Columbus Square, originally known as Santiago Square, is one of the most important squares in San Juan, symbolizing progress and, at the same time, a testament to the old times. In the 17th century, the area marked the doorstep to the city, which was encircled by stone walls, from 1635-1641. The only way into the capital, back then, was through the five gates, the centermost of which was the Puerta de Santiago (or Land Gate), straddling the only highway linking the walled San Juan islet to the rest of Puerto Rico by land.

By 1772, the open space adjacent to Puerta de Santiago, while still unpaved, had taken the shape of Santiago Square. From 1862 to 1870, it was refurbished and the square finally started to take its current form. In 1893, the statue of Christopher Columbus was installed to commemorate the 400th anniversary of the discovery of Puerto Rico, following which the square itself was renamed Colón or Columbus Square.

To the south of it, today is the Tapia Theater, a true gem of Puerto Rican entertainment culture. Inaugurated in 1824, this lovely neoclassical structure was initially known as the San Juan Municipal Theater. Throughout the years, many notable performers have graced its stage. Outside the theater, along Fortaleza Street, there are a number of quaint restaurants and cute little cafes where one can sip some iced coffee outside whilst enjoying the sight of Columbus Square.

Proudly presiding over the bay of San Juan is the imposing La Fortaleza (Fortress), formally known as the Palace of Santa Catalina, the official residence of the Governor of Puerto Rico. The narrow road leading to the building, called Fortaleza Street, is the main artery of San Juan's historic quarter, cutting through most of it, and is also the oldest street in the area. It starts from Columbus Square and for the whole of its duration is lined with governmental buildings, hotels, perfumeries, craft shops, jewelry stores, and restaurants, gradually transforming into Avenue Juan Ponce de León in the east.

Just like many other colorful cobblestone streets in Old San Juan, each one more photogenic than the other, this thoroughfare is an important tourist attraction, in large part due to its historical and cultural significance. Visiting Fortaleza Street should be an integral part of every Old San Juan itinerary.

While the walled-in Old City has no shortage of vibrant photo spots, Fortaleza Street stands out above the rest due to the display of umbrellas – at the end of the street, near La Fortaleza itself – creating an overhead canopy that makes it particularly recognizable. These umbrellas tend to change colors during the year, from rainbow to all pink. Before the umbrellas, La Fortaleza Street was adorned with colorful kites.

The Monumento al Infante D. Henrique is a bronze statue of Prince Henry the Navigator, a 15th century Portuguese explorer and navigator who played a significant role in the Age of Discovery. The statue was created by Portuguese sculptor Leopoldo de Almeida, and was donated to the city of San Juan by the government of Portugal in 1958.

The monument serves as a tribute to the enduring friendship between Portugal and Puerto Rico, and is an important symbol of the shared history and cultural ties between the two nations. In addition to its historical and cultural significance, the Monumento al Infante D. Henrique is also a beloved landmark among locals and tourists alike, who come to admire its beauty and learn more about its history and significance.

No trip to San Juan is complete without a stroll along the beautiful Princess Promenade, a carefully restored historic landmark, one of the most visited in the capital. Built in 1853, this esplanade skirts the curved city walls on the southern side of Old San Juan and is quite picture-perfect, with the San Juan Bay on the one side and the impressive fortification walls on the other.

The Promenade is equally suited for both walking and people-watching. It is also a great place to visit for families with children – easily accessible and traffic-free. The abundance of trees here provides plenty of shade, and there are lots of artisan stalls and street vendors selling local food. The area also often hosts festivals and fairs on weekends.

From here, you can make a slight detour to the narrow path, known as Paseo El Morro, leading to the historic El Morro Fort and the nearby San Juan Gate, which is the only city gate remaining from the colonial period.

Princess Promenade gets its name from an old 1837 building, located here, known as La Princesa. Originally, this building served as a municipal prison, although presently it houses the headquarters of the Puerto Rico Tourism Company and an art gallery.

Built in the late 1700s, the San Juan Gate is a giant (40 feet high) structure, the last remaining of the original five gates carved into the three-mile wall that once surrounded the city. Today, the wall wraps around Old San Juan, from the cruise ship piers on San Juan Harbor to the capitol on the Atlantic.

Originally, each gate had a designated function. The red gate of San Juan played a symbolic role, serving as the main entrance to the city, and was named in honor of Saint John the Baptist. The first thing you notice approaching it is the inscription of The Sanctus ("Holy") hymn from the Catholic liturgy.

The city wall is the most enduring symbol of Puerto Rico and was built by the Spanish between 1539 and 1782. Made of sandstone, rubble, and mortar blocks – 20 feet thick, the wall measures 45 feet wide and 40 feet high in some parts and was meant to protect San Juan from invaders, notably the English, the Dutch, and the Americans. Its iconic sentry boxes now symbolize the island's Spanish heritage and resilience in an ever-changing world.

