After HMCo. changed hands in 1924 and N.G.H. fully retired he had PLEASURE built to his design for sailing in Florida during extended winter vacations. She’s a shallow centerboarder drawing 2 1/2 feet like his previous daysailer ALERION, but with a longer hull and cabin for cruising—which he often did with his wife, Ann. Strangely, HMCo. built no others and, stranger yet, there have been no replicas constructed.

Captain Nat renewed an acquaintance with Commodore Ralph Middleton Munroe in the fall of 1921, when he and Mrs. Herreshoff, aboard his power cruiser HELIANTHUS III, dropped anchor off the Munroe homestead, ‘The Barnacle,’ in Coconut Grove, Florida. During subsequent winters, the Herreshoffs were invited to live on the Munroe property at the waterfront cottage, ‘Fair Haven.’ The Munroe-Herreshoff friendship was wonderfully natural. Both men were boat designers, members of the same generation, and had a keen interest in sailing.

Like N.G.H.’s previous day boat ALERION (finished in 1913), his 30-foot PLEASURE was an outside-ballasted centerboarder. Built in the fall of 1924 and shipped to Floriday by rail, she was used by N.G.H. in Florida during the two winter seasons that followed 1925-26 and 1926-27.

Commodore Munroe was well known for his sensible and seaworthy shallow-draft cruising boats, and it may well have been his influence that helped shape PLEASURE’S model. N.G.H. claimed that her leaner bow, in contrast to ALERION’s full deck line, made PLEASURE a better seaboat, and one that indeed lived up to her name. In his attempt to secure shallow draft and yet retain the desired weight of ballast, N.G.H. designed PLEASURE’S lead keel to encompass the centerboard trunk bedlogs and stub floor timbers all in a single casting. As a secondary benefit, this construction eliminated the usual wooden keel timber from the middle part of the boat.

PLEASURE was donated to HMM by the Yaro family in 1997.