San Juan, Puerto Rico

Juan Ponce de León founded San Juan in 1508, five years before discovering Florida. The Spanish Empire ruled the Isleta de San Juan for nearly 400 years before Puerto Rico became a U.S. territory. Over 500 years later, it is your turn to discover San Juan. Use this travel guide so you do not miss any of the amazing places to see in this capital city.

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Welcome to San Juan, Puerto Rico - Encircle Photos

1 Welcome to San Juan, Puerto Rico

Welcome to La Ciudad Amurallada (walled city), better known as San Juan, Puerto Rico. The capital city of the U.S. territory in the heart of the Caribbean has everything you want for a perfect vacation. The highlights include golden sunshine on golden beaches to over 500 years of history. Enjoy exploring Old San Juan, the Capital District and the oceanfront resort and entertainment community at Condado. You will be so busy you will need another vacation when you get home.

Bastión de Las Palmas de San José, 100 Calle de Tetuan, San Juan, 00901, Puerto Rico
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Paseo de la Princesa in San Juan, Puerto Rico - Encircle Photos

2 Paseo de la Princesa in San Juan, Puerto Rico

At the base of the city wall at the southwest corner of Old San Juan is a delightful promenade called Paseo de la Princesa. The short, tree-lined esplanade ends at the Bay of San Juan. Along the way you will encounter artisan stalls and street vendors. On weekends and holidays, the lively ambiance is filled with music and street food. Princess Walk was created in 1853. At the start is this section of wall known as the Bastion of the Right of San Justo and Pastor. It was named after a medieval basilica in Barcelona. This fortification served as a critical defense along the waterfront. The sentry box dates from the late 18th century.

Bastión de la Derecha de San Justo y Pastor, Paseo de la Princesa, San Juan, 00901, Puerto Rico
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Plaza of the Heritage of Americas in San Juan, Puerto Rico - Encircle Photos

3 Plaza of the Heritage of Americas in San Juan, Puerto Rico

There are five intriguing sculptures in the Plaza of the Heritage of Americas created by José Buscaglia. Two are in the gardens flanking a central double staircase acting as a platform for three additional allegories. They represent the core influences of American heritage: faith, liberty, blood, Hispanic origin and cultural values. These 8.5 foot bronze statues are called Herencia Social meaning Hispanic Heritage. It shows the Lady of Elche offering her son to the New World. Judging from her elaborate headdress, Dama de Elche is believed to be an Iberian princess. The original artifact was created in the 4th century BC and discovered in Spain in 1897.

La Fuente de la Herencia de las Américas, Paseo de la Princesa, San Juan, 00901, Puerto Rico
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La Princesa in San Juan, Puerto Rico - Encircle Photos

4 La Princesa in San Juan, Puerto Rico

La Princesa was a former prison. The initial city jail was built in 1837 and then expanded in 1854. It incarcerated up to 240 inmates until 1965. After an extensive renovation, the building was converted into the headquarters of Puerto Rico’s Tourism Company. This landmark also hosts a contemporary art exhibit.

2 Paseo de la Princesa, San Juan, 00901, Puerto Rico
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Raíces Fountain in San Juan, Puerto Rico - Encircle Photos

5 Raíces Fountain in San Juan, Puerto Rico

The terminus of Paseo de la Princesa is accented with the exquisite Raíces Fountain. Raíces means roots. The sculptural group represents the mix of cultures that shaped Puerto Rico, predominately the Spaniards, Africans and the indigenous Taino people. The ensemble was designed by Miguel A. Carlo and created by Luis Sanguino. The installation in 1992 was part of celebrating the 500th anniversary of the discovery of the Americas.

