San Juan City Hall

The Plaza de Armas of San Juan is one of the main squares in San Juan, the capital of Puerto Rico. It is located on San José Street in Old San Juan, and was designed to serve as the original main square for the city. San Juan City Hall is located to the north of the square, while the Puerto Rico Department of State lies at the west. The square's main feature is a round fountain with four marble statues representing "The Four Seasons", originally placed in the four corners of the square, which had been commissioned in 1856 to the "motherland", to be placed in Paseo La Princesa esplanade in Old San Juan.

Edificio Patio Español (Spanish for 'building of the Spanish courtyard'), also known as La Filarmónica Building, is a mixed-use building located in the Old San Juan historic district of the city of San Juan, Puerto Rico. It was designed in a Spanish Mission Revival-style by civil engineer Eduardo Fossas López and built in 1937 with the purpose of refilling an emptied lot of the old city with a structure that resembled and referenced the Spanish Colonial architecture around it. This emptied lot was formerly the site of a meeting house for a group called Sociedad La Filarmónica ('Society of the Philharmonic'), a scholarly club that was founded by Manuel de Elzaburú and Alejandro Tapia y Rivera with the intention of promoting cultural activities in the city of San Juan. The Patio Español building was added to the National Register of Historic Places in 2005.

The Department of State of Puerto Rico was created in July 1952 and is responsible of promoting the cultural, political, and economical relations between Puerto Rico, other jurisdictions of the United States and foreign countries.

The Catedral Basílica Metropolitana de San Juan Bautista, or in English, Metropolitan Cathedral Basilica of Saint John the Baptist, is the Roman Catholic cathedral of the Archdiocese of San Juan de Puerto Rico. The cathedral is one of the oldest buildings in San Juan, located in Old San Juan, the oldest cathedral in the United States, and is the second oldest cathedral in the Americas. Even though the Cathedral of Santa María la Menor in Santo Domingo in the Dominican Republic, is an older church building, the Cathedral of San Juan Bautista was the first cathedral church in the Americas as San Juan, then known as the city of Puerto Rico, was the first diocese of the New World with bishop Don Alonso Manso in 1511. The site is the location of the first church built in the New World. A private Puerto Rican foundation known as Fundación Protectora de la Catedral Metropolitana de San Juan, Inc. has been established to fund the historical restoration of the building and its art treasures for its 500th anniversary in 2021, and to protect it for coming centuries.

Puerto Rico Ilustrado/El Mundo Building (Spanish: Edificio El Mundo/Puerto Rico Ilustrado) is a historic Art Deco high-rise building located in the Old San Juan historic district of the city of San Juan, Puerto Rico. The building was erected in 1923 to serve as the headquarters of the El Mundo newspaper and the Puerto Rico Ilustrado magazine. The architecture of the building blends numerous styles that represent the conjunction of various artistic movements and architectural schools of the late 19th century and the early 20th century. It is located in a high-rise block that faces the elevated La Palma Bastion portion of the city wall of San Juan which, when observed from beyond, makes the building look taller than it is in reality. The building was added to the National Register of Historic Places in 1997 for its architectural and historic importance.

Santa Ana Church (Spanish: Iglesia de Santa Ana), popularly known as Capilla de Santa Ana, is a historic 17th century Catholic church located in Old San Juan in San Juan, Puerto Rico.This often-missed church is located on Tetuan Street close to the Art Deco-style Banco Popular building. The church, one of the oldest in San Juan, is famous for its pink color, simple yet elegant interior design and its arches. According to historian Maria de los Angeles Castro the church might have been decorated with frescoes created by renown 18th century artist José Campeche. The church is open to visitors and still hosts religious services.

Hotel El Convento is a small hotel in Old San Juan, Puerto Rico, in what was a Carmelite convent, adjoining the San Juan Cathedral square. The cathedral is the second-oldest cathedral in the Western Hemisphere. Hotel El Convento is the oldest member of the Historic Hotels of America. It was also named the premier Small Luxury Hotel in Puerto Rico by the Small Luxury Hotels of the World organization.

Plaza de la Catedral (Spanish for 'cathedral square'), also known as Plazuela de las Monjas ('little square of the nuns'), is a small public square located in front of the Cathedral of San Juan Bautista and next to the former Carmelite convent (now a Hotel El Convento) in the Old San Juan historic district of the city of San Juan, Puerto Rico. The small but historic square is possibly the oldest in the city, dating to the foundation of the cathedral in 1521, and is found at the end of a wide historical residential block bound by the alleyways (Spanish: caletas) of Las Monjas and San Juan to the north and south, respectively, and by Calle del Cristo ('del Cristo Street') to the east. Caleta de San Juan connects this square to the San Juan Gate (Puerta de San Juan), formerly known as the Water Gate (Puerta de Agua) as it was the main harbor entrance into the walled city. This block formerly contained the first Episcopal church in the city between 1909 and 1929 when it was moved to a bigger location in Santurce, and later housed the San Juan Children's Museum (Museo del Niño de San Juan), which closed in 2016.

Capilla del Cristo (Chapel of Christ), also called Capilla del Santo Cristo de la Salud is a small chapel / museum located in the Old San Juan Historic District of Puerto Rico. Built in the 18th century and saved from demolition in the 20th century, the structure has become a cultural icon of Puerto Rico. Most of the articles located at its altar are from 1753. Travel guides list Capilla del Cristo as one of the must-see places of Old San Juan.

The Center for Advanced Studies on Puerto Rico and the Caribbean (Spanish: Centro de Estudios Avanzados de Puerto Rico y El Caribe) is a private institute housed in the former San Ildefonso Conciliar Seminary in Old San Juan, San Juan, Puerto Rico that offers graduate studies in arts and philosophy. It was incorporated on February 28, 1968, by Pablo Casals, Luis Muñoz Marín, Roberto Busó Carrasquillo, and Jaime Benítez. However, it remained inactive and without organization until 1976, when Ricardo Alegría made a request before the Council on Higher Education of Puerto Rico to transform the center into an academic institution. The center is currently accredited by the Middle States Association of Colleges and Schools and it publishes La Revista del Centro de Estudios Avanzados de Puerto Rico y el Caribe.

The Jose V. Toledo Federal Building and United States Courthouse is a historic post office and courthouse located at Old San Juan, Puerto Rico. It is a courthouse for the United States District Court for the District of Puerto Rico. It is also the site for oral argument before the United States Court of Appeals for the First Circuit, when that court sits in Puerto Rico.

Catedral, located within Old San Juan, is one of 7 subbarrios of San Juan Antiguo barrio in the municipality of San Juan in Puerto Rico.