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San Juan Gate, Calle San Francisco and Calle Recinto Oeste, built around 1635, just north of La Fortaleza, several blocks downhill from the cathedral, was the main point of entry into San Juan, if you arrived by ship in the 17th and 18th centuries. The gate is the only one remaining of the several that once pierced the fortifications of the old walled city. For centuries it was closed at sundown to cut off access to the historic Old Town. (Bus: Old City Trolley.)

Plazuela de la Rogativa, Caleta de las Monjas, is a little plaza with a statue of a bishop and three women, commemorating one of Puerto Rico's most famous legends. In 1797, from across San Juan Bay at Santurce, the British held Old Town under siege. That same year they mysteriously sailed away. Later, the commander claimed he feared that the enemy was well prepared behind those walls; he apparently saw many lights and believed them to be reinforcements. Some people believe that those lights were torches carried by women in a rogativa, or religious procession, as they followed their bishop. (Bus: Old City Trolley.)

The city walls around San Juan were built in 1630 to protect the town against both European invaders and Caribbean pirates. The city walls that remain today were once part of one of the most impregnable fortresses in the New World and even today are an engineering marvel. Their thickness averages 20 feet (6m) at the base and 12 feet (3.7m) at the top, with an average height of 40 feet (12m). At their top, notice the balconied buildings that served for centuries as hospitals and also residences of the island's various governors. Between Fort San Cristóbal and El Morro, bastions were erected at frequent intervals. The walls come into view as you approach from San Cristóbal on your way to El Morro. (Bus: Old Town Trolley.)

San Juan Cemetery, on Calle Norzagaray, officially opened in 1814 and has since been the final resting place for many prominent Puerto Rican families. The circular chapel, dedicated to Saint Magdalene of Pazzis, was built in the 1860s. Aficionados of old graveyards can wander among marble monuments, mausoleums, and statues, marvelous examples of Victorian funereal statuary. Because there are no trees, or any other form of shade here, it would be best not to go exploring in the noonday sun. In any case, be careful -- the cemetery is often a venue for illegal drug deals and can be dangerous. (Bus: Old City Trolley.)

Historic Squares

In Old San Juan, Plaza del Quinto Centenario (Quincentennial Plaza) overlooks the Atlantic from atop the highest point in the city. A striking and symbolic feature of the plaza, which was constructed as part of the 1992-93 celebration of the 500th anniversary of the discovery of the New World, is a sculpture that rises 40 feet (12m) from the plaza's top level. The monumental sculpture in black granite and ceramics symbolizes the earthen and clay roots of American history and is the work of Jaime Suarez, one of Puerto Rico's foremost artists. From its southern end, two needle-shaped columns point skyward to the North Star, the guiding light of explorers. Placed around the plaza are fountains, other columns, and sculpted steps that represent various historic periods in Puerto Rico's 500-year heritage.

Sweeping views extend from the plaza to El Morro Fortress at the headland of San Juan Bay and to the Dominican Convent and San José Church, a rare New World example of Gothic architecture. Asilo de Beneficencia, a former indigents' hospital dating from 1832, occupies a corner of El Morro's entrance and is now the home of the Institute of Puerto Rican Culture. Adjacent to the plaza is the Cuartel de Ballajá, built in the mid-19th century as the Spanish army headquarters and still the largest edifice in the Americas constructed by Spanish engineers; it houses the Museum of the Americas.

Centrally located, Quincentennial Plaza is one of modern Puerto Rico's respectful gestures to its colorful and lively history. It is a perfect introduction for visitors seeking to discover the many rich links with the past in Old San Juan.

Once named St. James Square, or Plaza Santiago, Plaza de Colón at the main entrance to Old San Juan is at times bustling and busy, but also has a shady, tranquil section. Right off Calle Fortaleza, the square was renamed Plaza de Colón to honor the 400th anniversary of Christopher Columbus' so-called discovery of Puerto Rico, which occurred during his second voyage. Of course, it is more politically correct today to say that Columbus explored or came upon an already inhabited island. He certainly didn't discover it. But when a statue here, perhaps the most famous on the island, was erected atop a high pedestal, it was clearly to honor Columbus, not to decry his legacy. There are some benches beside a newspaper stand in a shady part of the plaza that make a great place to sit. You can grab something cool to drink from a corner store.

Plaza de Las Armas is located at the heart of Old San Juan. The main square is home to San Juan City Hall, built in 1789 as a replica of the Madrid City Hall, and the Puerto Rico State Department, in a beautiful colonial building from the 18th century. The plaza also has a fountain (which unfortunately is usually not working) with four statues representing the four seasons and some gazebos and a cafe. The Cuatro Estaciones, or Four Seasons, cafe is a nice spot for a strong cup of coffee or a cold drink. In a recent renovation, large trees were planted in the plaza, which provides blissful shade in several spots.

The Paseo de la Princesa is a wide bayside promenade with outstanding views. The walkway runs along the bay beneath the imposing Spanish colonial wall that surrounds the Old City. It takes its name from a prominent building along it, La Princesa, a former prison in the 1800s that has been blissfully restored and now houses the Puerto Rico Tourism Company Headquarters. The sexy fountain at its center, "Raíces," or "Races," shoots powerful streams of water over the bronze naked Adonises and Amazon warrior goddesses riding huge horses and fish, so you'll get wet if you get too close. Spanish artist Luis Sanguino undertook the work as part of the 500th anniversary of San Juan's founding. The statue is meant to show the Taíno, African, and Spanish roots of Puerto Rico and its people. Farther along, the promenade bends around the bay and passes a shaded area before heading down to San Juan Gate. The new El Morro trail, which goes around the base of the fortress, is actually an extension of this promenade. There are food and drink vendors and often artisans selling their crafts, especially at the start of the route near the cruise ship docks. Enter near the cruise ship docks at the corner of Recinto Sur and Calle La Puntilla or via the San Juan Gate (Calle San Francisco and Calle Recinto Oeste).

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.