A Jewish man makes a fortune and buys himself a large yacht. He outfits himself in a braided naval jacket and a nautical cap. Then he invites his mother onboard.
“This is my yacht, and I’m the captain,” he tells her.
Says his mother, “By you, you’re a captain, by me, you’re a captain. But by the captains, you’re not a captain.”
— Classic Jewish joke
A Monsey resident — by way of Germany and Spain — says he will emulate the footsteps of Jewish travelers from the 17th-19th centuries this spring, aboard a 77-foot-long schooner on the Hudson River.

The Red Sea, with the New York skyline in the background.
Nesanel Reed, an avid sailor for most of his 56 years, is the founder of Metrosails, a business that will begin offering kosher day tours and private cruises on the river and in New York Harbor in late April or early May.
His ship is the Red Sea, a schooner he bought in Kenosha, Wisc., refurbished extensively and steered last year, with its sails-and-motor-power, through the Great Lakes, Erie Canal other water routes to its eventual home in Brooklyn Bridge Park’s Pier 6, “which is reserved for historical vessels.”
Reed, a native of Pittsburgh, calls Metrosails an unaffiliated enterprise, New York’s only recreational cruise firm based on a “traditional” schooner (a sailing ship with two or more masts, which dominated the seas for several decades), and the only one under Orthodox Jewish auspices.
The Red Sea, a replica of an 1830s working schooner, is named for its color, not for the body of water through which the Israelite slaves escaped from ancient Egypt, Reed says. “The hull of this vessel is fire-engine red. The boat used to be named Red Witch. That wasn’t going to do for us,” he says.
“Us” includes Yitzy Geisinsky, Reed’s business partner whom he met at the Crown Heights Young Entrepreneurs Initiative.
They are aiming their onboard activities — which will include lectures on Jewish and maritime themes, mincha services during afternoon sails, and possibly Sunday morning “learning and davening, followed by a brunch cruise” — especially schools and camps and other organizations, as an alternative to standard, land-based leisure time offerings.
Reed says he is open to hosting Sheva Bracha meals, engagement parties and Bar Mitzvah celebrations.
He is, figuratively, on firm ground in starting a business that is anchored in the water, calling a ship familiar historical territory for Jews.
In April, 1654, a group of 23 Sephardic Jews in Recife (a major Brazilian port city), the New World’s first organized Jewish community, boarded a ship to escape pending persecution and expulsion. The country, recently reconquered from the Dutch by Portugal, threatened to reinstitute the Inquisition of non-Christians.
The 23, who landed in September in New Amsterdam (later, New York City), after reportedly being taken hostage by Spanish pirates near Cuba for a short time, became the nucleus of the first recognized Jewish community to settle in the country that would become the United States.
Their final ship, the St. Catrina, French, was sail-powered. It is sometimes identified as a schooner, but that design of ship did not come into wide use for about a century.
In 1733, according to the New Georgia Encyclopedia, the first Jews to arrive in that Southern state “were a group of 42 men and women who came on the schooner William and Sarah.”
Two centuries later, during the time of the Holocaust, schooners and other types of boats were among the vessels manned by sympathetic Danes, which helped spirit endangered Jews from Nazi-occupied Denmark to safety in Sweden.
In other words, if you were thinking of taking part in a lengthy voyage for much of pre-20th-century Jewish history, or any history, you probably thought of a ship, a schooner or one of its predecessors.
Sailing ships of all sorts played a major role in Jewish history over the last several centuries — in large numbers, for immigration and commerce; in much smaller, often-exaggerated numbers, for pirating and slave-trading.
“Jews have wandered the earth for thousands of years,” Reed says. “A lot of it [consisted of] traveling on ships. That’s how everybody got to the New World. Sailing [i.e., finding new, safer homes] was part of the lives of Jews for a long time.”
Some of that was local. “Jews have literally been sailing the Hudson for at least 300 years. We’re in good company.”
Paul Foer, a veteran sailboat tour provider and Jewish maritime historian from Annapolis says he agrees with Reed about the presence of Jews on the waters around New York City, “but [it was] mainly for commerce, because recreational sailing is fairly new on the maritime scene . . . the relationship between the vast number of Jews who arrived, then settled, in and around New York, which is of course a major port city, has always put huge numbers of immigrants in close contact with the sea and rivers surrounding New York.”
Foer praises Reed for introducing the current Jewish community to the world of ships and sailing, However, he cautions against conflating the eras of Jewish immigration with the type of vessel that Reed has restored.
It is “highly unlikely” that a schooner like the Red Sea, a coastal schooner, was the type that brought many Jews to North or South America or the Caribbean during most of the previous centuries, Foer says. Schooners originated in the 17th century in the Netherlands, but came into prominence in the late 18th and early 19th centuries, then were eclipsed by steam-powered ships as the age of sail declined.
Foer points out that “the vast number” of Jewish immigrants who came to the US “did come to New York, and they came by ship, of course, but mainly on steam ships at the end of the 19th and early 20th centuries.
Travel between the major American and Caribbean sea ports where most of the early Jewish settlers lived may have been more likely to have been aboard a schooner, rather than a square-rigged ship.
Foer says he shares Reed’s enthusiasm for sharing the history of Jews on the seas with contemporary Jews. “My interest is bringing this story to light.”
Reed’s strong point is the location, Foer says. “New York is above all a world-class port city.”
Reed says university-level scholarship has belatedly recognized the contributions of Jews to maritime history. “Since the 1990s, a new academic area of study has arisen about ‘Port Jews’ — such as those who were involved in seafaring and maritime commerce in the port cities of Europe during the Middle Ages,” he says.
He says the idea for Metrosails was born in the home of the New York Giants.
Reed, who had begun sailing with his family in Pittsburgh, says he was intrigued by the pictures of schooner ships that accompanied the advertising for the 13th Siyum HaShas (celebration of the completion of the seven-year cycle of daily Talmud study), illustrating voyages on the sea of Talmud. The festivities were held in early 2020 in MetLife Stadium, where the NFL Giants play.
That sparked his interest in what grew into Metrosails. “I always had a passion for large schooners.”
Multi-lingual Reed, who had been thinking of starting a new business to replace the translation service, was back in the US, after more than a decade and a half in Europe. His translation business was losing ground to computerized translation programs, so he would pivot to his longtime maritime interest. He would give contemporary Jews a taste of the type of transportation in which their ancestors had participated, the type of vessel in which they had travelled.
With Merchant Mariner certification as a “master” (i.e., a captain) Reed is a captain to the captains, entitled to wear epaulets on his shirt and as well as a captain’s hat.
Though his rank and vocation-avocation are a relative rarity in Jewish circles, he made several unexpected Jewish connections during his purchase of the Red Sea and its voyage to New York City. beginning with the owner of the 41-ton, double-masted gaff-rigged ship with 55-high sails. He was Jewish.
The vessel will not stray far from New York City.
And he will not stray far from his interest in Yiddishkeit.
As a captain, “I think I will be able to make contact with less-frum Jews on the boat in a way I otherwise would not,” Reed says. “I saw in Kenosha that because I was working on the boat, Jews felt comfortable to approach and speak with me, even though they may not have left so comfortable to do it in another setting.”
Will the boat have a mezuzzah?
“It’s not a simple halacha,” Reed says, “because some people — the crew — do sleep on the boat. In the final analysis, a boat does not need a mezuzzah. However, we have one on board because several rabbis have said we should have one for protection.”
The Red Sea can accommodate 49 passengers.
The ship will operate during rain, or other rough weather — as long as it is safe, Reed says. “This is an outdoors experience.”