Raíces Fountain, 101 Paseo de la Princesa, San Juan, 00901, Puerto Rico
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Paseo del Morro in San Juan, Puerto Rico - Encircle Photos

6 Paseo del Morro in San Juan, Puerto Rico

The end of Paseo de la Princesa marks the transition to Paseo del Morro. This National Recreation Trail begins below La Fortaleza. The mid-16th century fortress still serves as the executive mansion for the governor of Puerto Rico. The walking path follows the bay at the base of the city walls. These three miles of masonry are called La Muralla. Some sections measure 20 feet thick and 40 feet tall. The defenses were constructed from 1634 until 1782. This sentry post is next to the San Juan Gate. La Puerta de San Juan was built in 1634, making it the oldest of the original five gates (puertas) into Old San Juan. It was also the formal entrance. Countless Spanish dignitaries arrived here starting in 1540.

Puerta De San Juan, Paseo del Morro, San Juan, 00901, Puerto Rico
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Bastion along Paseo del Morro in San Juan, Puerto Rico - Encircle Photos

7 Bastion along Paseo del Morro in San Juan, Puerto Rico

After visiting some of the landmarks just inside of the San Juan Gate, continue your leisurely stroll along Paseo del Morro. The walkway extends to Castillo San Felipe del Morro San Juan, the number one attraction in Old San Juan. Along the way you can continue to admire the features of the impressive city walls. This is Bastión de San Agustín. The outward projection of the curtain wall allowed soldiers to defend the flanks with heavy artillery during an attack from the sea.

Paseo del Morro, San Juan, 00901, Puerto Rico
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El Convento in San Juan, Puerto Rico - Encircle Photos

8 El Convento in San Juan, Puerto Rico

El Convento was founded in the mid-17th century for nuns in the Order of the Blessed Virgin Mary of Mount Carmel. The initial Carmelite sisters arrived from Santo Domingo in the Dominican Republic. The first building was replaced with the current one two hundred years later. This canary-yellow façade was the entrance to the monastery’s chapel. The property closed in 1903 and then reopened in 1962 as a boutique hotel. After another extensive renovation about thirty years later, it became the Hotel El Convento.

100 Calle del Cristo, San Juan, 00901, Puerto Rico
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Dome above Nave in San Juan Cathedral in San Juan, Puerto Rico - Encircle Photos

9 Dome above Nave in San Juan Cathedral in San Juan, Puerto Rico

The first Roman Catholic church in San Juan was built in 1521. After being destroyed by a hurricane, it was replaced by this Neoclassical structure in 1540. It was called Cathedral of San Juan Bautista after the name of the settlement at that time. Now it is formally called the Metropolitan Cathedral Basilica of Saint John the Baptist. It is the oldest cathedral in the United States. This impressive dome crowns the nave constructed of elegant white marble.

151 Calle del Cristo, San Juan, 00902, Puerto Rico
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Juan Ponce de León Tomb in San Juan Cathedral in San Juan, Puerto Rico - Encircle Photos

10 Juan Ponce de León Tomb in San Juan Cathedral in San Juan, Puerto Rico

Juan Ponce de León was a Spanish conquistador. His first visit to the New World was aboard Christopher Columbus’s second voyage in 1493. After securing Hispaniola for Spain, he created a settlement in San Juan in 1508 and became the first governor of Puerto Rico a year later. He was also the first European explorer to land at La Florida and travel along the eastern coast of today’s United States. In 1521, at the age of 47, Ponce de León suffered wounds during a battle with the Calusa, an indigenous tribe in southwest Florida. He died in Havana and was interred at the Church of San José in San Juan. In 1912, his body was moved to the Metropolitan Cathedral Basilica of Saint John the Baptist.

151 Calle del Cristo, San Juan, 00902, Puerto Rico
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Courtyard of Seminario Conciliar in San Juan, Puerto Rico - Encircle Photos

11 Courtyard of Seminario Conciliar in San Juan, Puerto Rico

This Catholic seminary was founded in 1832 with the mission to educate young men as priests. The Seminario Conciliar de San Ildefonso evolved into a prestigious school for physics and chemistry. Then additional departments were added including literature, mathematics and geometry. After the school moved in 1948, the building was a convent until it closed in 1972. After an extensive renovation, Seminario Conciliar reopened in 1986 as the Center for Advanced Studies of Puerto Rico and the Caribbean.

