San Juan, Puerto Rico, is one of the most historic metropolises in the Americas. Founded over five centuries ago, it has played a key 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 moved 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 in the region, 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 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 in 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, particularly the patriotic movements that swept through nearly all the neighboring colonies. In fact, San Juan 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, however. 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 have especially enjoyed visiting the city due to the many historical landmarks that reside throughout. 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.

Among the stunning architectural features that Warren and Whitmore incorporated into the Condado Vanderbilt Hotel’s appearance included gorgeous white walls and red tiling that seemed to glisten from the natural light that radiated off the sea. French-inspired windows and lofty ceilings made the interiors feel spacious, yet warm. All the public spaces had unique motifs like ornate marble and intricate mosaics. A grand staircase extended up into the hotel’s upper floors, where 98 luxurious guestrooms that came complete with their own private bathrooms and oceanside views. Much of the architectural features incorporated by Warren and Whitmore were inspired from Spanish Colonial Revival design principles. Also known as “Spanish Eclectic,” this architectural form is a representation of themes typically seen in early Spanish colonial settlements. Original Spanish colonial architecture borrowed its design principles from Moorish, Renaissance, and Byzantine forms, which made it incredibly decorative and ornate. The general layout of those structures called for a central courtyard, as well as thick stucco walls that could endure Latin America’s diverse climate. Among the most recognizable features within those colonial buildings involved heavy carved doors, spiraled columns, and gabled red-tile roofs. Architect Bertram Goodhue was the first to widely popularize Spanish Colonial architecture in the United States, spawning a movement to incorporate the style more broadly in American culture at the beginning of the 20th century. Goodhue received a platform for his designs at the Panama-California Exposition of 1915, in which Spanish Colonial architecture was exposed to a national audience for the first time. His push to preserve the form led to a revivalist movement that saw widespread use of Spanish Colonial architecture throughout the country, specifically in California and Florida. Spanish Colonial Revival-style architecture reached its zenith during the early 1930s, although a few American businesspeople continued to embrace the form well into the late 20th century.

Charles Lindbergh, legendary aviator who completed the first solo transatlantic flight in world history.

Carlos Gardel, singer who was the most prominent figure in the history of the tango.

Errol Flynn, actor known for such roles in Captain Blood, The Charge of the Light Brigade, and The Adventures of Robin Hood.

Bob Hope, comedian and patron of the United Service Organization (USO). 

Arthur Rubinstein, classical pianist regarded as the greatest Chopin interpreter of his time.

José Luis Moneró, musician from Puerto Rico best remembered for his performances with bands like Siboney.

Eleanor Roosevelt, First Lady of former U.S. President Franklin Delano Roosevelt (1933 – 1945) 

Franklin Delano Roosevelt, 32nd President of the United States.

John F. Kennedy, 35th President of the United States (1961 – 1963)

Eleanor Roosevelt: The Condado Vanderbilt Hotel has hosted countless luminaries throughout its history, ranging from Hollywood celebrities to notable politicians. Among those illustrious individuals who stayed at the inn was former First Lady Eleanor Roosevelt. She was born Anna Eleanor Roosevelt in 1884, the daughter of Elliott and Anna Hall Roosevelt. A member of the Oyster Bay clan of the Roosevelt dynasty, Elliott himself was the brother of U.S. President Theodore Roosevelt. Roosevelt’s immediate family cherished community service, although both her parents died at an early age. Her intellectually progressive outlook on life was further reinforced by Marie Souvestre, who was Roosevelt’s headmistress during her time in London’s prestigious Allenswood Boarding Academy. Nevertheless, she kept those personal influences close to her heart, and used them as the foundation for her future work as a social activist. Indeed, some of her earliest work involved tending to the overcrowded settlement houses in New York City’s Lower East Side.

Around the same time, she began courting her distant cousin, Franklin Delano Roosevelt. They eventually married in 1905 and had six children together. Yet, the marriage was strained by the two’s dueling personalities, as well as the demands of her husband’s early political career. Roosevelt often felt her responsibilities as a “political wife” were tedious, especially after Franklin’s appointment as the Assistant Secretary of War shortly before the outbreak of World War I. Their marriage further deteriorated in 1918, when Eleanor discovered that Franklin had an affair with their mutual friend, Lucy Mercer. Roosevelt, thus, vowed to throw herself fully back into her political activism. But the two had a strong understanding that their fates remained intertwined and aspired to support one another going forward. It was Eleanor who encouraged Franklin to remain in politics even after he was beset with polio in 1921. As such, Eleanor Roosevelt was incredibly instrumental in aiding her husband’s election as the Governor of New York in 1928, as well as his subsequent rise to the presidency four years later. She often gave numerous speeches in public on his behalf that galvanized thousands of people. Roosevelt also became a central figure at of his many campaign events, serving as her husband’s voice whenever he could not attend.

But Eleanor Roosevelt still established her own vibrant political career as the First Lady of the United States. Historians today consider her actions to have fundamentally transformed the role that the First Lady traditionally held within the national government. Roosevelt used her position to advance a number of causes close to her heart, including gender equality, civil rights, and housing reform. For instance, she arranged a massive celebration at the nearby Lincoln Memorial to protest the racist decision of the Daughters of the American Revolution to not let Marian Anderson—an African American opera singer—perform at Constitution Hall. On another occasion, she privately lobbied for the passage of the Costigan-Wagner Bill, which would have made lynching a federal crime. Roosevelt also held exclusive press conferences at the White House for female journalists, in order to help enable women to break into the field. She even attempted to create an experimental community in West Virginia called “Arthurdale,” where homeless miners unfairly driven out of the industry would have a shot at achieving a new, independent life. Although considered a failure, it was testimony to her commitment to enhance the lives of countless others.

Eleanor Roosevelt’s historic career continued well after her time as the nation’s First Lady ended in 1945. She played a significant role in transforming Hyde Park into a museum dedicated to her late husband’s legacy, which set the precedent for future presidential libraries to follow. She also served as a delegate to the United Nations Commission on Human Rights, becoming its chairperson in 1947. Roosevelt remained with the organization until 1953, and her political insight proved integral toward drafting the Universal Declaration of Human Rights. After working to reform New York politics throughout the remainder of the decade, Roosevelt eventually worked to support the campaign of John F. Kennedy. While she initially rebuffed Kennedy for his refusal to denounce McCarthyism, Roosevelt relented on the grounds that she believed he had the best chance of leading the nation into the future at the time. When Kennedy won in 1960, she became his representative to such organizations like the National Advisory Committee to the Peace Corps. Then, in 1961, Kennedy appointed her as the First Chair of the Presidential Commission on the Status of Women. But Roosevelt would not see the commission come to fruition, as she died mere months after it was organized. Eleanor Roosevelt has since been revered as one of the most influential figures in 20th-century American history and is esteemed throughout the world today for her years of advocacy.