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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.

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.

Capilla del Cristo (Chapel of Christ), is a small chapel located in the Old San Juan Historic District of Puerto Rico. Built in the 18th century, the structure has become a cultural icon of Puerto Rico and was saved from demolition in the 20th century. Most of the articles located at its altar are from 1753.

The chapel with its belfry is located in the Old San Juan Historic District in the western section of San Juan Islet, at the end of Cristo Street, now a pedestrian walkway. It sits on top of the old city walk. The chapel is a major tourist attraction in San Juan. Inside the chapel there is a famous painting called El Milagro ("The Miracle").

According to the legend, during a horse race that was taking place on the street where the chapel is located, a young rider and his horse took a bad fall and the rider went over the city wall but was miraculously saved. In a famous book about Puerto Rican legends, it says that the horse was killed but the rider lived. Afterwards, permission was granted to build the Catholic chapel and many festivals have been held, over the years, at the location to celebrate the miracle.

The chapel is open to publish on Saturday and Sunday from 12:00 to 18:00.

La Fortaleza, or the Fortress, is the current official residence of the Governor of Puerto Rico. Built between 1533 and 1540 to defend the harbor of San Juan, it is the oldest executive mansion in the New World. During the 1640 reconstruction, the chapel of Santa Catalina, then located outside the city walls, was demolished and integrated into the complex, which, upon that, assumed the new (current) name, Palacio de Santa Catalina.

La Fortaleza was the first defensive fortification built in San Juan, and the first of the series of military installations designed to protect the city, among which were the Fort San Felipe del Morro and Fort San Cristóbal. The construction was authorized by Charles V, the Holy Roman Emperor, as a defensive measure against the attacks from Carib Indians and the rivaling European powers.

The fortress underwent massive reconstruction in 1846 to convert from military use to a palatial residence. Since then, La Fortaleza has been the home to more than 170 governors of Puerto Rico and hosted various dignitaries, including President John F. Kennedy and his wife, Jacqueline Kennedy, who stayed here in 1961. At present, the complex consists of a few attached buildings with formal living quarters on the second floor, and private quarters on the third. The palace overlooks the high city walls fronting the bay, and its northern part contains sheltered gardens and a swimming pool.

The complex has been a UNESCO World Heritage Site since 1983 and as such may present definite interest to both history and architecture buffs with a taste for Spanish designs.

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.

Santa María Magdalena de Pazzis Cemetery is a colonial-era cemetery located in Old San Juan, Puerto Rico. It is the final resting place of many of Puerto Rico's most prominent natives and residents. Construction began in 1863 under the auspices of Ignacio Mascaro. The cemetery is located outside the walls of Fort San Felipe del Morro fortress, one of the island's most famous landmarks.

It was named in honor of Saint Maria Magdalena de Pazzi. The location of the cemetery is central to the Puerto Rican belief in the separation of death and life. The colonial Spanish government at the time the construction of the cemetery commenced, viewed death with fear because it was a mystery. Therefore, they decided to build the cemetery to overlook the Atlantic Ocean to symbolize the spirit's journey to cross over to the afterlife.

Located in the old Spanish Military Barracks, the Museum of the Americas is a multidisciplinary, multicultural, and multidimensional non-profit institution, established in 1992 by San Juan's famed archaeologist Ricardo Alegria. Its mission is to offer a synoptic vision of the history and culture of the American continent, with the main emphasis on Puerto Rico, through exhibition programs and cultural activities.

Dedicated to the American culture, the museum displays four permanent exhibits, namely: the Natives in the Americas; the African Legacy; Conquest and Colonization; and the Popular Arts. Additionally, there are some changing exhibitions as well, featuring paintings, carved and other sculptures, as well as many other works by artisans representing North, South, and Central America.

A true gem of curatorial design, to date the museum has hosted over 500 temporary exhibitions of art, history, and anthropology.

Tip:
The main language of the displays is Spanish, whereas some areas offer readable English translations. If you do not read Spanish, consider using the provided recorded audio tours.
It may take up to one and a half to two hours to explore all eight galleries. The museum closes at lunchtime, so plan accordingly.

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.

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.