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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 Col贸n 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.

Plaza de Hostos is a small landscaped square located near Casa Blanca, just in front of Plaza D谩rsena. Dedicated in 1998, the square commemorates the famous Puerto Rican educator, philosopher, intellectual, lawyer, sociologist and independence advocate Eugenio Mar铆a de Hostos, aka 鈥淭he Citizen of the Americas鈥�, whose beautiful statue, featuring de Hostos in the company of joyful kids, created by Jos茅 Buscaglia, stands in the center of the square, watching over the cruise ships entering and leaving the San Juan Bay.

Other than this, guests will find here lots of arts and crafts, as well as traditional pi帽a coladas (a must try!) and other locally-made deserts sold from kiosks dotting the area. A nice place to stop after exploring the southern district of San Juan!

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 Alcald铆a 鈥� 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.

Plaza La Rogativa is the most scenic square in San Juan, offering a 180-degree views of the San Juan Bay. From here, you can also get a clear view of the San Juan Gate and La Fortaleza, much as of the El Yunque national forest in a distance.

The name "Rogativa" means "Procession". According to a legend, during the 1797 attack by the British army, the governor of San Juan ordered a "rogativa" by a group of women, led by the bishop, to march through the city streets at night. Started from the San Juan Cathedral, the procession carried torches and crosses, while singing hymns along the way. The British mistook these sights and sounds for the arrival of Spanish Army reinforcement and gave up the attack. Commemorating that event are the four bronze statues in the center of the square.

Due to its historic significance and scenic beauty, Plaza La Rogativa is also popular a spot for wedding ceremonies. If nothing else, come here in late afternoon to watch the sunset over the San Juan Bay.

Plaza de San Jose, named after the nearby old church, is a small square sitting on the corner of San Sebastian and Cristo Streets. The square center is marked by the statue of Juan Ponce de Leon, the Spanish explorer best known for being the first governor of Puerto Rico during 1508-1509 as well as for his expedition to Florida in 1513. Ponce de Le贸n's finger points to the west, in the direction of his final voyage in search of the Fountain of Youth. The metal for this statue is said to have come from the canons of an English ship destroyed during a failed attack by the British in 1797.

The square is surrounded by historic buildings, such as the San Jos茅 Church and the Pablo Casals Museum. There are multiple cafes and restaurants all around where you can savor excellent Puerto Rican cuisine.

Quincentennial Square is quite modern and was built in 1992 to commemorate the 500th anniversary of Columbus's discovery of the Americas. The centerpiece of the square is a 40-feet tall monument, known as El Totem, designed by Puerto Rican artist Jaime Su谩rez. El Totem is made of clay brought from all over the Americas to signify the origins of the people inhibiting the continent. Down the stairway from El Totem, at the lower end of the square, is a walk-in water fountain.

The square offers an excellent view of the Old San Juan Cemetery where a great number of notable figures in Puerto Rican history have found their final resting place.