Let’s understand what a two-meter wave means. When your ship goes from the crest of a wave to the bottom of it, you see the height of the sea above your head. And then you can understand what it really means to make a bircas hagomel. Some poskim say that air travel today doesn’t require bircas hagomel since it is so safe. Driving a car is statistically more dangerous. On a boat, though, you understand viscerally that despite the best equipment and piloting skills, you also need Divine providence. I’m not the nervous type, but I did feel a little anxiety at one point, when I realized there was nothing between us and the ocean depths except for the thin fiberglass keel of the boat.

And then you have to consider pirates. The thought might conjure up images of Captain Kidd or Long John Silver, peg legs and eye patches, but the reality is that pirating is big business these days. Modern pirates are equipped with satellite phones, GPS and sonar systems, modern speedboats, mounted machine guns, and even grenade and missile launchers. Certain seas — most notably the waters between the Red Sea and Indian Ocean, off the Somali coast, and in the Strait of Malacca and Singapore, which are used by over 50,000 commercial ocean liners and tankers a year — are rife with modern privateers who hijack ships for ransom, looting, or political ends. Since 2008, Somali pirates centered in the Gulf of Aden have made about $120 million annually, although with heightened security, their heyday seems to be over.

But as an Orthodox Jew sailing along the vast, seemingly endless Atlantic Ocean, my imagination took me back to the days of… quite surprisingly, Jewish pirates.

Revenge of the Jewish Pirates

This largely unexplored area of Jewish history reads like a swashbuckling tale of adventure. With the expulsion of the Jews from Spain in 1492, on the very day Christopher Columbus set sail in search of a passage to India, many crypto-Jews found their way to the New World in order to escape the long arm of the Inquisition. There is documented proof of at least one crypto-Jew on Columbus’s boats, and some historians speculate that not only were there many more, but that Columbus, too, was a Jew.

In this early age of exploration, up-to-date maps were the currency of success and were held close as state secrets. The great maps of this period of exploration were drawn by Jewish scholars, geographers, and mathematicians in Portugal who essentially controlled the science of navigation. The Ralbag, a French Rishon, was also a mathematician who invented “Jacob’s Staff,” one of the epoch’s most important navigating tools, which uses the angle of the North Star to the horizon to calculate a ship’s location in latitude. Vasco da Gama, the great explorer and the first to round the southern tip of Africa going to the East, credits his “Hebrew tutor” for teaching him mathematics, astronomy, and navigation.

While the Jewish contribution to navigation is well documented, until recently, history books rarely noted the exploits of Jewish pirates, despite their surprising prevalence and success. But historic graveyards unearthed in the Caribbean Islands within the last two decades have revealed tombstones with Stars of David, Hebrew inscriptions, and the pirate’s skull and crossbones insignia.

Some Anusim — the crypto-Jewish forced converts who lived under the threat of death from the Spanish Inquisition – managed to leave the Iberian Peninsula and found their way to Amsterdam and England, both of which were enemies of Spain. And so began a period of Jewish buccaneers exacting their revenge on the Spanish and Portuguese by seizing their gold ships for themselves or the other crowns. One of these men was Rav Shmuel Palacci, scion of a great family of rabbis for generations, who grew up in the Jewish quarter of Fez, Morocco. He left his home in order to support a Jewish community of Anusim in Amsterdam, which would become one of the most important commercial centers of the period and a stop on the escape route of Jews fleeing the Inquisition. Rav Palacci was also a diplomat for the Turkish sultan who was then fighting Spain, and he commanded a small Moroccan fleet that seized Spanish vessels for the king of Morocco, with whom he pushed forth a treaty with the Netherlands. As a pious rabbi, he made sure that his crew kept kosher on the ships, and donated a tenth of their loot to charity.

When Christopher Columbus discovered the New World, he was granted the island of Jamaica in perpetuity as a reward for his discoveries. He wrangled it out of the king of Spain, and was adamant that the Inquisition not be allowed on the island. Clearly, he understood the advantages of freedom for Jews and the economic implications. Many Jews eventually made their way to the new colonies, where they became sugar farmers, merchants, and even politicians, filling Jamaica’s legislature.

By the early 1700s some of these descendants of Spanish-Portuguese Jews sought a more adventurous life on the ocean, and, running ships with names like Queen Esther, Shmuel Hanavi, and Magen Avraham, Jewish sailors began roaming the island coasts in search of riches. These Jewish pirates most frequently attacked Spanish and Portuguese ships, payback for generations of oppression.

