold at auction when it fetched $179.4 million at Christie's in New York in 2015.
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