A Brief History of San Juan

The Safest Harbor

In 1508, when the Spanish Crown granted Juan Ponce de León permission to colonize Puerto Rico, the island’s first governor settled uncomfortably on the marshy banks of a small river in what is today the commercial Guaynabo district of the city. After several years of malaria outbreaks and harassment by Indians, he and a few dozen surviving settlers wisely began relocating in 1511 to a more defensible spear of land, what is now Old San Juan. Jutting out into the Atlantic Ocean and protecting a natural bay, the San Juan peninsula was quickly recognized for its potential as a military stronghold in the NewWorld. In 1533, Spanish reinforcements built La Fortaleza, which today functions as the governor’s seat, and six years later began construction of a massive fort – El Morro – at the peninsular tip, with ramparts up to 140 feet above the Atlantic Ocean, to guard over the entrance to the fledgling port.

Would-Be Conquerors

The scarcity of gold on the island failed to dissuade prospectors from stopping here, and soon the little port known as Puerto Rico (in the early days the name San Juan referred to the whole island) became a thriving supply and trade center for ore seekers en route to or from more remote regions of the Americas. Because of its location and protected harbor, it also became a “strong box” for Spanish gold in transit. Of course, this also made it irresistible to British, French and Dutch admirals in search of booty. In 1595 – only seven years after the defeat of the Spanish Armada off the British coast – the fearsome Sir Francis Drake attacked El Morro in what would be his last expedition. Frustrated by the firepower from the imposing fort, El Draque (as the Spanish called him) never gained a foothold on the island and died of plague aboard his ship soon afterwards. Three years later, Sir George Clifford, Count of Cumberland, laid siege to the city and managed to conquer some outlying areas, but was unable to take El Morro. Five months after the siege began, dysentery forced Clifford and his men to abandon their quest for the coveted port. The most devastating attack on San Juan came at the hands of Dutch General Boudewin Hendricks, who invaded the island by land with an overwhelming force in 1625. Though the Dutch quickly took over the city of San Juan, they too failed to crack El Morro, from which they were subject to constant counterattack. Without control of the fort, Henricks realized, there was no control of the island. Frustrated, the Dutch troops burned San Juan and left.

The City Walls

After the Dutch left it in ruins, King Philip IV of Spain ordered the fortification of the entire city. Soon, 42-foot-high walls of sandstone brick – with a thickness of up to 20 feet in some places – surrounded the peninsula, with a few entrances, such as Puerta de San Juan, built to withstand almost any attack. At the neck of the headland, Irish-born engineers employed by the Spanish king designed the ingenious Fuerte San Cristóbal to protect the city from land invasions. By 1771, one hundred years later, ramparts extended between the two forts, making what is now Old San Juan practically impregnable. The last major attack on the city, by British Lt. General Ralph Abercromby in 1797, was such a dismal failure that in the future foreign ships would simply avoid San Juan.

A royal dictate requiring San Juan to trade only with Spanish ships increased the isolation of the city from outside influences. And while San Juan was designated the first papal see in the NewWorld and remained a crucial stronghold of Spanish influence, rival cities such as Ponce and San Germán on the other side of the island thrived on smuggling and slowly sapped the economic strength of the capital. Waves of wealthy fugitives from revolutions in Haiti, the Dominican Republic, Venezuela and elsewhere breathed some new cultural life into San Juan during the 18th and 19th centuries. But by the end of the 19th century, the city represented fading Spanish power in the Americas, and the once-influential residents of this fortress city could only watch helplessly as events began to overtake them.

The American Century

After nearly 400 years, the only successful assault on El Morro ended with more of a whimper than a bang. Despite a few rounds of cannon fire between the old fort and US battleships, the heavy fighting of the 1898 Spanish-American War took place in Cuba. When it was over, defeated Spanish forces glumly handed over the keys to San Juan to the United States in a ceremony at La Fortaleza on October 18, 1898. At the time, the population of San Juan was estimated at about 12,000. Slowly at first, the city began to grow as North American influence opened it to increasing trade. World War II drew increased US attention to the strategic location of the island, and investment poured in from the north. It may have happened too fast. As poor farmers and agricultural workers flocked to San Juan to apply for new jobs offered by US-based manufacturers, roads and housing complexes spread at a pace that outstripped long-term planning efforts. North American residents and visitors preferred the beachside communities of Condado and Isla Verde, where they built high-rise luxury hotels that marked the beginning of the San Juan tourism industry. Moneyed East Coast residents seeking a sunny week away from the cold at home began to arrive in droves. These early visitors generally stayed within the confines of the all-inclusive hotels, however, and tourism revenues left the island almost as quickly as they arrived. Meanwhile, Old San Juan languished in terms of tourism, and until recently was better known for its seedy faded glory than as a classy, forward-thinking travel destination.

The Renaissance of San Juan

Since the late 20th century, the city of San Juan has undertaken an impressive face-lift of the historic quarter that could serve as a model for city planners everywhere. It goes well beyond the fresh coats of paint that brighten the pastel façades of the townhouses in Old San Juan. Ashford Avenue in Condado has undergone a major renovation, and an urban train is planned that should ease travel within Viejo San Juan. Ordinances against drinking in the streets, as well as proactive police efforts and noise and pollution control have changed the atmosphere from a rowdy town of students, pimps and drug dealers to a zone more conducive to families and tourists. The art galleries, restaurants, cafés, theme bars and shops that swell the storefronts help keep tourist revenues on the island. Cruise ship passengers by the thousands disembark to find a sparkling old city with restored colonial plazas and freshly washed cobblestones, with (as it’s often said) block for block more entertainment value than Manhattan. Old San Juan hasn’t completely lost its edge, though. The district around La Perla still teems with enough drug dealers and shady characters to entertain the most adventurous of night-prowlers. And the bars and small dance clubs still get wild on a Friday night.