Hm, big sailboat, metal, and with that bow not a Nat Herreshoff designed boat.
Which leaves as possible choices:
#1050s Katoura
#1058s Prestige
#1074s Sheerness
#1131s Istalena
#1146s Enterprise
#1147s Weetamoe
#1233s Rainbow
Only Katoura and Sheerness had portholes.
Only Katoura had that distinctive step in her bow profile.
It's Katoura.
Here's some more info on Katoura:
"KATOURA
1927
Robert E. Tod a member of the NYYC, ordered a big yacht in steel, Katoura, from W. Starling Burgess in late 1926. A sloop of this size had not been built since 1914, when Resolute, Vanitie, Defiance, and Shamrock IV first appeared on the scene. Katoura was designed under the Universal Rule, and her waterline length of 75 feet earned her a rating of 68-1/2 foot. Katoura was thus the first yacht to be classed as a J (rating between 65- and 76-Foot). However, her low rating would have prohibited her from racing for the Cup against 76-foot J boats. Her size aside, the second particularity of this sloop lay in the building method, which complied with Lloyd's scantling rules for yachts longer than the 12-Metre boats of the International Rule. This intentional decision was significant, as Tod intended to go to Great Britain for the 1928 racing season.
Nor was it by accident that he chose to limit the waterline to 75 feet; this option would enable him to pit himself against the British big-class yachts.
The launch of Katoura did not go unnoticed. To begin with, the rumour of her Atlantic crossing to Europe, planned for 1928, incited some eminent British yachtsmen to place orders for new 23-Metre boats, for the first time since 1908! In addition, the new International Measurement Rule adopted in 1928 classed Katoura, which had been born a Universal Rule yacht, as a 21-1/2 Metre. This was the first step toward the gradual merger of the Universal and International Rules.
The most surprising aspect of the story was that Katoura, having shaken the yachting world, never came to Europe. Built at the Herreshoff shipyard and launched on 2 May 1927 after being christened by Tod's daughter Katherine, the yacht's first racing season produced mixed results. Sold at the end of the season to Frank L. Crocker from New York, who renamed her Blackshear in 1928, the boat, which now had an auxiliary engine, came into the hands of William Forbes Ingold in 1932 and was renamed Artemis. In 1934, the sloop was bought by E. W. Clucas and had her name changed again, this time to Manxman. Clucas converted her into a yawl in 1936. At the end of 1947, he sold her to John N. Mathews. In 1954 the yacht, which had become the property of the Madrilene Dr. Alfonso Bueno, was called Roraima and was based at La Guaira in Venezuela. In 1957 Roraima belonged to the Venezuelan Naval School. All trace of her was lost in 1958." (Source: Chevalier, Francois and Jacques Taglang. J Class. London, 2002, p. 141-142.)
