The fleet had set sail, gliding across the calm waters of the Mediterranean.
Over the next few weeks, Isaac's fleet traveled intermittently along the western Mediterranean coast, passing by the shores of the Kingdom of France and the Crown of Aragon, steadily advancing toward the edge of the known sea.
When they neared the southern coast of Granada, pirates began to appear more frequently. The emirates along North Africa's coastline and the southern reaches of Iberia, including Granada, often targeted merchant ships in these waters.
Fortunately, the shipbuilding techniques of these infidels were still rudimentary—they lacked the capability to construct large warships.
Isaac fended off several small pirate vessels that came to harass them, without much delay.
On June 20, 1445, according to the Gregorian calendar, Isaac led the fleet through the Strait of Gibraltar, entering the Atlantic Ocean.
The moment they entered, the fleet—accustomed to the relatively gentle sailing conditions of the Mediterranean—began to struggle.
The Atlantic's choppy swells and unpredictable weather left even the seasoned Genoese crossbowmen and French knights seasick once again.
The fleet had to hug the coastline and proceed cautiously while adjusting to the new conditions.
By June 28, 1445, Isaac finally arrived at the destination of his voyage—the westernmost point of continental Europe:
Lisbon.
This city, the capital of the Kingdom of Portugal and the Algarve, sat on the eastern shore of the Atlantic Ocean. The Tagus River flowed to the south of the city, and the Sintra Mountains stood like a shield to the north.
Isaac anchored the fleet nearby and went ashore with William, Fidel, and Conti, instructing the rest of the knights to intensify their training of the refugee recruits.
At this time, Lisbon was still a medium-sized city—far from the scale of Genoa or Rome—but it radiated a spirit of ambition and vitality from every corner.
Over the past decade or so, successive Portuguese kings had waged campaigns in Morocco, successfully seizing Ceuta, fortifying it, and withstanding counterattacks from the infidels.
The influx of North African slaves, livestock, and gold greatly enriched Portugal's treasury and stabilized the lives of its people.
The previous kings—John I and Duarte I—were both capable monarchs. They reined in the land-owning nobility, developed the navy, and established a provincial governor system.
Though these governors were often appointed from the nobility, it was a significant institutional leap.
They had also solidified a national strategy tailored to Portugal:
Ally with England to resist Castile in the north.
Expand southward into North Africa to control trade routes.
Simultaneously, they encouraged oceanic exploration, promoted ship innovation, and officially sponsored expeditions along the West African coast.
By this time, Portuguese shipbuilders had grasped a basic understanding of Bernoulli's principle, realizing that altering sail design allowed for sailing against the wind.
Portugal had, over decades of exploration, discovered the Madeira and Azores archipelagos and gradually extended its reach down the African coastline.
In 1434, a fleet sponsored by Prince Henry the Navigator successfully rounded Cape Bojador, reaching the fabled "Green Land."
By 1440, Portugal launched its first caravel—a ship that combined storm resistance with long-range capability. For centuries to come, caravels would dominate the oceans and lead the discovery of entire continents.
In 1444, Prince Henry captured hundreds of Africans and sold them in Italy. For the first time, his ventures saw meaningful returns.
Prince Henry the Navigator—the legendary explorer—was the final name on Isaac's list.
At this point in time, Prince Henry had yet to fully tap into West Africa's vast population and gold resources. His expeditions were still running at a loss, drawing criticism from many domestic nobles and merchants.
It wasn't until 1448, when Henry defied opposition and established the first fortress on Arguin Island, near Cape Blanco, that the true exploitation of West Africa began.
The wealth of slaves and gold transformed Portugal from a peripheral nation into a rising maritime powerhouse.
Prince Henry's reputation shifted from scorn to praise.
Isaac had come precisely to capitalize on this window of opportunity—before Portugal monopolized the spoils.
West Africa was vast, filled with countless tribal peoples—enough to be divided and exploited for generations.
In truth, even by the time of the Berlin Conference centuries later, many parts of Africa had yet to be touched by colonizers.
The immense gold reserves there would greatly ease Isaac's financial strain, allowing him to build a massive fleet and hire a formidable army.
Plundering West Africa was the most critical part of Isaac's plan to revive the Roman Empire.
Thanks to the widespread use of the compass and advancements in astronomy, the technical barriers to exploring West Africa were already overcome.
A fleet composed of caravels and carracks could easily carry sufficient supplies.
What held back exploration was the lack of visible profit.
Henry and his backers might hesitate or be disheartened after encountering the ignorance of African tribes.
But no one understood the potential of these lands better than Isaac.
When Henry died, the gold discovered in his estate stunned all of Lisbon.
Isaac entered Lisbon, found an inn, and tasked William with delivering a letter to Prince-Regent Pedro.
After King Duarte's early death, his son Afonso V inherited the throne, and his brother Pedro acted as regent.
He now controlled the government.
As Isaac strolled through the streets of Lisbon, he observed a thriving city and bustling crowds.
"Did you hear? Prince Henry is being questioned again by the Merchants' Council."
"Ridiculous! If these oceanic ventures succeed, the returns will be unimaginable."
"So far, they've only brought back a few hundred blacks. My cousin bought a few—they're useless, just wasting food…"
"Hah! Your cousin's as dumb as a wild boar. And he expects to find clever slaves?"
"Why you—!"
…
Along the way, all Isaac saw was hope and stability.
Nothing like the anxiety and uncertainty that plagued Constantinople and Athens.
