Scenario: After capturing the Fuerte San Felipe de Lara on the Rio Dulce and plundering the bodegas on the shore of Lake Izabal in the Gulf or Honduras, then selling the goods at Jamaica, buccaneers associated with John Coxon seek more profit. They purchase a commission for ten pieces-of-eight, and forge it to three years: it is probably no more than an English “let-pass” to cut logwood in Honduras and make reprisals if attacked, or a French permission to fish, fowl, and hunt on Hispaniola and make reprisals if attacked.

On January 7, 1680, a buccaneer flotilla consisting of Captains Coxon, Sharp, Essex, Alleston, and Magott sets sail from Port Morant, Jamaica for a rendezvous at Isla Fuerte. Soon after departure, Capt. Jean Rose joins the expedition. Most arrive at Isla Fuerte, but Capt. Sharp is believed lost at sea, and Capt. Essex is delayed. Coxon commands a small expedition to steal canoes and pirogues for the attack. Essex arrives, then all set sail for Golden Island where the expedition is joined by Capt. Edmund Cook who, dispatched as a messenger, ends up too far to windward. The rest of the buccaneers are embayed at the nearby Isle of Pines, and so from here the attackers set out in canoes and pirogues. By accident they meet with Capt. Lessone, who also joins the expedition.

The Isthmus of Darien Showing the Coast from Port Escribano (Escrivain) to Portobelo.
The Isthmus of Darien Showing the Coast from Port Escribano (Escrivain) to Portobelo.

In February, on a day unrecorded, the buccaneers land on the Isthmus at Puerto Escribano, about twenty leagues east of Portobello, and head out afoot. With luck they will avoid

the Spanish watchtowers. For three nights the buccaneers march over rough rocky terrain, sleeping by day, until they reach their target. By doing this, the attackers avoid all three of Portobello’s forts, and the corps du garde as well. The buccaneers have surprise on their side: Portobello is unprepared for them.

Description: Located on the Isthmus of Darien in the Castilla de Oro (“Golden Castile”), Portobello is home of the great trade Fair in which Spanish goods and money from the South Sea, Portobello is always kept in mind as a potential target. Located on the Caribbean coast of the Isthmus of Darien, it is the embarcadero for all South Sea treasure headed to Spain, except for that exported from Mexico. During the treasure fair, when silver transported from Panama to Portobello via mule trains called recuas, and goods transported via canoe and piragua, are traded and readied for shipment to Spain via the treasure fleet known as the Galeones, the city is crowded, raucous, filled with all classes of society, ethnically diverse—it literally has the atmosphere of a non-stop fair for months. But the rest of the time the town is quiet and fairly poor, its rich merchants having deserted it for their homes in Panama. For most of the year the town is home only to merchant factors, artisans and tradesmen, servants, slaves, and soldiers. Approximately four hundred families live in Portobello year round.

Portobello Circa 1700, little changed from 1680.
Portobello Circa 1700, little changed from 1680.
Portobelo circa 1740, little changed from 1680.
Portobelo circa 1740, little changed from 1680.

The climate is hot and wet, and the east side of the city is “low and swampy.” When the tide is out, black mud and ooze is exposed at the edges of the town. It is considered an unhealthy place, and crews, soldiers, and passengers of the treasure galleons and Armada de Barlovento ships are often stricken with disease upon arrival. For this reason they call Portobelo Porto Malo. Others know it as an “open grave” that keeps the Capuchin and San Juan de Dios brother monks busy at their hospital when the Galeones treasure fleet is in during the Fair. Panthers are known to stalk the streets at night, carrying off livestock, dogs, and, it is said, even children at times.

After a heavy rain the streets are, according one visitor, “paved” with frogs and snakes. Nighttime is a cacophony of frogs and tropical sounds. In the nearby countryside are numerous plantations, most owned by “free Indians.”

Lionel Wafer describes Portobello as having “pretty Fair houses” roofed with red pantile, very Spanish in style. The town is divided into two major sections separated by narrow stream. Nearest La Gloria is the plaza de armas and market square surrounded by the governor’s house, treasury, customs house, a large church, and corps du garde, and behind them the great homes of the wealthy, usually empty of their owners except at the time of the Fair. In the other part of the town are storehouses along the bay, the Alcalde’s offices and jail, a great church, merchant

homes and artisan shops along the main street, and behind them probably slave or mestizo quarters. At the east end of the town is a large stable for hundreds of recua mules, and here are also probably either slave or poor mestizo quarters. The town is segregated by caste, as most Spanish towns on the Main are.

Forces: Roughly three hundred thirty buccaneers—two hundred fifty from mostly English crews, eighty from a mostly French crew—are ranged against an unknown number of Spanish regulars and militia, probably around three hundred. Some buccaneers are left behind to man their vessels.

