Most of Armstrong’s leisure time was spent on the water as he was an excellent yachtsman. He built a fleet of sailing craft in Bayside. The mothership of his fleet was Amorette, a 40 foot Sonder boat he used to entertain guests. Other craft included Madame X, a centerboard open sloop, Little Income, a Chesapeake Bay sneakbox, he purchased for Louise, two Curry racers Rhythm I and Rhythm II, two decked canoes Oskee Wow Wow and Apache, and his pride an 18 foot decked canoe named Mannikin. Mannikin was designed by Armstrong and built by Bayside carpenter Carl Swenson, who in all likelihood, crafted Armstrong’s famous palette of 3000 pastels. Armstrong’s excursions were not limited to pleasure cruising on Little Neck Bay. He sailed competatively winning many awards. In 1934 and 1935 Armstrong won the American Canoe Sailing Championship, competing against the famed English naval architect Uffa Fox. Fox wrote of his race against Armstrong in his extensive memoirs, The Crest of the Wave. After returning from racing off of the coast of Canada near Sugar Island Fox wrote, “We crossed to Long Island by the steam ferry, finally arriving at Rolf’s home at 3:30 a.m. after 23 hours of driving all in New York State...At the end of our journey we were met by dear old W.P. [Stevens]...We had arrived at the scene of the International Canoe Contest (Bayside) without a scratch on any of the three canoes, weary but triumphant.” The demands of piloting these canoes were such that Armstrong prided himself in staying in top physical condition throughout his entire life. He exercised regularly, was naturally athletic, tall (6 feet), muscular and frequently regaled reporters with tales of his fights as a lightweight boxer during his years as a student in Chicago. Armstrong even prefered shopping at health food stores for wheat germ and sea salt before “health foods” became popular in America. The only part of his appearance he struggled with was his hairline, and chose to wear a sailing hat or a hairpiece later in his life. Model, Jewel Flowers, was purportely the first to approve of Armstrong’s new hairpiece. Since she handled the majority of his personal affairs and posed for him for two decades following their meeting in 1940, he held her opinion in the highest regard. Armstrong called her “Missy” and she always called him “Skipper.”

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