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Alcaldía
One of the highlights of the central plaza is the Alcaldía, which dates from 1789 and has twin turrets resembling those of its counterpart in Madrid. This building houses the office of the mayor of San Juan and is also the site of periodic exhibitions.
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Catedral de San Juan
Although noticeably smaller and more austere than other Spanish churches, the Catedral de San Juan nonetheless retains a simple earthy elegance. Founded originally in the 1520s, the first church on this site was destroyed in a hurricane in 1529. A replacement was constructed in 1540 and, over a period of centuries, it slowly evolved into the Gothic/neoclassical-inspired monument seen today. Most people come to see the marble tomb of Ponce de León and the body of religious martyr St Pio displayed under glass.
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Escuela de Artes Plásticas
The monumental gray-and-white building with a red-roofed rotunda across from El Morro is actually the Escuela de Artes Plásticas. Built as an insane asylum during the 19th century, this grand building looks more like a seat of government with its symmetrical wings, columns, Romanesque arches, porticos, courtyards and fountains. Today it is the source of more than a few jokes by contemporary art students about the mad dreams that continue to take shape within its walls.
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La Fortaleza
A steep climb along Recinto Oeste takes you to the top of the city wall and the guarded iron gates of La Fortaleza . Also known as El Palacio de Santa Catalina, this imposing building is the oldest executive mansion in continuous use in the western hemisphere, dating from 1533. Once the original fortress for the young colony, La Fortaleza eventually yielded its military pre-eminence to the city's newer and larger forts, and was remodeled and expanded to domicile island governors for more than three centuries.
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Paseo de la Princesa
Emanating a rather distinctly European flavor, the Paseo de la Princesa is a 19th-century esplanade situated just outside the city walls. Lined with antique street lamps, shade trees, statues, benches, fruit vendors' carts and street entertainers, this romantic walkway culminates at the magnificent Raíces Fountain, a stunning statue/water feature that depicts the island's eclectic Taíno, African and Spanish heritage.
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Plaza de Armas
Follow Calle San Francisco into the heart of the old city and it opens on to the Plaza de Armas. This is the city's nominal 'central' square, laid out in the 16th century with the classic look of plazas from Madrid and Mexico. In its time, the plaza has served as a military parade ground (hence its name), a vegetable market and a social center.
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Plaza de Colón
Tracing its roots back more than a century to the 400-year anniversary of the first Columbus expedition, the Plaza de Colón lies across the street from the lower part of Fuerte San Cristóbal. The city wall on this end of Old San Juan was torn down in 1897, and the plaza, with its statue of the 'Discoverer' atop a pillar, stands on the site of one of the city's original gated entries, Puerta Santiago.
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Plaza de San José
Adjacent to the uppermost terrace of the Plaza del Quinto Centenario, where it meets Calle San Sebastián, is the Plaza de San José. This relatively small cobblestone plaza is dominated by a statue of Juan Ponce de León, cast from an English cannon captured in the raid of 1797. The plaza is probably the highest point in this city and serves as a threshold to four cultural sites on its perimeter. The neighborhood around the plaza, on San Sebastián and the intersecting Calle del Cristo, is the original home of the restaurant, bar and café scene that began in Old San Juan more than a decade ago.
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Plaza del Quinto Centenario
It's surprising to find such a modern square shoehorned in among all the architectural antiques, but the small Plaza del Quinto Centenario was built in 1992 to honor the 500-year anniversary of Christopher Columbus's first voyage to the Americas.
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Puerta de San Juan
Spanish ships once anchored in the cove just off these ramparts to unload colonists and supplies, all of which entered the city through a tall red portal known as Puerta de San Juan. This tunnel through the wall dates from the 1630s. It marks the end of the Paseo de la Princesa, and stands as one of three remaining gates into the old city (the others lead into the cemetery and the enclave of La Perla). Once there were a total of five gates, and the massive wooden doors were closed each night to thwart intruders.
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