Bob, yes, there was a lot of interaction between Massachusetts and Hawaii, mainly due to whaling. Michener’s book Hawaii mentions New Bedford more than a dozen times, although, of course, that’s mostly a fictional work — a historical novel.

I’ve heard of the Paniolo cowboys but don’t know much about them.

Portuguese were recruited to come as sugar cane cutters starting around 1878. Initially they were from Madeira but later mostly from Sao Miguel in the Azores, mainly because almost 60% of Azoreans are on that largest island. Maybe some were from Terceira. Both the Azores and Madeira grew sugar cane.

New England Christian missionaries had a big influence. Some Portuguese whalemen hopped ship in Hawaii and settled there. Some Hawaiians were picked up as replacements and later settled in New England. In fact, before New Bedford replaced Nantucket as the whaling capital, enough Hawaiians had settled in Nantucket that they started a “heathen school” for them.

I recall a story about a New England church disassembled in New England and shipped to Hawaii to be re-assembled. I can’t locate that info. Perhaps it was in the movie version of Michener’s book. So that might be fiction.