Old San Juan Walking Tour, San Juan

Old San Juan Walking Tour (Self Guided), San Juan

Founded by Spanish colonists in 1509 at a site then known as "Puerto Rico" (Rich Port), San Juan is the third oldest European-established capital in the Americas. In 1521, the words "San Juan" were added to the official name, thus making it "San Juan Bautista de Puerto Rico". This was in keeping with the usual custom of christening the town with both its formal name and that which Christopher Columbus had originally given to the islands, honoring John the Baptist.

Today, this lovely historic area, a UNESCO World Heritage Site since 1983, is characterized by its narrow, blue cobblestone streets, and picturesque, brightly colored buildings, some of which date back almost 500 years. Among them is the La Fortaleza, aka Santa Catalina Palace, the oldest executive mansion still in use on the American continent, built between 1533 and 1540. Added to this, in 1584, was the El Morro castle, designed for San Felipe del Morro. Circumvallation of the city, commenced in 1630, was concluded by 1641. The San Cristóbal fortress, the largest fortification built by the Spanish in the Americas, was completed in 1771.

In the 1890s the United States sought to expand their influence over the Caribbean with the help of a powerful navy. Part of their strategy involved the acquisition of colonies that would serve as strategic points of defense and allow easier passage of ships between the Atlantic and Pacific oceans.

Pursuant to this objective, the United States offered to purchase Puerto Rico and Cuba from Spain for 160 million dollars. After the Spaniards rejected the proposal, the U.S. invaded Puerto Rico, on 25 July 1898, as part of the Spanish–American War. After the Americans prevailed in the war, Spain ceded Puerto Rico in 1899, thus marking the outset of the U.S.-Puerto Rico long-standing relationship.

By the late 1940s, the Old Town of San Juan had fallen into disrepair. To preserve its historic fortifications, the National Historic Site was established in 1949. Among its key landmarks worth checking out are: Plaza Colon (Columbus Square); Paseo de la Princesa (Promenade of the Princess); San Juan Gate and City Walls; Plaza de Armas (Arms Square) with the historic San Juan City Hall; Cathedral of San Juan Bautista; and more.

To explore Old San Juan in detail and to soak in its historical atmosphere, take this self-guided walking tour and feel yourself traveling back in time, if only for an hour or so.
How it works: Download the app "GPSmyCity: Walks in 1K+ Cities" from iTunes App Store or Google Play to your mobile phone or tablet. The app turns your mobile device into a personal tour guide and its built-in GPS navigation functions guide you from one tour stop to next. The app works offline, so no data plan is needed when traveling abroad.

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Old San Juan Walking Tour Map

Guide Name: Old San Juan Walking Tour
Guide Location: Puerto Rico » San Juan (See other walking tours in San Juan)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 10
Tour Duration: 2 Hour(s)
Travel Distance: 3.1 Km or 1.9 Miles
Author: leticia
Sight(s) Featured in This Guide:
  • Plaza Colon (Columbus Square)
  • Castillo San Cristóbal (Fort San Cristobal)
  • Calle de la Fortaleza (Fortaleza Street)
  • Paseo de la Princesa (Princess Promenade)
  • San Juan Gate and City Wall
  • La Fortaleza (The Fortress)
  • Plaza de Armas (Arms Square)
  • Cathedral of San Juan Bautista
  • Museum of the Americas and Cuartel de Ballajá
  • El Castillo San Felipe del Morro (Fort El Morro)
Plaza Colon (Columbus Square)

1) Plaza Colon (Columbus Square)

Columbus Square is one of the most important squares in San Juan. Originally known as Santiago Square, back in the 17th century this square literally marked the doorstep to the old town. Encircled by stone walls in 1635-1641, the only way into the city was then through five gates, the centermost of which was Puerta de Santiago (the Land Gate), straddling the sole 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 had taken the shape of Santiago Square, albeit still unpaved at that time and long afterwards. From 1862, several projects had been undertaken to refurbish the square until in 1870 it finally started to take its current shape. In 1893 the statue of Christopher Columbus was installed to commemorate the 400th anniversary of the discovery of Puerto Rico, upon which the square was renamed Colón, or Columbus Square.

To the south of the square is a gem of Puerto Rican entertainment culture, the Theater Tapia. Inaugurated in 1824, this lovely piece of neoclassical architecture was initially known as the San Juan Municipal Theater. Over 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, the symbol of progress and testament of new and old San Juan!
Castillo San Cristóbal (Fort San Cristobal)

2) Castillo San Cristóbal (Fort San Cristobal) (must see)

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

The fort was named San Cristóbal in celebration of the Spanish victories ejecting English and Dutch interlopers from the island of this 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.

Why You Should Visit:
San Cristóbal is 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.

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 or the "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.

