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A Gentleman out for a curious sail. Peter Halkett sailing his first invention, an inflatable boat that could be deflated and used as a raincoat. The paddle became a walking stick; the sail an umbrella. Halkett’s boat attracted widespread interest in the 1840s. Halkett’s ingenious invention...

I've always thought that some of the best commerical art of the 20th century was cover art on plastic model boxes. One of the reasons for that is Roy Cross. ROY CROSS Roy Cross (b. 1924) was born in the Docklands of London, England. He first became known as an aviation artist and author, and...

Paul Signac, his slow ascent into pointillism. Along with Serat, he defined this impressionist technique. He had a soft spot for painting sailboats, harbors and sunsets -- ideally, and when happiest, all three. Le Clipper, Asnieres, 1887 Evening Calm, Concarneau, 1891 The port at...

Marcell Duchamp - "White boat with cockpit drain" - 1917

Effet de Nuit - Night Effect with sailboats Monet Monet Degouve de Nuncques Monet Menton Unknown

If you look closely, you can see two close-hauled sloops sailing neck and neck Impromptu art imitating life, imitating anarchy? As it is painted (fingered?) on glass, hopefully it can be saved and placed in the Musée national de la Marine Paris.

A little pulp cover art from Errol Flynn's first book "Beam Ends". "Beam Ends" is the story of a young Errol Flynn's adventures with his mates, sailing 3000 miles from Sydney to New Guinea in a tired and leaky 50 year-old cutter-rigged 44' schooner "Sirocco".   Though the book claims the...

And what lovely gams...

This is a little different, but there is a sailboat pictured at the start and at the end.

Dennis Orme Shaw, GALWAY HOOKERS, 1960s The largest hookers, Bád Mór, were 35- 40 feet, open and used to carry turf (for fuel) and maybe the occasional keg of poitín (the local hootch) across Galway Bay from Connemara and County Mayo to the Aran Islands and the Burren.  Hulls preserved with...

I know that view.  That's the field where my sailboat came from.  It was just off to the right, out of the frame.  Covered in faded blue tarps...

We've touched on Cubism, but Deconstructionist marine art also deserves a mention...

Checking his phone?

Jean Metzinger  (1883–1956), French,  Scene du  Port (sailboats)   

Another "handcrafted artifice of great utility": . complete with required sailing art: Also suitable for dewatering your bow sprint, and works well with lumpy oatmeal.

Don't forget the great pulp magazine covers