Erstwhile colonial seat and mid-century destination for the Hollywood elite, San Juan is a city where rich food, good times, and reminders of the past are always just around the corner—nowhere more so than at the Caribe Hilton.
It’s 1949 and Conrad Hilton Jr. is experiencing one of his most memorable years yet. In the fall he meets teenage starlet Elizabeth Taylor, and he is wooed by her beauty as much as he woos her with his charm. Hilton and Taylor are at the epicenter of Hollywood glamor, he the burgeoning hotelier set to inherit a dynasty, and she a siren of the silver screen. Later that year Hilton would unveil a new endeavor that would pitch the already enraptured media into fresh frenzies of ecstasy: the Caribe Hilton, his family’s eponymous chain’s first ever “international” hotel, and the first modern luxury hotel in Puerto Rico, situated at the edge of historic Old San Juan.
The Caribe Hilton was the product of a $7.4 million investment from the Puerto Rican government and the Hilton family’s ambition to see their business truly become a destination for the rich, famous, and, most importantly, the oh so glamorous. Historically, sugarcane, coffee, tobacco, and spices were Puerto Rico’s major exports, but with the opening of San Juan’s Condado Vanderbilt Hotel in 1919 the island experienced a paradigm shift in how it understood its economy. By 1947 the island’s government realized that tourism would be the next great resource that Puerto Rico had to offer. With Old San Juan—a district of the capital city teeming with architectural vestiges of sixteenth-century Spanish colonialism and boasting a rich indigenous-inflected cuisine—now playing host to the most cutting edge, modern hotel the island had ever seen, Hilton and Puerto Rico were poised to make history.
The glamor came, and history they made. In December 1949 the Caribe Hilton opened. Flashy glitz was never in short supply at this ritzy, beachside retreat. Starlets, titans of industry, and socialites were the first of the hotel’s clientele, but despite its luxury branding, the Caribe Hilton’s design was quite egalitarian, with every room in the building offering an ocean view. The hotel’s style was meant to be distinctly Puerto Rican. The brainchild of Puerto Rican architectural firm Toro, Ferrer, and Torregrosa, the hotel was the pinnacle of the firm’s “tropical modernism” style, incorporating an open lobby that functioned as a breezeway for cooling the structure and landscaping with palm trees native to the island.
Rising in the shadow of Old San Juan, this new Hilton location served as a character foil to the history of the island. But with a seventy-fifth birthday under its belt, the once state-of-the-art hotel is now a nostalgic resort, still a destination of style and starlets, but joining the ranks of historic Puerto Rico.
San Juan Bautista (shortened to San Juan in the 1520s) was the name by which the entire island was known in 1508 when Spanish conquistador Juan Ponce de León—explorer of fountain-of-youth fame—established its first settlement and colonial capital, Caparra. When this city proved inhospitable, a new capital city was established by the Spanish colonists a few miles to the north, on what is now San Juan Bay, in 1521. According to Pablo García Smith, a guide for The Spoon Experience who is known affectionately to many as “WikiPablo” for his incredible breadth of knowledge of culinary and cultural history, the island’s identity is closely tied to its homages to St. John the Baptist, who, aside from being the capital city’s namesake and that of its five-hundred- year-old cathedral, has a colorful midsummer festival dedicated to him, and inspired the Puerto Rican custom of diving into the sea three times on the eve of his birth. But as a puerto rico—“rich port”—with strategic military positioning and tradeable natural resources that quite literally spiced up European life, Smith says, the island’s economic importance came to overshadow its reputation for religious zeal. And so, in time, the name San Juan came to be used for just the capital, while the island as a whole became Puerto Rico, shorthand for its importance to the Spanish, English, and Netherlandish empires that vied to control it.
Today, San Juan’s seascape is still stalwartly surrounded by remnants of colonial fortifications. The Castillo San Cristóbal, constructed between 1634 and 1790, was the largest Spanish fort in the American colonies at the time of construction; Castillo San Felipe del Morro, which was begun in 1539, would take 250 years to complete. Both castles are icons, and, along with Ponce de León’s Casa Blanca, his white house, and La Fortaleza, completed in 1540 and serving to this day as the governor’s mansion, are among the oldest buildings on the island.
European powers would lose this foothold in the Caribbean in 1898. A bargaining chip once more in an international ecosystem of conquest, economy, and culture, Puerto Rico would be ceded to the United States after the Spanish-American War. Only half a century after American territorialization, this “rich port” would host a new roster of cultural commanders. The Caribe Hilton’s creation was a watershed moment that proved formative to Puerto Rico’s economy and politics. People involved at all levels of the hotel’s creation made their mark on the historic landscape of Puerto Rico in the twentieth century, including Roberto Sánchez Vilella, known to world history as the island’s second elected governor, but in Caribe history as its resident engineer. The Caribe Hilton played host to a number of people who counted themselves among Hollywood glitterati throughout the 1950s and ’60s—due in part to publicity from Hilton Jr.’s marriage to Taylor in the spring of 1950, and the couple’s honeymoon at Hilton’s international triumph—cementing the Caribe Hilton’s reputation as a star-studded destination, rather than just a grand hospitality experiment. Rita Moreno, Gloria Swanson, and swimmer Gertrude Ederle were all among the Caribe Hilton’s first guests. They and other worthies would swim in the hotel’s kidney-shaped pool, take in the salt air from beachside cabanas, and sip on the now-famous piña colada, a drink whose invention the Caribe Hilton lays claim to.
Though Hilton and Taylor’s marriage was brief (205 days to be exact), the site of their romance, the Caribe Hilton, endures as a testament to that moment, and as a tropical bastion of mid-century retro. Today the hotel embraces its vintage roots, understanding itself as a part of the fabric of Puerto Rico’s history as much as Juan Ponce De León.
SHARON KONG-PERRING is a travel journalist and PhD candidate at Birmingham City University whose forthcoming books include The Bloomsbury Handbook of Gender in Popular Music, to be published in 2026.