52 Calle del Cristo, San Juan, 00901, Puerto Rico
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San José Church in San Juan, Puerto Rico - Encircle Photos

12 San José Church in San Juan, Puerto Rico

Iglesia San José was the first church in the New World. Dominican Order friars began building it in 1532. The Catalan structure evolved for the next two hundred years. In Plaza de San José is a statue of Juan Ponce de León. The Spanish explorer had strong ties to Iglesia San José. While the first governor of Puerto Rico, he donated the land for the construction. When he died in 1521, he was initially buried in Havana. Then his body was interred in San José Church from 1559 until 1836 when it was transferred to the Cathedral of San Juan Bautisa. The 15 foot statue of the conquistador was created in 1882 using British cannons captured during their attack on San Juan in 1797.

Plaza San José, Calle San Sebastián, San Juan, 00901, Puerto Rico
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Telúrico Totem in San Juan, Puerto Rico - Encircle Photos

13 Telúrico Totem in San Juan, Puerto Rico

In 1492, Christopher Columbus discovered three islands in the New World: San Salvador, Cuba and Hispaniola (currently Haiti and the Dominican Republic). To celebrate the 500th anniversary, local sculptor Jaime Suárez was commissioned to create the Telúrico Totem. The 39 foot sculpture is crafted with ceramics and granite from across the Americas. The column seems taller because of its position at the top of a staircase. The monument and several water fountains are the centerpieces of Quincentennial Plaza.

Tótem Telúrico, Plaza del Quinto Centenario, Calle del Cristo, San Juan, 00926, Puerto Rico
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Museum of the Americas in San Juan, Puerto Rico - Encircle Photos

14 Museum of the Americas in San Juan, Puerto Rico

The foundation of Puerto Rico was influenced by the Spanish, Africans and Taíno, the Pre-Columbian indigenous people. Each had a profound impact on shaping Puerto Rico, the Caribbean and parts of North, Central and South America. The Museum of the Americas dramatically tells their stories. The exhibits explain their art, history and culture. The Museo de Las Americas’ building is also historical. The Ballajá Barracks was built by the Spanish in the mid-19th century. The 83,000 square feet of space accommodated hundreds of soldiers and their families until 1898. Then it housed a U.S. infantry until 1939 when it became a military hospital during World War II.

Museo de las Américas, Calle Beneficencia, San Juan, 00926, Puerto Rico
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Orientation to El Morro in San Juan, Puerto Rico - Encircle Photos

15 Orientation to El Morro in San Juan, Puerto Rico

Castillo San Felipe del Morro is the uncontested highlight of Old San Juan. Before starting your exploration of this San Juan National Historic Site, become familiar with the surrounding landmarks. In the upper left corner is the lighthouse in the middle of El Morro, the old Spanish fort. Side-by-side on the hill are the San Antonio Bastion Guardhouse (1897) on the left and the Powder Magazine (1783) on the right. The middle masonry wall is San Antonio Bastion (1783) and the nearest crenelated wall is Santa Rosa Bastion (1783). The pink dome between them is the Cemetery Chapel (1862). In the foreground is Santa Maria Magdalena de Pazzis Cemetery (1814).

Calle Tiburcio Reyes, San Juan, 00901, Puerto Rico
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Overview of El Morro in San Juan, Puerto Rico - Encircle Photos

16 Overview of El Morro in San Juan, Puerto Rico

You are about to be one of the two million people a year who visit Castillo San Felipe del Morro. This massive, six-level fortress dominates 70 acres at the northwest tip of Isleta de San Juan. El Morro was a formidable military post for 422 years, beginning with the Spanish in 1539 and ending with the U.S. Army in 1961. This must-see citadel was designated as a UNESCO World heritage Site in 1983.

