My choice would be the yacht Reliance of 1903 designed by the famous Nat Herreshoff. I read the book Temple to the Wind a long time ago and could not put it down. That yacht was, for its day, such an extreme design and engineering feat, without computers and all designed and built in a short time. Herreshoff was the master in those days.The yacht measured over 200ft overall with just 90ft of waterline [the huge overhangs were to take advantage of the rating rule when heeled], it displaced 189 tons and had a sail area of 1,500m2 (16,000ft2)! It was massive and with wooden masts that tipped 200ft above the water, an 84ft long wooden spinnaker pole and cotton sails.