The buccaneer commanders are:

  • Capt. John Coxon, commander-in-chief. He has a crew of roughly 100.
  • Capt. Robert Alliston, commanding the forlorn. He has a crew of roughly 25.
  • Capt. Cornelius Essex, commanding his company. His crew size is unknown.
  • Capt. Thomas Maggott/Mackett, commanding his company. He has a crew of roughly 20.
  • Capt. Jean Rose, commanding his French flibustiers. He has a crew of roughly 25.
  • Capt. Lessone, commanding 80 of his French flibustiers.
  • Absent: Capt. Bartholomew Sharp and his men, whose vessel is believed lost.
  • Absent: Capt. Edmund Cook, whose vessel is forced too far to windward.

Spanish forces consist of roughly two hundred to three hundred regulars and gunners, an estimated two hundred of which are infantry mosqueteros and arcabuseros, distributed among the two larger forts, the redoubt, and the corps du garde or blockhouse on the road to Panama. Militia forces and Native American allies, if any, are not listed. A Spanish document from Madrid, dated February 1680, confirms four compañías de infanteria with their commanders and officers at Portobello and Chagre, three of which are garrisoned at Portobello:

El Castillo de Santiago (la Gloria): company commanders Alferez José Julián Vaquerizo and Agustín de Aguirre, and their officers Andrés de Oviedo, Antonio de Leyva, and Miguel de Iturbide.

El Castillo de San Felipe: Alferez Antonio Balcón commanding, and his officers Luis de Paz y Olivares and Francisco Miguel de Angulo.

Portobello is defended by the large Castillo de Santiago, known commonly as La Gloria or, to the buccaneers, the Glory, adjacent to the town itself. It starts at the shoreline and ranges up the hillside, roughly 350 feet bottom to top, but its strength lies toward the bay—it is intended primarily to defend against attack by sea, not by land. Nearby in the shallows of the bay itself is the Fuerte de San Geronimo, a small redoubt with homes built on it but for the wall facing the sea and on which are mounted its few guns. It is almost certainly manned by the garrison of La Gloria.

La Castillo de Santiago or La Gloria, based on 17th century eyewitness depictions.
La Castillo de Santiago or La Gloria, based on 17th century eyewitness depictions.

Across the bay, at a point at the entrance, is the Castillo de San Felipe, a small to medium-sized fort. And across from it at the other point is a small corps du garde composed of one or two small buildings sitting along the road to Panama, one of them a blockhouse. (This blockhouse has been mis-named in some English documents as the Fuerte de Santiago, but period Spanish plans show definitively that La Gloria is the Castillo or Fuerte de Santiago.) The few soldiers who man it are to give warning of an attack from land or sea but, as is often the case

with sentries, they seem painfully unalert. Treasure ships typically anchor just outside the harbor, but their Armada de Barlovento escorts usually anchor just across from the town itself in order to aid in its defense. There are no treasure ships, guardas costas, or Armada de Barlovento men-of- war at Portobello when the buccaneers attack.

Historical Action: After a three-day, sixty mile trek, the buccaneers arrive at a Native American village three miles outside of Portobello, where, depending on the source, either a Native American man or a black man shouts “Ladrones!” (Thieves!) and races into Portobello to give warning. Commander-in-Chief John Coxon shouts, “good boyes, You that are able to runn get into towne before wee are descried!” But they cannot catch the fleet runner. Many of the buccaneers are exhausted from the sixty mile trek: hungry, and those who are barefooted have cut the soles of their feet on the many rocks they marched over.

Part of Portobelo in 1680 viewed from the sea, based on an eyewitness drawing.
Part of Portobelo in 1680 viewed from the sea, based on an eyewitness drawing.

Portobello’s population and defenders race into the great fort known as the Glory, as the buccaneer forlorn, led by Capt. Robert Alliston enters the town. All day the local population watches from the Gloria and other forts as the buccaneers sack the town. There is no defense the first day, but on day two, roughly two hundred regulars and militia sortie from the Gloria. The buccaneers engage them and force them back into the castle. After two days, the buccaneers withdraw, some by land with prisoners they hope to ransom, others with their best plunder in captured canoes. The buccaneers have no men killed in the attack, and only five or six wounded. The buccaneers rendezvous at a small key near the Bastimentos (“Provision Islands”) about three leagues distant, and await their vessels to take them off. Three days later, before the vessels arrive, roughly seven hundred Spanish regulars and militia from Portobello and Panama arrive, and fire at the buccaneers from shore. The buccaneers shift to another key for safety until their vessels arrive. Coxon orders a brief blockade of Portobello, which results in the capture a ninety- ton packet ship or navio de aviso from Cartagena.

The plunder from Portobello is meager: about 100 pieces-of-eight per man.

[Game Suggestions: The Spanish must either come out and fight or, as they did when Henry Morgan attacked, fire constantly on the attackers from the forts. If they descry the buccaneers early, they can engage them before they attack the town. If not, they must fight in the streets or from the fort. If they wait until the buccaneers have captured the town, they can only sally from the Glory—and the buccaneers will be waiting for them, as was the case historically. If the buccaneers are effectively fired upon from the forts, they will have to attack them.]

Spanish Map Circa 1700 Showing the Islas Bastimentos (C & D) at Left and Portobello at Right.
Spanish Map Circa 1700 Showing the Islas Bastimentos (C & D) at Left and Portobello at Right.