San Juan is anything but uncool. Puerto Rico’s capital city elegantly plants its Spanish heritage all over the place.

From the cobblestone streets of Old San Juan to the large concentration of art galleries and museum, San Juan is that kid in school with the fancy backpack.

This city does have it all, but that doesn’t mean it is too cool for visitors. Spend some time in these plazas, the squares of San Juan, and you too can be both cool and square in Puerto Rico.

Now that we've convinced you that it's hip to be square, the only thing left to do is find cheap flights to San Juan. 

Plaza del Quinto Centenaria: The modern square in town is the Plaza del Quinto Centenaria. This plaza was built for the 1992-1993 celebrations of the 500th anniversary of the New World. Aside from fountains, columns, and steps telling of San Juan’s 500 year heritage, Plaza del Quinto Centenaria also afford views over El Morro and the Atlantic Ocean.

Plaza de Las Armas: Right in the heart of Old San Juan, you will have a hard time avoiding this central square. Plaza de Las Armas hints at the classic plazas of Spain. The square houses the San Juan City Hall, built in 1789 to look like Madrid’s version. Plaza de Las Armas is a popular place to stroll in the evening, amidst large tress, colonial architecture and even an old fashioned coffee booth or two.

Plazuela de La Rogativa: This plaza may be small, but its legends are large. Perhaps one of San Juan’s greatest tales, Plazuela de La Rogativa takes it name from the statue La Rogativa, meaning The Procession. The sculpture shows the procession of faithful Catholics and their bishop. As legend would have it, supposedly the sculpture represents a procession that took place in 1797. British forces invading Puerto Rico turned their boats around once they saw figures they believed to be Spanish reinforcements. Those figures are thought to be a procession of the faithful. Aside from San Juan legend, Plazuela de La Rogativa boasts views of La Fortaleza and the city wall.

Plaza de Colón: Columbus may not have discovered inhabited Puerto Rico, but Plaza de Colón commemorates the importance of his stop here in Plaza de Colón. Across the street from Fuerte San Cristóbal and at the main entrance to Old San Juan, you can expect this square to be busy with people and traffic. Within the plaza is a statue of Columbus, up high on a pedestal. The statue marks the spot of one of the city’s original gated entries, Puerto Santiago.

Paseo de la Princesa: While this promenade may be more rectangle than square, it is one of San Juan’s most beautiful open stretches. The wide bayside promenade stretches along the bay, just beneath the Old City’s Spanish colonial walls. The highlight along this walk is the Raíces Fountain, especially for those at night. The fountain is made up of the Adonises and Amazon warrior goddesses riding huge horses and fish. It was intended to celebrate Puerto Rico’s Taíno, Spanish and African heritage. Just don’t get too close. This fountain is more shower than showpiece.

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