This country, forged in the crucible of the Reconquista and guided by generations of wise kings, had finally found the right path.
Nobles were restrained. The citizen and merchant classes were rising. Maritime exploration was expanding.
Newly discovered islands eased population pressure and expanded influence.
Confidence in sailing was growing. Technological innovation was continuous.
While the rest of Christian Europe remained in decline, Portugal stood out.
The next day, Isaac was granted an audience with Prince Pedro.
He stepped forward and paid proper homage.
"Greetings, Your Highness, Prince-Regent," Isaac said in Latin.
"No need for formalities, young one," Pedro replied in fluent Greek.
Isaac was startled.
"Don't be surprised," Pedro smiled. "When I was a prince, I loved to travel—visited every major European city. I met your father and the Sultan of the Ottomans."
"My father often spoke of you—a nobleman of great learning and virtue," Isaac improvised.
"When I met him, he was eight and still had a runny nose," Pedro said dryly.
Isaac blushed. William snorted with laughter.
"Now, tell me. Why have you come so far?" Pedro asked.
"Your Highness, I am deeply interested in Prince Henry's expeditions and wish to join them—with your permission."
"Oh? And how do you plan to join?"
"I have a fleet. A printing press in Rome. A trade company with steady monthly income."
"I hope to contribute ships and funding to Prince Henry's enterprise."
Isaac presented the papal decree and Genoese documents.
Pedro examined them and paused.
"Child, you've already achieved something remarkable. Why risk it all on a vague dream?"
"Henry is currently seeking support. If you insist on joining, I won't stop you—but prepare to lose everything."
He stepped forward and patted Isaac's shoulder.
"Others have gone before you—some never returned. Some returned mad. Some came back empty-handed."
"Regardless, I wish you luck."
Pedro signed a permit bearing the seals of both the Pope and the Portuguese crown, granting Isaac's fleet the right to resupply at Portuguese ports and to retain all gains from exploration.
Isaac accepted it as though it were a treasure.
"Thank you for your generosity!"
Pedro waved him off.
That night, Isaac summoned his commanders and officials to organize the coming tasks.
He would take the Moria Grand Duke and St. Nicholas as exploration vessels to join Prince Henry's fleet.
The remaining ships would stay at Ceuta, under William's command. They could occasionally sail out and raid infidel supply ships.
Conti and the knights would settle at Ceuta with the southern French refugees, training diligently while awaiting Isaac's return.
The Genoese crossbowmen, offered a new round of pay, agreed to sail with Isaac—under the command of Maruna.
The next day, Isaac set sail with his two ships toward Cape St. Vincent, the headquarters of Henry's exploration campaigns.
With the northwest wind, they hoisted sails and reached Cape St. Vincent by nightfall.
Once barren, the area had become a bustling trading town since Henry made it his base.
A devout man, Henry had established churches and monasteries nearby.
The nearby town of Sagres housed a famous nautical school and a naval arsenal.
Henry recruited talent regardless of origin—Moors from North Africa, Arabs from the Middle East, and Norman pirates from the North.
As long as they had maritime skill, they were welcome.
Security was tight. With an escort boat, Isaac entered the harbor.
He was led to Prince Henry's receiving chamber.
The room was sparsely decorated. The most striking feature was a map of northwest Africa.
To Isaac's eyes, it was riddled with errors—crude and imprecise.
But in that era, every sea route had to be carved out through blood and storms. The effort required was unimaginable.
Isaac stared at the map in silence.
"A beautiful place, isn't it?"
Prince Henry entered from a side door, smiling.
"Indeed," Isaac replied.
"I hear you want to gamble with me?" Henry poured them each a drink.
Isaac took a sip—burning and sharp.
"Cough, cough!" He couldn't help but choke.
Henry laughed heartily.
"That's cane liquor—sailors love it more than their wives."
He downed his own glass in one gulp.
"Your Highness, I truly am interested in your expeditions."
"I saw your ship—a fine carrack. Ready to sail."
"The galley will need modifications. We'll fit both lateen sails and square sails."
Henry refilled Isaac's cup.
Isaac hesitated—then drank it all.
"That's more like it!" Henry beamed.
He handed Isaac a contract.
"Others have dared to join me. These were the terms. Look it over."
"Discuss any changes with my advisors. We'll start refitting your ships here."
"How much will it cost?" Isaac asked.
"For you? Free—since you drank with this old man!" Henry waved it off.
Over the next few days, Isaac and Henry's advisors debated the terms intensely.
In the end, Isaac agreed to pay 5,000 ducats as compensation for using Portuguese ports.
He emptied his wallet and promised to pay soon.
He provided one carrack and one refitted galley—the St. Nicholas—to join Henry's fleet.
Henry contributed four caravels and several supply ships.
Isaac would join in person; Henry appointed Captain Fernando as his representative.
Their mission: to locate the mouth of a great river described by natives and to scout potential colonial islands.
On July 10, Isaac finally received profits from his Roman printing press and the first dividend from the Montferrat Trading Company.
The trade fleet had returned successfully. Isaac breathed a sigh of relief.
He slammed the 5,000 ducats onto the accountant's table and stepped outside.
Looking at the ready ships, his heart fluttered with excitement.
The next day, the fleet raised anchor.
As he watched the land fade behind him, Isaac felt a deep surge of emotion.
There was no Belém Tower, no Age of Discovery Monument, yet he couldn't help but whisper the words that would echo through history:
"Here ends the land. From here begins the sea."