The Western Hemisphere’s Oldest City Has Lots to Offer

By Dana Armstrong

The Caribbean has become one of the most popular destinations for American tourists during the COVID-19 pandemic, and there is one island that has fared especially well: Puerto Rico.

According to Discover Puerto Rico, the island welcomed 553,554 airport arrivals in July 2021 alone. The majority of those flights departed from Orlando, Florida, making the Orlando-San Juan route the busiest international route in the world.

With Puerto Rico’s picturesque beaches, care for COVID-19 precautions (as of September 2021 two-thirds of the island’s residents are fully vaccinated), historic sights, and exciting new venues, it’s not hard to understand the appeal.

Plus, the city is celebrating its 500^th anniversary this year — making it the oldest city in the Western hemisphere!

Here is a guide to the old and new of San Juan and the ways you can become involved with the city’s 500-year anniversary festivities.

A Brief History of San Juan

Before the city was known as San Juan, it was actually named Puerto Rico, or “rich port.” Juan Ponce de Leon founded the city in 1521, just 28 years after Christopher Columbus discovered the island’s shores. However, the indigenous Taíno were the island’s first inhabitants.

Claiming the island as a Spanish colony, Columbus named the island San Juan after John the Baptist. The city and country names swapped places later in the 1520s. The island remained a Spanish territory until the 1898 Treaty of Paris. Then, it fell under the rule of America.

From 1952 to the present day, the island has been a US Commonwealth. It is difficult to find consensus among locals and international onlookers on whether independence or remaining a commonwealth is better. Nevertheless, the appeal to Americans as a tourist destination is undeniable.

San Juan’s Beginnings

San Juan is the capital of Puerto Rico and, as the oldest city in the Western Hemisphere, it offers an array of historic destinations to visit. They are all located within a convenient walking distance in Old San Juan.

Casa Blanca Museum was once the residence of Juan Ponce de Leon’s family (Juan died before he could occupy it). As it was built in 1521, it is said to be the oldest remaining residence in San Juan. The residence now operates as a museum, and guests can tour its gardens and learn more about the 16^th and 17th-century artifacts within.

A six-minute stroll southeast will take you to another one of the city’s important white buildings: the San Juan Bautista Cathedral. Though the original 1521 church was destroyed by a hurricane, the “current” building still dates back to 1540.

According to Kenya Mavhera, a press representative for Puerto Rico, “it houses the remains of Juan Ponce de Leon, the mummified remains of Saint Pius (a first-century Roman martyr), and the oldest spiral staircase in America, with 88 steps leading to the church bell tower.”

The cathedral is open every weekday to visitors.

San Juan’s Military Past

Puerto Rico was once valued for its abundance of natural resources – including sugar, tobacco, coffee, and gold – and livestock-raising opportunities.

Therefore, it captured the interest of other European countries looking to conquer and cash in. The Spanish needed forts to protect the island.

The Castillo San Felipe del Morro (or El Morro) is the island’s undefeated fortress. It looms high over the sea for an advantageous view and took 250 years of construction to transform into the six-level structure you see today.

The US Army retired the fortress in 1961 to instead be used as a museum. Guests can learn all about its extensive use – from a 1595 attack from Sir Francis Drake to it having a military base status during World War II – inside.

Constructed just a year after El Morro is La Fortaleza (literally named “the fortress”) in Old San Juan. After numerous failures at protecting San Juan from enemy attacks, the building was remodeled in 1846 and switched roles.

It is now a working government building that has also served as the residence for 170 of Puerto Rico’s governors. Make sure to call ahead to see if you can join a guided tour of the house and gardens.

The Many Lives of the Hotel El Convento

To make the most out of your stay and be conveniently located in the heart of Old San Juan, consider lodging at the Hotel El Convento. The hotel provides all the modern luxury you could desire from $159 – $631 per night with the charm of being a 1646 building.

Before it was a hotel, Carmelite nuns lived and studied there until 1903. That explains its placement just across from the San Juan Bautista Cathedral. Then, it became a retail store and dance hall before converting into a hotel in 1962.

Why pass up the opportunity to stay in the Historic Hotels of America’s oldest location? Find out more information and book your reservation here.

Arts and Entertainment for All

San Juan is transforming into an entertainment hotspot. Whether for a night of art gallery viewing, dancing away your worries, or watching a performance, you are sure to keep busy.

The 1832 Teatro Tapia, named after Puerto Rican playwright Alejandro Tapia y Rivera, is the oldest continually used theater in the US. Its impressive theater with three levels of seating can accommodate 640 guests.

Watch plays, concerts, dance performances, and stand-up comedy shows from the comfort of its luxurious red velour seats.

Distrito T-Mobile: New in San Juan

But for a more modern take on San Juan, try out Distrito T-Mobile, which opened in August 2021. According to Mavhera, the five-acre area “combines the best in global retail, destination dining, art, entertainment, music, technology, and hospitality.”

Watch a game on Arena Medalla’s 30-foot LED panoramic screens over a glass of authentic Puerto Rican rum. Or, take the family to ToroVerde Urban Park for ziplining, a ropes course, and an arcade. Coca Cola Music Hall is sure to provide quality night entertainment, and you can wind down after in one of Aloft San Juan’s modern suites.

Also, make sure to visit the Museum of Contemporary Art which cycles through an array of exhibits every year. The museum aims to showcase the 20th-century contributions of Puerto Rican, Caribbean, and Latin American artists.

Join San Juan’s 500-Year Festivities

Leah Chandler is Discover Puerto Rico’s Chief Marketing Officer. She says, “During this year-long commemoration [celebrating 500 years of San Juan], we encourage visitors to discover the island’s vibrant culture, storied past, and beautiful people through various events and celebrations to mark this significant milestone.”

Specialized two-and-a-half-hour walking tours of Old San Juan are running now and will guide you through the city’s historic sights. Additionally, make sure to keep up-to-date with the 500 years of San Juan website which will soon release its calendar of events running through 2022. Look forward to “cultural events, exhibitions related to historical events, concerts, and other shows.”

It’s never been a more exciting time to discover the old and new of San Juan, Puerto Rico.