In terms of six trans-Atlantic trips, that would be quite exceptional, given the deadliness of European diseases among North American Indians.

I can think of two figures in the 18th century who may be similar but surely not as prolific as Squanto. The first would be the Mohawk chief Hendrick (Theyanoguin). He traveled to England in 1740 where met King George II. He was also active in diplomacy with French Canada, New York, and Pennsylvania. He turned on the French during the War of the Austrian Succession (King George's War) and was specifically targeted to be kidnapped by a French war party. He took part in the Albany Congress of 1754 and died fighting with his British allies at Lake George the following year at the start of the French & Indian War. Hendrick was well-known and celebrated among the British and was mourned when he died.

Another figure was an Oswegatchie Iroquois known as "Charles" to the French who was active at the French mission of La Présentation (Oswegatchie). He was a practicing Catholic and worked with Francois Picquet. At some point before 1754 he had traveled across the Atlantic to France where he was received by the royal court. He spoke fluent French and even dressed in the European manner but yet was still able to cross back into the native world. During the French and Indian War he represented his people in conferences with the Governor General of Canada and even disguised himself as a common hunter while working as a spy at British Oswego in 1760.

For Hendrick, see Eric Hinderaker, The Two Hendricks: Unraveling a Mohawk Mystery (2011)

For Charles, I pieced together tidbits about him over my dissertation work...Bougainville's wartime memoir, Adventures in the Wilderness contained the most information. Pierre Pouchot's Memoir Upon the Late War also touches on him as well.

Tisquantum's life, while amazing, is one of many such strange journeys in the expanding Atlantic world. Sadly, abduction into slavery was a common form of first contact along the Atlantic coast. European fisherman and traders routinely supplemented their cargo by abducting a few unwary captives for sale in the Caribbean, Europe, or North Africa. Captives could be sold for profit, or in the case of many Spanish explorations, an initial foray to a new region involved kidnapping several individuals to train as interpreters. Two such captive translators have vastly different outcomes, and provide some insight into the various ways conquest unfolded.

For the first example, Pizarro kidnapped two boys from the Peruvian coast in 1528. The young men were taken to Spain, learned Spanish, and accompanied the Conquest of Peru in 1531. They acted as translators during the famous showdown in Cajamarca in 1532 that resulted in Atahuallpa’s capture. The translators were rewarded for their service. Pizarro granted at least one of the two men, Martinillo, a share of the Cajamarca spoils. Martinillo changed his name to Don Martín Pizarro, and settled in Lima as the Interpreter General with two encomiendas to his name.

Kidnapped Native American translators could also escape their captives, and return to their homeland armed with new languages and valuable insight into European objectives. Don Luis de Velasco, a Native American abducted from the Virginia tidewater region in 1561 returned in 1571 with Franciscans establishing a mission near the James River. Don Luis escaped, and returned with an armed party that killed the Franciscan fathers. We may never know for sure, but there is sufficient reason to believe Don Luis was Opechancanough, brother of paramount chief Powhatan/Wahunsenacawh. Openchancanough would later advise his brother to violently oppose English settlement at Jamestown. His insight led Powhatan/Wahunsenacawh to expand the Powhatan Paramount Chiefdom to better oppose Spanish encroachment in the years preceding the English arrived in Virginia. By the time the Virginia Company arrived to establish Jamestown in 1607 Powhatan incorporated over thirty tributary nations, and held sway over a land known as Tsenacommacah (densely inhabited land).

On the other side of the coin, shipwrecked or captive Europeans often had amazing experiences within Native American communities. In many cases they became vital translators for both sides when their countrymen returned. In Florida and Central America Spaniards were valued in Native American communities as translators and their ability to provide insight into European aims. As an example, in Florida the de Soto entrada encountered Juan Ortiz, a Spaniard captured while searching for the lost 1528 Narváez entrada. Ortiz learned the Timucua language during his years in Florida and served as a translator while de Soto rampaged through the region. De Soto said of Ortiz, “This interpreter puts new life into us, for without him I know not what would become of us.” Interestingly, Ortiz refused wear Spanish dress while traveling with de Soto, and preferred the company of his Mocoso friends, possibly indicating his desire to keep them informed of Spanish intentions. Likewise, the Conquest of Mexico famously required two translators. A shipwrecked Spaniard who lived for eight years among the Maya, Gerónimo de Aguilar, translated Spanish to Maya, and Dona Marina/La Malinche, a Nahua noblewoman from the frontier of Nahuatl-speaking central Mexico, then translated Maya to Nahuatl.

The greatest journey of a shipwrecked Spaniard must be Álvar Núñez Cabeza de Vaca. One of the few survivors of the unfortunate Narváez entrada, Cabeza de Vaca traveled among the Native American nations of the U.S. Southeast, Texas, and Northern Mexico for eight years before re-uniting with his countrymen in Northern Mexico. A map of his journey provides some perspective of the vast distances he covered. Check out his narrative for more insight into his travels.

As these brief examples show, the early years of contact are filled with amazing stories and individuals with unbelievable journeys. If something specific strikes your interest let me, or one of the other flaired users, know. We can make some recommendations for further reading.