Moshe Cohen Hanarkis was one of the most famous of these revenge-seekers. In 1628, he helped the Dutch West India Company’s Admiral Piet Hein pull one of the most lucrative sea heists in pirating history, stealing enormous amounts of gold and silver — worth today over $1 billion — from a Spanish fleet off the coast of Cuba.

Hanarkis wasn’t the only one. One Turkish-born captain, known only as Sinan and called “the Great Jew“ by his Spanish targets, worked alongside the dreaded pirate Barbarossa, had a Star of David on his ship’s flag, and was so proficient at maritime navigation that others claimed he used Jewish mysticism — or perhaps black magic — to find his way. He was buried in a Jewish cemetery in Albania.

Another notable Jewish pirate was Yaakov Koriel. When Koriel was a child, his parents converted to Christianity under pressure from the Inquisition, yet as a captain of a Spanish fleet, he was caught by the Inquisition but eventually freed by his own sailors, most of whom were themselves crypto-Jews. For many years after that, his only goal was revenge, and he commanded three pirate ships in the Caribbean that targeted Spanish vessels. It is said that in his old age he did teshuvah, made his way to Eretz Yisrael where he studied Kabbalah with the Arizal, and is buried in the city’s old cemetery.

Perhaps the most influential of all Jewish pirates was Jean Lafitte, the historical figure known for his key role in Andrew Jackson’s success at the Battle of New Orleans during the War of 1812. After that success, the president presented him with US citizenship. In his personal Chumash which he kept close at hand on his ship, is an inscription which reads: “I owe all my ingenuity to the great intuition of my grandmother, a Spanish Jewess, who was a witness at the time of Inquisition.”

A pirate named David Abrabanel, evidently from the same family as the famous Spanish rabbinic dynasty that included Don Isaac Abrabanel, joined British privateers after his family was butchered off the South American coast. He used the nom de guerre “Captain Davis” and commanded his own pirate vessel named the Jerusalem. According to at least one report, he was the person who discovered what is now called Easter Island, a volcanic Chilean island in the southeastern Pacific Ocean.

I thought of our ancestors plying their courageous pirating profession in these selfsame waters. Every island’s “treasure cove” or “dead man’s point” made me wonder which Jew had been there hundreds of years earlier cloaked in a Christian mantle while searching for religious freedom. I can only imagine the jubilation and sense of justice of a Marrano captain who captured a galleon of much-needed Spanish gold or silver on its way back to the empty coffers of the monarch.

Out to Meet Shabbos

My mind was brought back to the here-and-now, when on Friday morning we had a problem with the gas. We only got it back up working in the afternoon, and I went into high gear cooking in the tiny furnace of a galley. I made dough for challah and it rose quickly in the heat. I put up the chicken soup and got it boiling. All this while being tossed around by the waves. To help combat the constant movement, the stove has two unique features: First, there’s a metal bracket screwed onto the oven to hold the pot in place. Second, the entire stove is on a hinge allowing it to stay straight while the boat rocks back and forth. We had hoped to catch a tuna before Shabbos, but had no luck there. (That was too bad. I had even brought along sushi accoutrements should we succeed.)

As the sun began to set, I put on proper pants and a white shirt, not your typical sailing attire. I then went up to the bowsprit, the narrow extension that protrudes off the front of the boat by three or four feet and sticks out over the ocean. I sat on the very tip of it with my feet dangling above the waves while moving up and down with the boat, like an amusement park ride. I looked around for 360 degrees and saw nothing but the majesty and grandeur of Hashem’s world. Sky and sea were the only things visible, and I felt so small I finally understood what the phrase “a drop in the ocean” really means. Sunset came in a cacophony of color and only with an uninterrupted view to the horizon can one really understand Chazal’s halachic descriptions of the sky during twilight — bein hashmashos. With flying fish literally jumping out of the ocean in front of me, I davened Kabbalas Shabbos, alone with my thoughts and the world.

The rest of the crew, while not religious, was understanding and respectful of all of my needs. They were actually quite enthusiastic about having a Shabbos meal with Kiddush and hamotzi. Sitting in the stern of the boat, huddled around a little table, we sang Shalom Aleichem and got ready for Kiddush. Matan, the young captain of the boat and my patient back in Jerusalem, was really was excited. I offered him the siddur and after we poured the wine that I had brought from Israel, Matan made the Kiddush. I then washed and we made hamotzi. Food always tastes special on the water, and if there was a most delicious challah in the world that Shabbos, it was the one we ate that night swaying with the waves of the sea.