El Morro, Calle del Morro, San Juan, 00901, Puerto Rico
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History of El Morrow in San Juan, Puerto Rico - Encircle Photos

17 History of El Morrow in San Juan, Puerto Rico

After walking across a large, treeless hill called the Field of Fire, over a drawbridge and beneath a Spanish coat of arms, you step into nearly five hundred years of history. In 1539, King Charles I of Spain ordered the construction of a defense for Puerto Rico de San Juan Bautista. The initial fort was small and ill-equipped. In 1587, his son, Philip II of Spain, commissioned Battista Antonelli to design an elaborate expansion. Antonelli was the chief architect of Spanish forts throughout the New World. The citadel was named Castillo San Felipe del Morro in honor of the king. In English, it means the Castle of Saint Philip on the Headland. Additional enhancements were made under King Felipe IV in the mid-17th century and King Charles III one hundred years later. By the late 1780s, El Morro was called a Defense of the First Order and was one of the best fortifications in the Americas. It proved worthy of these accolades several times. El Morro was attacked by the buccaneer Sir Frances Drake in 1595, by George Clifford, 3rd Earl of Cumberland, three years later, the Dutch in 1625, the British in 1797 and the American Navy in 1898. In 1915, the first shot by the United States in World War I was fired from El Morro on a German ship. It was also a U.S. military post during WWII. After the U.S. Army moved out in 1961, El Morro was turned over to the U.S. National Park Service.

El Morro, Calle del Morro, San Juan, 00901, Puerto Rico
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Isla de Cabras from El Morro in San Juan, Puerto Rico - Encircle Photos

18 Isla de Cabras from El Morro in San Juan, Puerto Rico

From the top of Castillo San Felipe del Morro you get an excellent view of Isla de Cabras. Goats Island in English. The Spanish took advantage of its strategic position on the other side of San Juan Bay by building Fortín San Juan de la Cruz (Fort Saint John of the Cross) in the mid-17th century. These two forts could effectively crossfire against approaching enemy ships. More commonly called El Cañuelo, the small historic citadel is a UNESCO World Heritage Site. Unfortunately, it is closed to visitors. The island also served as a leper colony. The area is now the Isla de Cabras Recreational Park. This is a great place for a scenic jog, stroll or picnic.

El Morro, Calle del Morro, San Juan, 00901, Puerto Rico
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Lighthouse at El Morro in San Juan, Puerto Rico - Encircle Photos

19 Lighthouse at El Morro in San Juan, Puerto Rico

Puerto Rico’s first lighthouse was constructed at Castillo San Felipe del Morro in 1846. The beacon at the mouth of San Juan Bay was replaced twice before the U.S. Coast Guard built the current version in 1908 using a Moorish Revival design. The square, crenellated tower only stands 51 feet. Yet its position on the sixth level of El Morro adds 140 feet of height. Fans of lighthouses will be pleased to learn there are ten more active faros on the island.

El Morro, Calle del Morro, San Juan, 00901, Puerto Rico
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Sentry Box on Curtain Wall at El Morro in San Juan, Puerto Rico - Encircle Photos

20 Sentry Box on Curtain Wall at El Morro in San Juan, Puerto Rico

To fully appreciate the magnitude of Castillo San Felipe del Morro, stand next to it and look up. The masonry averages 18 feet thick. The curtain walls reach a height of 60 feet. And at every corner is a sentry box (garita) where armed soldiers watched for approaching intruders. Now breathe deep and be thankful you do not have orders to attack this impenetrable defense.

El Morro, Calle del Morro, San Juan, 00901, Puerto Rico
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Albizu University in San Juan, Puerto Rico - Encircle Photos

21 Albizu University in San Juan, Puerto Rico

Dr. Carlos Albizu-Miranda founded the Puerto Rico Institute of Psychology in 1966. The initial curriculum was focused on clinical psychology at the graduate level. A second campus opened in Miami in 2000. Now named Albizu University, its expanded mission is on broad mental health issues in multicultural communities. CAU has an enrollment of about 2,000 students.

