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.

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.

Casa Blanca is a house museum located in Old San Juan. This lovely white adobe building is one of the oldest buildings in San Juan. Built in 1521 it served as the first fortification of the San Juan islet and residence for Juan Ponce de Leon, the first governor of Puerto Rico, and his family. Juan Ponce de Leon unfortunately died in an expedition to Florida without ever lived in the house. It was later used as the residence of his descendants, until the mid-18th century. As a fortification it served mostly as a refuge in times of attack from Taino rebels.

The house was built in wood but the original structure was destroyed by fire and rebuilt in stone and masonry. It subsequently was occupied by members of the Spanish army and later by American army commanders. The surrounding gardens were planted by the first American governor of the island in the 19th century. In 1967 the complex was transferred to the government of Puerto Rico and declared a historical monument. In 1981, it was recorded in the Historic American Buildings Survey. The house is a museum of 16th and 17th century artifacts managed by the Institute of Puerto Rican Culture.

The building, walls and gardens are in excellent condition. The plaques on the walls explain the history of each room. The museum charges a small fee ($5) to enter while one can visit the gardens for free.

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.

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.

San Jose Church (Iglesia de San Jose), located in Old San Juan, is one of the first significant works of architecture on the island. The church was first opened in 1532 and is one of the earliest surviving examples of 16th-century Spanish Gothic architecture in the Western hemisphere.

Juan Ponce de León, the first governor of Puerto Rico, was buried in the crypt of the church from 1559 to 1836, when his remains were exhumed and later transferred to the Cathedral of San Juan Bautista. However, his coat of arms is still located near the main altar. His grandson, Juan Ponce de Leon II is buried in the crypt beneath the Sanctuary's floor. Puerto Rican painter José Campeche is also buried in the church.

In 2002, a restoration project on the structure began and several painted murals were discovered including a mid-19th century depiction of the Battle of Lepanto. In 2004, the church was listed on the 2004 World Monuments Watch by the World Monuments Fund, which helped the conservation effort.

The Church of Saint Joseph is closed to visitors due to the restoration work that has been going on. It is expected to re-open in 2020.

The Spanish brought them back to Spain from Puerto Rico and called them “cigarillos.” Cigar making is still considered an art form in Puerto Rico. Until the late 1950’s, Puerto Rico was among the world’s largest tobacco exporters but the industry has since declined.

There is a variety of Puerto Rican made cigars, but one of the oldest and most well-known brands from the island is Don Collins. Don Collins cigars are handmade in the oldest surviving cigar factory in the Caribbean. The factory, which dates back to 1506, is available for tours. But you don’t have to go to the factory to take in the aroma of the famed tobacco, just walk into any one of the tobacco shops in San Juan or you can head straight to the Don Collins shop.

Don Collins cigars use 13 different kinds of Puerto Rican grown tobacco produced by independent farmers on the island. A Lonsdale bundle will run you about $140.00 while a bundle of Puros Indios costs $225.00. But if you want to try a few different ones, sample packs are available ranging in price from about $40 - $70 depending on how many cigars per pack. Price: $2-$17 per cigar.

What to buy here: Puerto Rican Cigars.

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.

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.

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.

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.

Standing guard at the eastern gate, north of Columbus Square, is an imposing 18th-century fortress, called San Cristóbal. Contrary to her sister, El Morro, which was designed to protect from attacks by sea, the San Cristóbal Fort guarded the city against the enemy approaching by land, for which purpose it created a crossfire with El Morro over the bay. The citadel construction began in 1634 and was meant to strengthen the Spanish position in the face of imminent English and Dutch invasion.

The fort was named San Cristóbal in celebration of the Spanish victories which enabled ejecting of the English and Dutch interlopers from the island of the same name in the Lesser Antilles, which was then part of the insular territorial glacis of Puerto Rico.

When finished in 1783, the Fort San Cristóbal covered nearly 27 acres of land and practically wrapped around the whole of San Juan, with the entry to the city sealed by the San Cristóbal's double gates. After almost 100 years of relative peace, about a third of the fortification was demolished, in 1897, to help ease the flow of traffic in and out of the walled city.

The Fort San Cristóbal is now a listed National Historic Site. It is particularly worth visiting as the largest fortification ever built by the Spanish in the New World, where the first shots of the Spanish-American War were fired. If you're a keen photographer, San Cristobal is a goldmine of panoramic views of the coast, from Old San Juan to Condado and beyond.

Tip:
Guided tours by local rangers visit the extensive tunnel system connecting various sections of the fort. There is an exhibition of military clothing. Be sure to visit the overlook for the Devil's Sentry Box ("Garita del Diablo"), from which, according to legends, soldiers mysteriously disappeared. Tickets to San Cristobal or El Morro can be used to enter either of the forts.

Galería Petrus is a contemporary art gallery located in San Juan, Puerto Rico. The gallery is dedicated to showcasing the works of emerging and established artists from Puerto Rico and around the world, with a particular focus on contemporary art and design.

Founded in 2014, Galería Petrus has quickly become a leading cultural institution in Puerto Rico, known for its dynamic exhibitions and commitment to promoting creative innovation and experimentation. The gallery is located in the vibrant Santurce neighborhood, which is home to a growing community of artists, designers, and other creative professionals.

Galería Petrus features a diverse collection of works, including paintings, sculptures, installations, and other media. The gallery's exhibitions explore a wide range of themes and ideas, from the social and political to the personal and emotional. Through its exhibitions, Galería Petrus aims to challenge and inspire its viewers, inviting them to engage with new and innovative ideas and perspectives.

In addition to its exhibitions, Galería Petrus also hosts a variety of events and programs, including artist talks, workshops, and cultural events. The gallery is a vital center of creative and intellectual exchange in Puerto Rico, and is committed to fostering a dynamic and inclusive cultural community.

The market square was established in 1910 when the area was selected by Puerto Rico's government to build a marketplace. The marketplace building had two levels, the first one for kiosks, food and produce stalls and other service businesses, while the second level had the butcher and the meat market. The building originally also had business spaces, including medical offices.

The market square building has been renovated and modified on numerous occasions throughout the 20th century, and at some point the second level was demolished to increase the area of the main marketplace. The marketplace lost its importance in the later second half of the 20th century which left the area in various stages of disrepair. The building and the neighborhood were revitalized in the 1990s and 2000s when numerous restaurant and entertainment businesses opened.

La Placita historic district is located in and around the historical Santurce Market building. The area is now one of the liveliest social districts in San Juan and it is famous for its nightlife and gastronomy with its numerous restaurants, cafés, bars and dance clubs.