The particular concerns of chillul Shabbos on a boat, while very real, are not necessarily a definitive thing these days. The ropes, so ubiquitous on ships whose sails were once tied with knots — an issur on Shabbos — are now wrapped around cleats in a figure-eight motion. The rudder itself is mechanical and has no electrical component. With a modern autopilot making slight adjustments to the helm using a constant GPS signal, steering the boat doesn’t really need to happen. So you are sitting sound in the back of the boat at night, barreling ahead and not really looking at where you’re going. Occasionally we’d see a big container boat or a fishing vessel on the horizon, but nothing more. It would take an hour or more to reach anything in the distance in any case. A GPS, an autopilot, and an open sail can take you to eternity.

On the ocean, when the sun sets on a moonless night, there is a darkness so intense that it is almost palpable. But the real miracle becomes clear when you look up into the sky and you see things that you never knew existed. The pasuk says that the Jewish People will be like the “stars of the sky.” The endlessness of the sky, the truly countless stars, and the Milky Way jump out at you like never before. During the journey, I’d take to lying out on the deck nightly just to watch the heavens and see the shooting stars.

Shabbos passed with davening, food, sleep, and learning. As the day ebbed, we could really understand what it means to see three medium-sized stars, for they are so clear when they come out. With no light pollution you can begin to see larger stars well before Shabbos ends, hence Chazal’s injunction of sighting medium-sized stars. Once we made Havdalah, my first-ever Shabbos on a boat was complete.

Stuck in the Water

We had been heading south toward Panama at seven knots, not a bad clip, when we were totally becalmed by the winds. I was unprepared for what that meant. We were stuck, simply sitting on the ocean. There were no waves, just slow swells gently heaving the boat up and down. We live in a world where we think we can control time and nature, but nature and weather are much stronger than we are, making the best-laid plans of men meaningless.

We had planned to sail straight to Panama, but had been told of a tiny Colombian island called Isla de Providencia along the way and decided to stop there. If one can conjure up the image of a tropical island paradise, this is the place. Originally discovered by Columbus, it was settled by the Netherlands. I wonder which Anusim might have found their way there — this spit of land, like a volcanic island with luscious green vegetation, palm trees, and white sand beaches in the middle of nowhere — with the freedom the Dutch afforded them.

Today there are about 5,000 people living on Isla de Providencia, and when I took our dinghy from the anchorage to the shore, I sat on a bench and a local man started to speak to me. He wanted to know what the hat was, indicating my kippah, and I told him I was Jewish and from Israel. He was a high school philosophy teacher of all things, and he waxed poetic on how great Israel was — going from a dry desert to a green powerhouse and a world leader. I felt good that even in the middle of nowhere we still have people who respect us. Delays kept us at sea longer than expected. I needed to get back to Israel, so when I saw a small landing strip, I hopped on a tiny plane to the next island of San Andreas, and from there to Bogota, Colombia, and home via Frankfurt.

I think I got a few extra gray hairs when I was on the return leg. I had arrived at the Isla de Providencia on the boat, fully planning to continue on to Panama. Since we came to the tiny island by boat, my passport was never stamped upon entering Colombia. In theory it was no big deal, as it would have just been stamped upon entering Panama, and nobody would have been the wiser. However, I had decided on the spur of the moment to cut the trip short a few days and flew from the island’s small landing strip to Bogota for my return to Israel.

I arrived at the airport in Bogota —uncharacteristically early, I must say — and when I went to check in, they asked me where my entry stamp was. I realized that since I had come into Colombia without getting my passport stamped, my sailing adventure was looking pretty fishy to emigration. I was having visions of being prosecuted as some sort of drug runner who entered the country in the middle of the night via the jungle. I ran to customs and tried to explain myself. After a tension-filled hour, I managed to get the stamp, and got my luggage on the plane with ten minutes to spare.

Thanks to Our Wives

If someone ever asks you for a joke about halachic sailing, it might go something like this:

As the rabbi began to say the Mi Shebeirachs one Shabbos morning, he was handed a note to be read to the congregation.

The note said, “Chaim Goldberg having gone to sea, his wife requests the prayers of the congregation for his safety.”

The rabbi picked up the slip and read aloud, “Chaim Goldberg, having gone to see his wife, requests the prayers of the congregation for his safety.”

Without wives who understand and accept our own passion for traveling, we could never do it.

I can’t tell you if the reality of the trip matched my dreams. However, encountering the wonders of nature out there alone on the ocean was breathtaking, and for me, it was a spiritual event as well. Our ancestors traveled by sea at great risk, and the halachah reflects that. Battling the elements and praying with all their hearts for a safe arrival, were they, too, able to focus on the ocean’s majesty and feel the intimate connection with the Holy One? I hope so. Because for me, it’s a lesson I’m taking with me for the rest of my life.

(Originally featured in Mishpacha, Issue 619)