Universidad Carlos Albizu, 151 Calle Tanca, San Juan, 00901, Puerto Rico
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Castillo San Cristóbal in San Juan, Puerto Rico - Encircle Photos

22 Castillo San Cristóbal in San Juan, Puerto Rico

During the 16th through the 18th centuries, the Spanish built countless fortresses in the Caribbean and South America. The largest was Castillo San Cristóbal (Saint Christopher Fort). This formidable defense spanned 27 acres of Old San Juan. Fort San Cristóbal was constructed from 1765 until 1783, a remarkably short time for such a huge undertaking. The citadel engaged in battle twice. The first was in 1797 when a British onslaught was repelled. The second was 101 years later when their cannons fired against the USS Yale. This ill-fated move engaged Puerto Rico into the Spanish-American War. Before the end of the year, Spain ceded Puerto Rico to the United States in the Treaty of Paris. Notice the three flags. They represent the United States, Puerto Rico and the Spanish Empire. Do not miss visiting this San Juan National Historic Site. The fort is also designated a UNESCO World Heritage Site.

Castillo San Cristóbal, 501 Calle Norzagaray, San Juan, 00901, Puerto Rico
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Christopher Columbus Monument in San Juan, Puerto Rico - Encircle Photos

23 Christopher Columbus Monument in San Juan, Puerto Rico

Three ships sailed under the command of Christopher Columbus during his first voyage from August of 1492 until March of 1493. Six months later, a fleet of 17 ships accompanied him at the start of his second voyage. During his exploration of several Caribbean islands, he landed in Puerto Rico on November 19, 1493. The natives called it Borinquen. Columbus renamed it San Juan Bautista in honor of Saint John the Baptist. This marble column and statue in Plaza de Colon pays tribute to the 400th anniversary of the discovery. Surrounding the monument are 16 bronze reliefs showing major events of Columbus’ expedition.

Plaza Colón, Calle Fortaleza, San Juan, 00901, Puerto Rico
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Antiguo Casino de Puerto Rico in San Juan, Puerto Rico - Encircle Photos

24 Antiguo Casino de Puerto Rico in San Juan, Puerto Rico

The Christopher Columbus Monument at Plaza Colón marks the border of Old San Juan. As you continue your walking tour headed west, you enter the Capital District in the Puerta de Tierra sector. The first structure to admire has an elegant French Beaux Arts façade yet a misleading name. The Old San Juan Casino is not a casino. It was a club for the social elite when it opened in 1917. The property was later repurposed as an officers’ club, a music school and finally the Institute of Puerto Rican Culture. Today, Antiguo Casino de Puerto Rico is a special event venue for weddings and company meetings. It is listed on the National Register of Historic Places.

Antiguo Casino, Ponce de León Ave and Norzagaray, San Juan, 00901, Puerto Rico
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Casa Olímpica in San Juan, Puerto Rico - Encircle Photos

25 Casa Olímpica in San Juan, Puerto Rico

This Neoclassical architecture with Ionic columns supporting the portico belies its origin. This opened in 1913 as the first YMCA in Puerto Rico. In 1992, when it became the headquarters for the Puerto Rico Olympic Committee, it was renamed Casa Olímpica. Olympic House doubles as a romantic location for weddings.

Casa Olímpica, Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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Puerto Rican Athenaeum in San Juan, Puerto Rico - Encircle Photos

26 Puerto Rican Athenaeum in San Juan, Puerto Rico

The Ateneo Puertorriqueño was established in 1876 as a cultural institution. Their mission is to advance science, literature and fine arts. The Puerto Rican Athenaeum still lives that mission by offering a museum and library. It also sponsors programs for the performing arts. This impressive structure in the Capital District opened in 1932 based on the drawings of Franciso Roldán. The building displays several features of Moorish design called Mudéjar. These include a colonnade of horseshoe arches. The patterned ceramic mosaic over the entrance is called a zellige.

Ateneo Puertorriqueño, Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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Carnegie Library in San Juan, Puerto Rico - Encircle Photos

27 Carnegie Library in San Juan, Puerto Rico

Andrew Carnegie became extremely rich as the founder of a steel company that bore his name. He then gave away 90% of his fortune as a philanthropist. Part of his legacy was helping to fund 2,500 public libraries. The Carnegie Library on Avenida Juan Ponce de León was established in 1916. It absorbed the collection of books from the Island Library. This Neoclassical building was created by architect Ramón Carbia. The library closed in 1965. Three decades passed before the structure was extensively remodeled and reopened.

