TOO COOL! Where can you find the Florida Keys largest smiley face? I’ve got the information right here to solve your curiosity. I’ve seen VERY large smiley faces painted on several cities water towers and many painted on the sides of buildings across the country… but never have I seen one painted on the roof of a houseboat! Take a few minutes and stop to see this one-of-a-kind spectacle. Parking is FREE and browsing around is well worth the time! Located on US-1 South at the Historic Charterboat Row & Key West City Marina about a mile or two down the road once you’ve actually arrived on the island of Key West.