Recorded history suggests that in May 1787 Wynee (also spelled Winee) was the first Hawaiian to leave the islands on a western ship, the British ship Imperial Eagle. She served as the personal servant of the captain’s wife. They headed to China. (Duncan)
“This lady (Barclay’s wife) was so pleased with the amicable manners of poor Winee, that she felt a desire to take her to Europe; and for that purpose she took her, with the consent of her friends, under her own particular care and protections.” (Meares)
Shortly thereafter, on about August 27, 1787, “Tianna (Kaʻiana (also spelled Tyaana & Tyanna,)) a chief of Atooi (Kauai,) and the brother of the sovereign of that island was alone received to embark with us, amid the envy of his countrymen.” (Meares) He was the first Hawaiian Chief to sail from the islands in a western ship.
“Tyanna is tall; being six feet two inches in height and so exceedingly well made, that a more perfect symmetry and just proportion of shape is rarely to be met with … (he) has a pleasing animated countenance (and) a fine piercing eye”. (Portlock)
His father, ʻAhuʻula, was a younger son of King Keaweikekahialiʻiokamoku of the island of Hawaiʻi, making Kaʻiana a young first cousin of that island’s most powerful aliʻi, including King Kalaniʻōpuʻu, Keōua (father of Kamehameha I) and Keawemauhili of Hilo.
Kaʻiana’s mother was the Chiefess Kaupekamoku, who on her father’s side was descended from the ruling houses of Oʻahu and
Hilo, and on her mother’s side was a member of the Maui royal family, being a half-sister of King Kekaulike.
Kaʻiana was thus a first cousin to Kekaulike’s numerous children who included King Kahekili of Maui, King Kāʻeo of Kauaʻi, Namahana (mother of Kaʻahumanu,) Kekuamanoha (father of Kalanimōku) and Kalanihelemaiʻiluna (grandfather of Bernice Pauahi Bishop.) (Miller)
Kaʻiana had two younger half-brothers, Nāmakehā and Nahiolea, sons of his mother by two chiefs of the Maui royal family. The brothers were closely allied throughout their lives; all three were acclaimed warriors. (Miller)
Captain John Meares took Kaʻiana as a passenger to Canton, China (now called “Guangzhou”) with a cargo of furs from America.
Striding through the streets clad in a malo (loincloth,) ʻahuʻula (feathered cape) and mahiole (feathered helmet) and carrying his spear, Kaʻiana was a gigantic figure who terrified the Chinese. (Miller)
“Tyaana often expressed his dislike for the Chinese, particularly that custom of shutting up and excluding the women from the sight of all strangers.” (Portlock)
In China, according to Captain Nathaniel Portlock, “his very name (was) revered by all ranks and conditions of the people of Canton.” From 1787-1788 Kaʻiana visited China, the Philippines and the Northwest Coast of America.
Wynee and Kaʻiana later met in China; Captain Meares acquired two new ships, the Felice and the Iphigenia, and they set sail in January of 1788 for Northwest America, with Kaʻiana and Wynee aboard.
There, in Kaʻiana’s honor, Captain Douglas gave the name “Tianna’s Bay” to the place where the Iphigenia anchored overnight on August 5, 1788, near Alaska’s Mount Saint Elias. It was probably the first foreign place to be named for a Hawaiian person, but modern maps show that site as Icy Bay.
The return voyage began badly; sickness broke out among the crew and Wynee became ill. “Tianna, in his constant attendance upon Winee, had caught a fever, which, with the humane anxiety he felt on her account, confined him for some time to his bed.” (Meares)
“Winee, a native of Owyhee, one of the Sandwich Islands, who possessed virtues that are seldom to be found in the class of her countrywomen to which she belonged”, died aboard the Iphigenia February 5, 1788.
After time in the Northwest, Kaʻiana returned to the Islands on December 6, 1788 on the Iphigenia, captained by William Douglas. They first landed at Wailuku, Maui, with Kaʻiana greeting old friends, leaving the same day for the Island of Hawaiʻi. They touched at Kawaihae and Kailua, where friends and relatives of Kaʻiana crowded on board to see him.
Anchoring at Kealakekua Bay on December 10th Kamehameha came on board to greet Kaʻiana. “(A)fter crying over Tianna for a considerable time, the King (Kamehameha I) presented Captain Douglas with a most beautiful fan, and two long feathered cloaks.” (Meares)
Within a few days, Kaʻiana had decided to remain on Hawaiʻi, as Kamehameha, recognizing the advantage of having with him a chief familiar with foreign ways, had granted him a large property on the island. (Miller)
This was a time of conquest by Kamehameha and warfare across the islands.
“Among the distinguished Hawaiian chiefs connected with the final conquest and consolidation of the group by Kamehameha the Great, and standing in the gray dawn of the close of the eighteenth century, when the islands were rediscovered by Captain Cook and tradition began to give place to recorded history, was Kaiana-a-Ahaula.”
“After giving to the conqueror his best energies for years, and faithfully assisting in cementing the foundations of his greatness, he turned against him on the very eve of final triumph, and perished in attempting to destroy by a single blow the power he had helped to create.” (Kalākaua)
In the battle of Nuʻuanu (1795,) when the army of Kamehameha conquered Oʻahu, John Young (a close advisor to Kamehameha) is credited with firing the shot that killed Kaʻiana.
“By some the defection of Kaʻiana has been attributed to coldblooded and unprovoked treachery; by others to an assumption by Kaʻiana that by blood Kamehameha was not entitled to the sovereignty of the group, and that his defeat in Oʻahu would dispose of his pretensions in that direction, and possibly open to himself a way to supreme power.” (Kalākaua)
By 1795, having fought his last major battle at Nuʻuanu on O‘ahu with his superior use of modern weapons and western advisors, Kamehameha subdued all other chiefdoms (with the exception of Kaua‘i.)
However, after a short time, another chief entered into a power dispute with Kamehameha, Nāmakehā (the brother of Kaʻiana.) Hostilities erupted between the two that lasted from September 1796 to January 1797. (Brumaghim) The battle took place at Kaipalaoa, Hilo. Kamehameha defeated Nāmakehā.
The undisputed sovereignty of Kamehameha was thus established over the entire Island chain (except Kauaʻi and Niʻihau;) in 1810, negotiations between King Kaumuali‘i and Kamehameha I took place and Kaumualiʻi yielded to Kamehameha making Kamehameha leader of all the Islands.
The image shows Kaʻiana.