Carnegie Library, 7 Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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Casa de España in San Juan, Puerto Rico - Encircle Photos

28 Casa de España in San Juan, Puerto Rico

Casa de España was found in 1914 as an exclusive social club for people living in San Juan of Spanish descent. This structure opened in 1935 based on a design by Pedro de Castro y Besosa. This prolific architect is credited with nearly 200 homes, apartments and civil buildings in San Juan during the early 20th century. The architecture reflects a Moorish Revival style found in major landmarks in Andalusia, Spain, especially in Granada and Córdoba. The House of Spain is now available for private events.

Casa de España, 9 Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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Monuments in Capital District of San Juan, Puerto Rico - Encircle Photos

29 Monuments in Capital District of San Juan, Puerto Rico

There are 11 plazas in the Capital District of Puerta de Tierra. They are all graced by one or more sculptures. For example, Plaza en Honor a Los Presidents has statues of all the U. S. presidents who visited Puerto Rico. Other monuments are tributes to Puerto Rican governors, leaders and artists plus fallen police officers and soldiers killed in battle. This ensemble is at Plaza en Honor a Los Maestros Puertorriqueños. The translation is the Plaza in Honor of Puerto Rican Teachers. Around the amphitheater are biographies of outstanding educators. Next to it is a plaza devoted to accomplished Puerto Rican women.

Monumento Al Maestro Puertorriqueño, Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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Capitol Building in San Juan, Puerto Rico - Encircle Photos

30 Capitol Building in San Juan, Puerto Rico

The Foraker Act established Puerto Rico’s government in 1900. It was headed by a governor initially appointed by the U.S. president and governed by a bicameral legislative body. The capital city was designated as San Juan. In 1917, the residents of Puerto Rico were granted U.S. citizenship. In 1952, the Constitution of the Commonwealth of Puerto Rico was passed. This made Puerto Rico a commonwealth of the United States. The Capitol Building was built in 1929. Its Classic Revival design with a white marble façade and dome was created by architect Rafael Carmoega. The building is often called the Palacio de las Leyes (Palace of Laws) because it serves as the chambers for the Senate and House of Representatives. El Capitolio de Puerto Rico anchors the center of the Capital District in Puerta de Tierra.

El Capitolio, 1 Democracy Square, San Juan, 00902, Puerto Rico
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Holocaust Memorial in San Juan, Puerto Rico - Encircle Photos

31 Holocaust Memorial in San Juan, Puerto Rico

Across Constitution Avenue from the Capitol of Puerto Rico is the Holocaust Memorial. The monument consists of a large sheet of curved steel with symbolic flames on top. In the center are the carved-out silhouettes of a family standing hand-in-hand titled the “Shadow of Absence.” There are also plaques describing the horror against Jews during World War II. The memorial was created in 2012 by husband and wife Michael Berkowicz and Bonnie Srolovitz.

Holocaust Memorial, Constitution Avenue, San Juan, 00907, Puerto Rico
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School of Tropical Medicine in San Juan, Puerto Rico - Encircle Photos

32 School of Tropical Medicine in San Juan, Puerto Rico

The School of Tropical Medicine was established in 1926 as a research institute for learning the causes of anemia and how to treat it. This condition is characterized by a low number of red blood cells resulting in inadequate oxygenation of the body. In Puerto Rico, a significant percent of the population suffered from the malady because of hookworm. The school’s founder, Bailey K. Ashford, helped cure over 300,000 residents. The institute also addressed other diseases common in the tropics. In 1949, Escuela de Medicina Tropical was merged with the School of Medicine of the University of Puerto Rico. The building by architect Rafael Carmoega is listed in the National Register of Historic Places.