Operation Hours:
Everyday from 9:00 am to 6:00 pm.
Sight description based on Wikipedia.
Calle de la Fortaleza (Fortaleza Street)

3) Calle de la Fortaleza (Fortaleza Street) (must see)

Proudly presiding over the bay of San Juan is the imposing La Fortaleza (Fortress) building, formally known as the Palace of Santa Catalina, the official residence of the Governor of Puerto Rico. The narrow road leading to it, 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 duration is lined with government 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 really stands out above the rest due to the display of umbrellas 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 had colorful kites.
Sight description based on Wikipedia.
Paseo de la Princesa (Princess Promenade)

4) Paseo de la Princesa (Princess Promenade) (must see)

No trip to San Juan is complete without a stroll along the beautiful Princess Promenade. 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.

Princess Promenade is a carefully restored historic landmark, one of the most visited in San Juan, ideal to walk or people watch. It is also a great place to visit for families and children - it is easily accessible and traffic free. There is abundance of trees provides plenty of shade, lots of artisan stalls and street vendors selling local foods, plus festivals and fairs often held here, including artisans fair on weekends.

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

Princess Promenade gets the name from an old 1837 building, located on the promenade, known as La Princesa. Originally, this building served as a municipal prison, although nowadays it houses headquarters of the Puerto Rico Tourism Company and an art gallery.
San Juan Gate and City Wall

5) San Juan Gate and City Wall (must see)

Built in the late 1700s, San Juan Gate is a giant (40 feet) doorway, the last remaining of the original five gates carved into the three-mile wall that once surrounded the city. Presently, 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. This red gate of San Juan played a symbolic role of 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 Catholic liturgy.

The city wall is the most enduring symbol of Puerto Rico, 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 spots, 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 has proved defenseless 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 attempting to recreate the magic mixture of sand, water, and limestone used to stucco the wall. Along with the adjoining fortresses of El Morro and San Cristóbal, the city wall attracts 1.2 million visitors annually.

As you walk through the gate, pause and notice how thick the city walls are. As soon as you pass, look out for street vendors on the corner offering refreshments including Puerto Ricans’ favorite, piragua.
La Fortaleza (The Fortress)

6) La Fortaleza (The Fortress) (must see)

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 walls, was demolished and integrated into the complex, which ensued a new name by which it is currently known, Palacio de Santa Catalina.

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

The fortress underwent a massive reconstruction in 1846 to change its military appearance into a palatial facade. Since then, La Fortaleza has been the residence of 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 in the second floor, and private quarters in the third. It overlooks the high city walls that front the bay, and within the north perimeter of the house are sheltered gardens and a swimming pool.

Why You Should Visit:
A UNESCO-listed World Heritage Site since 1983.
A definite must-see for history and architecture buffs with a taste for Spanish designs.
Sight description based on Wikipedia.
Plaza de Armas (Arms Square)

7) Plaza de Armas (Arms Square) (must see)

Arms Square is one of the main squares in 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 ground for military exercises. Then, by the early 20th century, it was back to Vegetables Square again, and used as a market. Nowadays it is known as Arms Square again.

Arms Square is the city’s de-facto central square, modeled on the classic squares of Madrid and Mexico. Although the square had factually existed for centuries, it was not until 1840 that the city council approved its proper construction, which commenced in 1851. It was then that the four statues made of bronze and oil-coated to simulate marble, representing the Commerce, Industry, Science and the Arts, arrived here. In fact, there were a total of eight statues to be installed, but the other four were lost. In 1872 the original statues were removed and the new marble ones, representing the Four Seasons, put in their place 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 in front of the Palacio de la Real Intendencia on the western side, which houses the Department of State of Puerto Rico.

A highlight on the northern side is the Spanish colonial style Casa Alcaldía – home of San Juan City Hall – built in 1789, with twin turrets resembling those of a sister building in Madrid. A tinkling fountain, seating, shade trees, and a couple of old-school coffee booths make this a good spot for a sightseeing break.

Why You Should Visit:
An important social gathering spot, used for generations, and a popular tourist attraction.

This laid-back space is loved by the locals to buy snacks, watch shows, play dominoes, and chat with friends. Take a seat on a bench to give your feet a break and soak up some of the everyday comings and goings. You can also buy your kids some traditional treats like sesame-seed lollipops or coconut candies.
Cathedral of San Juan Bautista

8) Cathedral of San Juan Bautista (must see)

The Cathedral of San Juan Bautista is the Roman Catholic temple and the seat of the Archdiocese of San Juan de Puerto Rico. This cathedral is one of the oldest buildings in San Juan, and the second oldest cathedral in the Americas (the Cathedral of Santa María la Menor in Santo Domingo, the Dominican Republic, is the oldest). The original cathedral in the then city of Puerto Rico (renamed San Juan after the Spanish-American War) was constructed from wood in 1521. It was destroyed by a hurricane, upon which the current church was built in 1540 to be reshaped several times in the course of the later centuries, with the last remodeling taking place in 1917.

