Hawkins and Drake’s Accidental Voyage to San Juan de Ulúa

The fortress overlooking the Port of Veracruz

Before becoming privateers for Queen Elizabeth, slave traders Hawkins and Drake took a detour to San Juan de Ulúa.

The greed of John Hawkins and Francis Drake, pushing to trade contraband slaves in the West Indies, almost cost them their lives. After three successively difficult trade runs, Hawkins pushed for a fourth that resulted in disabled ships deep in Spanish territory near San Juan de Ulúa.

English Slave Traders in the Caribbean

During the 16th century, the African slave trade was dominated by the Portuguese. While the Caribbean was a popular destination for those slaves, the Portuguese paid heavy taxes to the Spanish for the privilege of offloading their ships in Santo Domingo and other Spanish ports.

The Portuguese monopoly on slave trading led to a shortage of slaves on the growing Caribbean plantations and exorbitant prices. This opened the door for other nations, such as France and England, to engage in contraband slave trading. Between 1562 and 1566, John Hawkins made three successful slave-trading expeditions to the Caribbean. His fourth was the springboard into privateering.

Bad Luck from the Beginning of Hawkins’ Fourth Voyage

Despite Spanish protest, John Hawkins sailed six ships from the English Channel into the Atlantic on October 2, 1567 with the intent to “…lade Negroes in Guinea and sell them in the West Indies in truck of gold, pearls, and emeralds.” In addition to the 700-ton Jesus of Lubeck, the fleet included the William & John, the Swallow, the Judith, the Angel and the 300-ton heavily-armed Minion. The Jesus of Lubeck immediately sprang a leak, requiring a stop for repairs in the Canary Islands before proceeding on to the Guinea coast.

Once the fleet arrived off the West African coast, Hawkins found that the Portuguese were no longer willing to trade with him, forcing him to hunt down and kidnap any Africans he wished to sell. For almost three months, he bartered for smaller ships to move inland, attacking African villages and acquiring a mere 150 Africans. He lost nine men to poisoned arrow shots and was himself wounded before events changed in his favor.

An internal war in Sierra Leone led Hawkins into negotiations with one of the African kings. Hawkins agreed to assist the king in subduing the other African tribe, but in exchange he wanted to keep any prisoners. It was an exchange that netted him 260 more Africans to force into the hold of his ship, making a total of 410.

Hawkins and Drake meet Resistance in the Caribbean

In the 52 days it took to reach the Caribbean, only about 2/3 of the enslaved Africans were still alive. After offloading some of their slaves at Borburata, where they overcame some mild resistance, Hawkins sent Drake with the Angel and Judith to Rio de la Hacha with the rest while he went on to Curacao for supplies. At Rio de la Hacha, Drake was immediately fired upon by the Spanish. Drake’s superior fire power allowed him to subdue the town, destroying the governor’s house and sending the citizenry running for the hills. Given his superior fire power, Drake had no problem bartering successfully for pearls and provisions.

Hawkins and Drake used the same tactics in Santa Marta, leaving only 40 slaves left by the time they reached Cartagena. Cartagena was too well-protected, however, and did not need Hawkins’ cargo. As it was now July and hurricane season was imminent, Hawkins decided to head his fleet back to England.

In the Florida Straits, the fleet encountered bad weather and the William & John became separated from the rest. She eventually made her way back to England. The Jesus of Lubeck was badly damaged and after several attempts to get back on course, Hawkins found himself in the Gulf of Mexico looking for a place to put in for repairs. Hawkins had unintentionally ventured into secure Spanish territory where no English ship had dared venture before.

San Juan de Ulúa – Mexico’s Yucatan Peninsula

A convenient meeting with a Spanish merchant ship in the Bay of Campeche pointed Hawkins to the island of San Juan de Ulúa for repairs. His timeline for repairs was a mere 10-12 days before the heavily armed Spanish flota arrived for its annual stop there. After stepping on so many Spanish toes, disabled and far into Spanish territory, Hawkins and Drake were in an extremely tenuous position at San Juan de Ulúa. They had no choice but to seek repairs on an island controlled by the very nation they had been cheating in their contraband business endeavors.

On September 16, 1568, Hawkins and Drake’s ships approached San Juan de Ulúa single file with the English flag flying.


  1. Carini, Marco & Macallan, Flora. Pirates: A Swashbuckling Journey across the Seven Seas. New York.
  2. Lane, Kris. Pillaging the Empire: Piracy in the Americas. U.S. 1998.
  3. Latimer, Jon. Buccaneers of the Caribbean: How Piracy Forged an Empire. Massachusetts, 2009.
  4. Rogozinski, Jan. A Brief History of the Caribbean: From the Arawak and the Carib to the Present. New York. 1999.
  5. Wood, Peter. The Seafarers: The Spanish Main. Time-Life Books. VA. 1979