Edificio Antigua Escuela de Medicina Tropical, Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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Santiago Iglesias Pantin Monument in San Juan, Puerto Rico - Encircle Photos

33 Santiago Iglesias Pantin Monument in San Juan, Puerto Rico

This tribute to Santiago Iglesias Pantin is an example of the statues of successful politicians and leaders you will find in the Capital District. Santiago Iglesias was born in Spain in 1872 and arrived in Cuba as a stowaway. His long list of accomplishments included being a labor leader, journalist, founder of the country’s Socialist Party, Puerto Rico Senator for 16 years, and member of the U.S. Congress for six years.

Statue of Santiago Iglesias Pantin, Paseo Covadonga, San Juan, 00901, Puerto Rico
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Seahorse Sculpture in San Juan, Puerto Rico - Encircle Photos

34 Seahorse Sculpture in San Juan, Puerto Rico

A few hundred feet east of the main cruise terminal is this seahorse statue. The steel and bronze sculpture stands an impressive 38 feet. The graceful outdoor art was created by José Ignacio Morales. His nickname is El Artístico. For four decades, this blacksmith by trade has converted pieces of junk metal into stunning artwork across the Caribbean.

Seahorse Statue, Muelle 6, San Juan, 00901, Puerto Rico
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Evolution of Ships in San Juan, Puerto Rico - Encircle Photos

35 Evolution of Ships in San Juan, Puerto Rico

Ocean vessels have sailed to Puerto Rico since Christopher Columbus discovered the island in 1493. These two ships docked at the San Juan Cruise Port Terminal represent the evolution over hundreds of years. On the right is El Galeón. This is a 2009 replica of the type of tall ships that traveled between Spain and the New World during the 16th and 17th centuries. The 170 foot, wooden galleon has seven sails on three masts. On the left is the Carnival Magic. The 1,845 passenger ship was christened in 2011. San Juan enjoyed a robust cruise industry until it was disrupted by Hurricane Maria in 2017. Fortunately, the city has again become a popular port of call with an estimated 1.7 million passengers arriving each year.

Muelle 4, Calle Marina, San Juan, 00901, Puerto Rico
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Plaza de la Dársena in San Juan, Puerto Rico - Encircle Photos

36 Plaza de la Dársena in San Juan, Puerto Rico

Many of the squares in Old San Juan get crowded with tourists, especially when several cruise ships are in port. A relaxing alternative is Plaza de la Dársena. This small, waterfront park is located at the west end of the piers in San Juan Bay. The shaded benches are an ideal place to watch the comings and goings of ships and ferries. The plaza also features a gazebo to escape the sun, a water fountain and cool breezes off the water. On weekends, the square hosts a popular crafts market.

Dársenas Square, Calle Comercio, San Juan, 00901, Puerto Rico
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La Casita de Rones in San Juan, Puerto Rico - Encircle Photos

37 La Casita de Rones in San Juan, Puerto Rico

The Department of Agriculture and Commerce built La Casita in 1937. The heritage building in Plaza de la Dársena is now a highly-rated yet moderately-priced restaurant and bar. The specialty drinks at La Casita de Rones feature Puerto Rican rum. There is also a rum tasting area plus a shop selling … you guessed it … rums from around the island.

La Casita de Rones, Dársenas Square, Calle Comercio, San Juan, 00901, Puerto Rico
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U.S. Customs House in San Juan, Puerto Rico - Encircle Photos

38 U.S. Customs House in San Juan, Puerto Rico

Anchoring the western side of Plaza de la Dársena is the U.S. Customs House. The two-level, pink and white concrete structure would be unremarkable if not for the plateresque ornamentation in the center. Imbedded among the terracotta are grotesques and lions, an eagle, coat of arms, clam shell designs above the windows and entrance plus green decorative motifs. Aduana de San Juan was created by architect Albert B. Nichols and built in 1924. It is listed with the National Register of Historic Places.