The first school in Puerto Rico (and the oldest school in the United States after Puerto Rico became a territory of the United States) was the Grammar School. The school was established by Bishop Alonso Manso in 1513, in the area where the cathedral would later appear. The school was free and the courses taught here included Latin language, literature, history, science, art, philosophy and theology.

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

Why You Should Visit:
Cathedral of San Juan Bautista is a rare New World example of medieval Spanish architecture. The restored frescoes and the fact that it is still an operational church make it absolutely exceptional. Traditionally, travelers entering San Juan Gate would make this cathedral their first stop in San Juan to thank God for their safe journey.

In this quiet and reverent atmosphere you can almost hear the angels singing. You can walk through it in less than 30 minutes, but you might as well want to take longer and savor the spirituality resonating from the structure.
Sight description based on Wikipedia.
Museum of the Americas and Cuartel de Ballajá

9) Museum of the Americas and Cuartel de Ballajá (must see)

Located in the old Spanish Military Barracks, 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, emphasizing 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, and many more works by artisans from North, South and Central America.

Since its founding, the museum has hosted over 500 temporary exhibitions of art, history and anthropology. The diversity of its exhibition program allows offering a range of creative workshops, conferences, symposiums, musical presentations, among other activities, thus extending the field of impact to the community both inside and outside its headquarters.

Why You Should Visit:
One of the greatest museums in Puerto Rico – gem of curatorial design – offering superb display, from history of colonialism to current Puerto Rico. Cool building, perfect location in Old San Juan, fun and easy to visit.

The main language of the displays is Spanish; some areas offer readable English translations, while others do not. If you do not read Spanish, consider recorded audio tours for rent.
It may take up to one and a half to two hours to tour all the eight galleries. The museum closes at lunchtime, so plan accordingly.

Operation hours:
Tuesday-Friday: 9 am-12 pm/1 pm- 4 pm; Saturday: 12 pm-5 pm; closed on Mondays.
El Castillo San Felipe del Morro (Fort El Morro)

10) El Castillo San Felipe del Morro (Fort El Morro) (must see)

Fort San Felipe del Morro, aka El Morro, is a 16th century citadel on the northwestern-most point of San Juan, named in honor of King Philip II of Spain. It was the second military installation, after La Fortaleza, built on the islet of what is now Old San Juan and Puerta de Tierra.

The construction commenced in 1539, authorized by King Charles V, and was finished in 1790, during which period El Morro had gone from a promontory mounted with a cannon to a six-level fortress designed to guard the entrance to San Juan bay from seaborne invaders. Many more structures were added to the complex over the next 400 years; the outer walls, originally built 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 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 establish as a museum. In 1983, El Morro and the walled-city of Old San Juan were declared UNESCO World Heritage Sites.

Why You Should Visit:
To appreciate the importance of Puerto Rico as a strategic entry point to the Americas and the evolution of El Morro over the last five centuries.

The receipt also allows to visit the Castillo San Cristóbal without having to pay a separate entrance fee (and vice versa).

Operating Hours:
Seven days a week from 9:00 am to 6:00 pm.
Sight description based on Wikipedia.

Walking Tours in San Juan, Puerto Rico

Create Your Own Walk in San Juan

Create Your Own Walk in San Juan

Creating your own self-guided walk in San Juan is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
Old San Juan Squares

Old San Juan Squares

A distinctive feature of Old San Juan is the number of quaint historic squares. Many of them are adorned with beautiful fountains, prominent monuments and intricate sculptures recounting rich history of this amazing city. Check out San Juan’s most popular squares on this self-guided walking tour!

Tour Duration: 1 Hour(s)
Travel Distance: 1.8 Km or 1.1 Miles
Souvenir Shopping

Souvenir Shopping

Puerto Rico was colonized by Spain following the arrival of Christopher Columbus in 1493. Among the crafts that followed the Spanish to the island was mundillo, a kind of decorative lace made of wooden bobbins. Over the next few centuries, the mundillo craft flourished on the island and today is one of the most popular local products sought after by visitors.

Being Caribbean, the country also...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 0.9 Km or 0.6 Miles
San Juan Historical Buildings

San Juan Historical Buildings

San Juan was founded by the Spanish in 1521, which makes it the third oldest European-established capital city on the American continent. Owning to its long history, the old town of San Juan is filled to the brim with heritage colonial buildings.

Chief among them, La Fortaleza is the longest-standing executive mansion in continuous use in America, whereas the Cathedral of San Juan Bautista is...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.4 Km or 1.5 Miles

Useful Travel Guides for Planning Your Trip

13 Distinctively Puerto Rican Goods to Bring Home from San Juan

13 Distinctively Puerto Rican Goods to Bring Home from San Juan

The uniqueness of Puerto Rico is partially associated with its political status - part of the United States yet with a Latin twist. Other than their widely-acknowledged musical talents, e.g. Carlos Santana and Ricky Martin, Puerto Rico is just as rich in many other good things. When you're in...