For other uses, see Battle of San Juan (disambiguation).

The Battle of San Juan was fought on 29 September 1625, and was an engagement of the Eighty Years' War. A Dutch expedition commanded by Boudewijn Hendricksz failed to seize after several months the island of Puerto Rico

Puerto Rico

Puerto Rico , officially the Commonwealth of Puerto Rico , is an unincorporated territory of the United States, located in the northeastern Caribbean, east of the Dominican Republic and west of both the United States Virgin Islands and the British Virgin Islands.Puerto Rico comprises an...

 from Spain.

Battle

Seventeen Dutch ships put sail to San Juan de Puerto Rico, whose Spanish governor — naval and military veteran Juan de Haro y Sanvitores - has been in office less than a month. Nevertheless, he prepares to receive the enemy as best he can, sending his predecessor, Juan de Vargas, to nearby Boquerón

Boquerón, Puerto Rico

Boquerón is a beach village located in the town of Cabo Rojo, Puerto Rico. The village is one of the main tourist attractions in the southwestern part of the island. As of the United States 2000 Census, the barrio population was 4,963....

 with militia to hinder any landings in Escambrón Inlet.

Yet Hendricksz implements a much bolder plan. At 1:00 P.M. the next day the entire Dutch fleet sails directly into San Juan’s harbor:

Roode Leeuw,Witte Leeuw, Leyden, Blauwe Leeuw, Goude Valck, Utrecht, Nieuw Nederlandt, Hoop van Dordrecht, Kleyne Tijger, Hoorn, Medemblik, Gouden Molen, Vlissingen, West Kappel, Goude Sonne, Koningin Hester, and Jonas.

They exchange shots with the harbor castle, inflicting superficial damage and killing four Spaniards, while gaining a safe anchorage within the roadstead off Puntilla Point, beyond range of de Haro’s artillery. However, shoals prevent an immediate disembarkation, allowing Spanish noncombatants to flee inland while the governor marshals his slender strength within San Felipe del Morro citadel

Fort San Felipe del Morro

Also known as Fort San Felipe del Morro or Morro Castle, is a 16th-century citadel located in San Juan, Puerto Rico.- Rundown :Lies on the northwestern-most point of the islet of San Juan, Puerto Rico...

. Six additional bronze 12-pounders are installed in its embrasures, 330 men gathering inside (220 effectives, but with abundant supplies).

On 26 September,Hendricksz leads 700–800 men ashore and occupies the empty city plus its smaller Cañuela Fortress two days later; the main citadel proves impossible to storm, so the Dutch begin digging saplines and installing a six-gun battery atop Calvario Heights by 29 September. At 9:00 A.M. the next day Hendricksz calls upon de Haro to surrender but is rejected, so action resumes. Capt. Jan Jasperz de Laet of West Kappel exits on 1 October to chase away a Spanish ship arriving with supplies, and on the night of Friday,3–4 October, the Spaniards sally out of their citadel in two companies of 40 men apiece under Capts. Sebastián de Avila and Andrés Botello, accomplishing little.

They enjoy better fortune at noon on 5 October, when 50 men under Capt. Juan de Amézquita y Quixano

Juan de Amezquita

Captain Juan de Amezquita , was a Puerto Rican soldier who defended Puerto Rico from an invasion by the Dutch in 1625. He fought and wounded Captain Balduino Enrico who was ordered by the Dutch Government to capture Puerto Rico.-Early years:Amezquita was born and raised in the town of San...

 destroy the advance Dutch works, killing a captain, a sergeant, and eight sappers. Guerrillas from the interior under Capt. Andrés Vázquez Botello de Carrera also begin plaguing the besiegers. On the night of 5 October they kill Nieuw Nederlandt’s captain and a 20-man boat party in the harbor; ten days later they destroy a similar force up Bayamón River

Río Bayamón

-History:Before this majestic river came to be what we all know and love today, it was but a mere puddle. As years went by, constant raining made it grow into a big lake. One day a meteor struck. The impact spread the water across the island and, after all that effort, it was reduced to a pond....

. By 16 October the guerrillas have grown so bold as to reconquer Cañuela Fortress, using two launches and 30 men to kill two of its Dutch occupiers, capturing another 14.
Faced with this increased pressure, Hendricksz finds himself trapped inside the harbor. Once more he calls upon de Haro to capitulate on 21 October, threatening to burn the city, but he is rebuffed. San Juan is therefore put to the torch, and the Dutch reembark at 10:00 A.M. the next day, hotly pursued by Puerto Rican units.The invaders must now run the gauntlet of Spanish artillery in order to escape, hesitating for a full fortnight before finally dashing past on 2 November.

The 30-gun, 450-ton Medemblik runs aground and is left behind for the exultant Spanish, Juan de Amézquita boarding and extinguishing the slow fuse that is burning toward its magazine. De Haro is unable to savor the victory because a cannon explodes near him during these final exchanges, spraying him with two dozen fragments and eventually causing his death. Hendricksz, meanwhile, retires into San Francisco Bay

San Francisco (Puerto Rico)

San Francisco is a sector within the township of Old San Juan in the capital of San Juan, Puerto Rico....

 for a month to recover from the setback. In addition to Medemblik, numerous other Dutch vessels have sustained damage, and 200 men have perished (as opposed to 17 Spanish fatalities during the siege). Hendricksz nonetheless detaches his five best vessels on a privateering cruise toward Santo Domingo

Santo Domingo

Santo Domingo, known officially as Santo Domingo de Guzmán, is the capital and largest city in the Dominican Republic. Its metropolitan population was 2,084,852 in 2003, and estimated at 3,294,385 in 2010. The city is located on the Caribbean Sea, at the mouth of the Ozama River...

 before attempting to lead his entire fleet west again in late November. Driven back by storms, he cruises south toward Isla Margarita

Isla Margarita

Margarita Island is the largest island of the state of Nueva Esparta in Venezuela, situated in the Caribbean Sea, off the northeastern coast of the country. The state also contains two other smaller islands: Coche and Cubagua. The capital city of Nueva Esparta is La Asunción, located in a river...

(Venezuela), despite advance warnings preceding him.