1 Calle La Puntilla, San Juan, 00901, Puerto Rico
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Home of Our Lady of Providence in San Juan, Puerto Rico - Encircle Photos

39 Home of Our Lady of Providence in San Juan, Puerto Rico

In 1892, Sister Ignacia de Santa Eulalia had a dream to build a nursing facility to care for the homeless elderly. The humble hospital and nursing home she founded was replaced in 1913 with this gorgeous structure by architect José Lázaro Costa. The Home of Our Lady of Providence was expanded in 1991. Hogar Nuestra Señora de la Providencia is located in the Puerta de Tierra neighborhood.

Home Our Lady of Providence, 207 Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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San Agustín Parish Church in San Juan, Puerto Rico - Encircle Photos

40 San Agustín Parish Church in San Juan, Puerto Rico

Most of the early residents of Isleta de San Juan lived within the protective walls of Old San Juan. When it became too crowded, people began moving to the surrounding areas such as today’s Puerta de Tierra neighborhood. To serve their religious needs, the brothers from the Redemptorist Order built a Roman Catholic church on this site in 1886. By 1915, this replacement church was constructed, along with a convent and school. The Neo-Gothic, concrete façade of San Agustín Parish Church features a rose window flanked by two asymmetrical bell towers.

265 Avenida Juan Ponce de León, San Juan, 00901, Puerto Rico
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Isleta de San Juan, Puerto Rico - Encircle Photos

41 Isleta de San Juan, Puerto Rico

San Juan is a fairly large city. More than 400,000 people live within the 77 square mile municipality. Yet the two areas of greatest interest to tourists – Old San Juan and the Puerta de Tierra neighborhood – are huddled together on the Isleta de San Juan. This three square mile island is shaped by the Atlantic Ocean in the north and the Bay of San Juan to the south. These Historic and Capital Districts are connected to the mainland by three bridges near Condado.

Playa El Escambrón, Calle San Augustín, San Juan, 00901, Puerto Rico
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Fortín de San Gerónimo in San Juan, Puerto Rico - Encircle Photos

42 Fortín de San Gerónimo in San Juan, Puerto Rico

Visitors explore the walls and forts encircling Old San Juan but are often oblivious to other fortifications built by the Spaniards. In 1609, El Boquerón was constructed at the east end of the islet near the mouth of today’s Condado Lagoon. The four cannon defense battery was destroyed by privateers in the late 16th century. When the half-acre fortress was rebuilt, it was named Fortin de San Gerónimo de Boquerón. In 1797, San Gerónimo and the adjacent Fort of San Antonio were relentlessly bombarded by the British. Despite being grossly outnumbered and suffering crippling damage to their fort, the defenders repelled the attack. The citadel was rebuilt a couple years later and became a military post. This National Register of Historic Places property is now attached to the Caribe Hilton Hotel. Unfortunately, the historic site is closed because of its dilapidated condition.

1 Calle San Gerónimo, San Juan, 00907, Puerto Rico
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Condado in San Juan, Puerto Rico - Encircle Photos

43 Condado in San Juan, Puerto Rico

In Spanish, the word Condado means country. It feels like you have entered a different country when you contrast Old San Juan – with its historic structures and blue cobblestone streets –with the high-rises in this oceanfront community. Condado began in the early 20th century as suburban sprawl from Old San Juan. Soon, wealthy Americans such as the Vanderbilts built lavish second homes in the area. This was followed with a development boom of hotels and resorts. By the end of the century, large condominiums were added along the Atlantic Ocean beach and Condado Lagoon. Simultaneously, the number of restaurants, bars, shops, museums and entertainment venues grew exponentially. Today, most tourists come to see Old San Juan but spend most of their vacation in Condado.

Ashford Ave. & PR-1, San Juan, 00907, Puerto Rico
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San Juan, Puerto Rico Composite of Two Photos - Encircle Photos

San Juan, Puerto Rico Composite of Two Photos

Two photos of San Juan, Puerto Rico are: the skyline of Condado along Laguna del Condado, and a sentry post or garita at Castillo San Cristóbal (Saint Christopher Fort), the largest Spanish fortress in the Caribbean.

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