Nearly impenetrable to foreign attack, the city wall proved defenseless, nonetheless, against modern automobile traffic, pollution, and misguided attempts to preserve it that have seriously endangered the wall, leaving it crumbling in some places.

Currently a National Historic Site, the city wall is maintained by the National Park Service which attempts to recreate the magic mixture of sand, water, and limestone that was once used to stucco the wall. Along with the adjoining fortresses of El Morro and San Cristóbal, the city wall attracts 1.2 million visitors each year.

Tip:
As you walk through the gate, just pause for a second and notice how thick the walls really are. Also, check out the street vendors outside, on the corner, offering refreshments including Puerto Ricans' favorite, piragua.

Arms Square is the de-facto central square of San Juan. Over the years, it has changed several names relative to the functions it served. Initially, in 1521, it was called Vegetables Square. Then, during the 17th-19th centuries, it was known as Arms Square, for being the grounds for military drills. After that, in the early 20th century, it turned back to being called Vegetables Square once again, serving as a marketplace, before it finally re-assumed the Arms Square title.

The plaza is modeled on the classic squares of Madrid and Mexico City. Although it factually existed for centuries, it was not until 1840 that the city council approved its proper development, which started in 1851. It was at that time that the four bronze statues, oil-coated to simulate marble, representing Commerce, Industry, Science, and the Arts, arrived here (there were a total of eight statues to be installed, but the other four were lost). In 1872, the original statues were replaced with the new marble ones, representing the Four Seasons, put in the four corners of the square.

In 1955, two circular fountains and two lampposts in the center were added. The four statues were then configured in a circular fountain outside the Palacio de la Real Intendencia, which is the seat of the Department of State of Puerto Rico, on the western side of the square.

A highlight of the northern side is the Casa Alcaldía – home of the San Juan City Hall. Built in 1789, this Spanish colonial-style edifice with twin turrets resembles its sister building in Madrid. The tinkling of the fountain, the comfortable seating in the shade of the trees, and the presence of several old-style coffee booths selling snacks have long attracted tourists as a good spot for a sightseeing break when you can stretch out your feet and soak up some of the everyday comings and goings.

The laid-back atmosphere of the place also made it a popular gathering venue with locals, offering a chance to buy kids some traditional treats (like sesame-seed lollipops or coconut candies), watch shows, play dominoes, or chit-chat with friends.

The Cathedral of San Juan Bautista is the Roman Catholic temple and the seat of the Archdiocese of San Juan de Puerto Rico. This is one of the oldest buildings in San Juan and the second-oldest operational church in the Americas. Traditionally, travelers entering San Juan Gate would make this cathedral their first stop in the city to thank God for their safe journey.

It sits on the site of a grammar school, established in 1513 by Bishop Alonso Manso. This was the first school in Puerto Rico (and the oldest school in the United States after Puerto Rico became a US territory). Here, the Latin language, literature, history, science, art, philosophy, and theology were taught free of charge.

The very first, wooden, church on this spot was built in 1521. It was destroyed by a hurricane, and the current temple of stone was built in its place, in 1540. The church was remodeled several times over the course of centuries, most recently in 1917.

The cathedral contains the tomb of the Spanish explorer Juan Ponce de León. It also houses a shrine dedicated to the Blessed Carlos Manuel Rodríguez Santiago, the first Puerto Rican and the first Caribbean-born layperson (much as the first layperson in the history of the United States) to be beatified.

The Cathedral of San Juan Bautista is also unique as a rare example of medieval Spanish architecture in the New World.

The Fort San Felipe del Morro, or simply El Morro, is a 16th-century citadel on the northwestern tip of the San Juan islet, named in honor of King Philip II of Spain. It was the second military installation, after La Fortaleza, built in what is now known as the Old Town.

The construction began in 1539, authorized by King Charles V, and was finished in 1790. During that period, El Morro had been transformed from a promontory mounted with a cannon to a six-level fortress designed to guard the entrance to the bay of San Juan from seaborne invaders. Many more structures were added to the complex over the next 400 years; the outer walls, built initially 6 feet (1.8 m) thick, were augmented to 18 feet (5.5 m) by the end of the 18th century.

Thanks to El Morro, the Spanish were able to defend Puerto Rico from invasions by the British and the Dutch, as well as pirates. In 1898, following the Spanish-American War, the island changed hands from Spain to the United States. El Morro was actively used as a military installation during the First and Second World Wars.

In 1961, the US Army retired El Morro, passing it on to the National Park Service to use it as a museum. In 1983, El Morro and the walled city of Old San Juan were declared UNESCO World Heritage Sites.

Tips:
A ticket to El Morro allows entry to the Castillo San Cristóbal (and vice versa) for a single fee.