Ask someone to name America’s oldest city and you’ll probably hear St. Augustine. Ask about America’s great historic fortifications and they may point toward the mainland. Ask where you’ll find the only tropical rainforest in the U.S. National Forest System, and suddenly the answers become less certain.
That’s where Puerto Rico enters the conversation.
Puerto Rico has been part of the United States since 1898, but its recorded European history stretches back centuries before the United States existed. That creates an interesting situation: once you stop treating “America” and “the continental United States” as interchangeable terms, some familiar historical rankings begin to change.
And some of them change dramatically.
Older Than Jamestown. Older Than Plymouth.
San Juan was established in its present location in 1521.
Think about that date for a moment.
Jamestown wouldn't be established until 1607. Plymouth followed in 1620. Even St. Augustine, Florida—the city usually introduced as America's oldest continuously inhabited European-founded settlement—was founded in 1565.
San Juan had already been there for 44 years.
But this isn't simply a competition over birthdays. San Juan and St. Augustine are actually fascinating historical siblings. Both were Spanish cities, both belonged to the same enormous imperial system, and both were positioned to defend Spain's interests in the Americas.
And San Juan's importance explains another Puerto Rican superlative.
A Fortress Built to Defend an Empire
Stand in front of Castillo San Felipe del Morro and it's difficult to appreciate its scale until you begin walking it.
Construction began in the 16th century, but Spain continued expanding and modifying San Juan's defenses for generations. The result was not merely a fort but an enormous defensive network guarding one of the Caribbean's most valuable harbors.
Those walls tell you something that maps sometimes don't:
Puerto Rico mattered.
European powers attacked it precisely because Spain considered it worth defending.
But Puerto Rico's unusual place within modern America isn't confined to history.
Leave San Juan, drive east into the mountains, and America suddenly becomes tropical.
America's Tropical Forest
El Yunque National Forest is the only tropical rainforest in the U.S. National Forest System.
Waterfalls, mountains, palms, giant ferns, coquí frogs and extraordinary rainfall don't exactly resemble the stereotypical image of an American national forest.
Yet there it is.
And then Puerto Rico's story gets even stranger.
Instead of looking backward five centuries, we can look upward—millions of miles into space.
When Puerto Rico Listened to the Universe
For 53 years, the enormous radio telescope at Arecibo was the largest single-aperture radio telescope on Earth.
Scientists used it to study planets, asteroids, pulsars and distant parts of the universe.
It became one of the most recognizable scientific instruments ever constructed—and even appeared in films and popular culture.
Then, in 2020, the telescope collapsed.
But its scientific legacy remains enormous.
And just a few miles away sits another structure that produces a completely different kind of reaction.
A 360-foot monument rising over northern Puerto Rico.
Yes, it's taller than the Statue of Liberty when Liberty's pedestal is included.
And that's where this week's episode gets particularly interesting.
Because once you start looking closely at Puerto Rico, you realize how many familiar statements about “the oldest,” “the largest,” or “the first” in America depend entirely on how someone defines America.
That distinction is the heart of this episode.
And because this is Chronicles & Cocktails, we're not discussing five centuries of empire, exploration, rainforests and giant telescopes without pouring something along the way.
Watch the Full Episode
In the new episode of Chronicles & Cocktails, we're putting the maps on the desk, pouring some Puerto Rican rum, and exploring some of the oldest, biggest, strangest and most surprising things found under U.S. jurisdiction.
Some you probably know.
At least one will probably make you say:
“Wait… that's in Puerto Rico?”
Watch: America’s Oldest, First, and Biggest… Are in Puerto Rico on Chronicles & Cocktails.
History. Travel. Culture. And, naturally, a cocktail.
Salud!