San Juan, Puerto Rico, is one of the most historic metropolises in the Americas. Founded over five centuries ago, it has played an important role in the history of the so-called “New World.” Its first inhabitants arrived in 1508 under Juan Ponce de León—a conquistador now mainly remembered for his ill-fated explorations to find the “Fountain of Youth” in Florida. Calling the settlement “Caparra,” he specifically chose a nearly landlocked harbor along Puerto Rico’s northern coast to serve as its location. But Spanish colonial officials later relocated the settlement to an inlet a few miles to the east and rechristened it as the “Ciudad de Puerto Rico.” Juan Ponce de León also continued to call the community home, having served as the island’s governor shortly before the town’s relocation. Juan Ponce de León and his family lived inside a beautiful estate known among the locals as “Casa Blanca.” San Juan’s location quickly made it one of Spain’s most important seaports in the Caribbean, with its wharves ferrying all kinds of goods and people across the Atlantic. The city even became a major marshaling point for Spanish incursions into mainland North and South America. San Juan gradually assumed great political significance in Spain’s global empire, as well. The city specifically served as the Catholic Church’s first headquarters on the other side of the Atlantic, as well as at the seat for one of its bishops. Unfortunately, this newfound prosperity attracted the attention of Europe’s other major superpowers, who attempted to conquer San Juan and the rest of Puerto Rico over the next 300 years. Those nations legalized pirating against the naval traffic heading into San Juan, which culminated in numerous raids on the city itself. Some of the most famous assaults transpired under famous buccaneers like Francis Drake and George Clifford. Spain’s rivals also tried to directly capture the city with their own navies on several occasions, too. Indeed, the Dutch and the British sent fleets against San Juan in both the 17th and 18th centuries, respectively.

To deter those aggressive threats, the Spanish constructed many forts across San Juan. The most noteworthy of those defenses were a fortified castles known as “La Fortaleza” and “San Felipe del Morro.” Yet, the most imposing citadel was the mighty “San Cristóbal.” The largest Spanish fort in the Western Hemisphere, it made San Juan one of the most heavily protected cities throughout the entire world. Nevertheless, San Juan’s status as an influential colonial city gradually decline as other places like Mexico City and Lima grew in stature. San Juan thus remained relatively isolated from the greater politics of the Spanish Empire by the 19th century, especially the patriotic movements that swept through nearly all the neighboring colonies. In fact, Puerto Rico was a bastion for the many loyalists that had fled from the Spanish American Wars of Independence. Puerto Rico as a whole remained part of Spain’s diminishing empire in the wake of the conflicts, becoming one of its last oversees colonial territories. Spain’s sovereignty over the entire island finally came to an end during the Spanish-American War of 1898. San Juan itself did not experience any significant fighting, although the guns at San Cristóbal did briefly engage with a flotilla of United States Navy ships anchored just off the coast. Now a territorial capital within the United States, San Juan gradually evolved into a modern metropolis. While early economic growth was slow, numerous industries soon emerged throughout the city toward the latter half of the 20th century. San Juan also maintained its local political importance, too, as it remained Puerto Rico’s capital after it obtained self-governance in 1952. Today, San Juan is among the most popular tourist destinations throughout the Caribbean. Cultural heritage travelers in particular have enjoyed visiting modern-day San Juan, due to the many historical landmarks that reside in the city. In fact, much of San Juna’s historic core—known as “Viejo San Juan” or “Old San Juan”—is even identified as both a U.S. National Historic Landmark and a UNESCO World Heritage Site.

Originally an ancient convent, El Convento Hotel still displays the same Spanish colonial architectural aesthetics that first defined it years ago. Also known today as “Spanish Eclectic,” Spanish colonial architecture dates back centuries and is one of the most prolific design aesthetics seen throughout the Americas today. The form itself emerged when the first generations of Spanish colonists began arriving from Europe at the start of the 16th century. Seeking to establish similar settlements to the ones found in their native Spain, the pioneers began to essentially recreate European cities across Mexico. Many of the earliest settlers crafted buildings that combined elements of architectural motifs popular in Spain at the time, including Renaissance, Moorish, and Byzantine forms. Over time, though, those beautiful and extravagant styles were complemented by other, newer forms, such as Neoclassical and Baroque architecture. The amalgamation of all those unique styles eventually produced structures that were incredibly decorative and ornate. But despite the variety in their appearance, they mostly shared the same general layout and qualities. For instance, the buildings typically featured a central courtyard, as well as thick stucco walls that could endure diverse climate of both North and South America. Among the other recognizable features that they possessed included heavy carved doors, spiraled columns, and gabled red-tile roofs, as well. This new stunning architectural form soon defined the landscape of countless Spanish cities in the “New World,” such as Mexico City, Lima, and of course, San Juan. Many of those buildings still survive to this day, too, with some even preserved as recognized UNESCO World Heritage Sites

Rita Hayworth, actress remembered for her roles in films like Gilda, Cover Girl, and The Lady from Shanghai.

Pablo Casals, remembered today as one of the preeminent cellists of the 20th century.

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Gloria Vanderbilt, renowned artist, author, and fashion designer known for her work popularizing designer blue jeans.