Walking Tour: Old San Juan

  • Start Café Cola’o
  • End La Taberna Lúpulo
  • Length 2.75 miles; three to four hours

Start with an early-morning caffeine hit at Café Cola’o next to Pier 2. Stroll west and take in the soaring 12-story elegance of the 1937 Banco Popular building, an art-deco gem at the corner of San Justo and Tetuán. Continue along Paseo de la Princesa, a shaded 19th-century esplanade that tracks alongside the formidable old city walls to the brink of the Bahía de San Juan. If it's the weekend, peruse the outdoor artisans fair.

Turn north briefly on Calle del Cristo, then west on Fortaleza. Here you'll find buildings such as the Palacio Rojo that date back to the height of the colonial era. It's easy to see why this 1792 building is called the Red Palace. Its rouge walls once housed the Spanish commanding officers. Now, retrace your steps to the Paseo de la Princesa through Parque de las Palomas where you can buy some birdseed to feed the pigeons.

Head back down to the Paseo de la Princesa. As you feel the Atlantic breeze on your face, you’ll spy the city’s legendary perimeter wall as well as the imposing bronze Fuente Raíces, which depicts Taíno, European and African gods and goddesses rising amid a shower of cascading water.

Behind the fountain, follow the Paseo de la Princesa as it cuts northwest along the waterfront. In the 17th and 18th centuries, 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.

Pass through the gate and turn right onto Recinto Oeste. This short cobblestoned street leads to the guarded iron gates of La Fortaleza, the governor's mansion and executive office. Head back northwest, taking a moment to gaze out over the water from the diminutive Plazuela de la Rogativa and admire its bronze sculpture of a religious procession.

Follow the leafy Caleta de San Juan up the slope to the beautiful Plazuela Las Monjas, where stray cats stretch and romantic couples linger. On the north side of the plaza is Hotel El Convento, a historic building dating to 1651 and one of Puerto Rico’s grandest hotels, well worth a casual inspection. To the east lies the Catedral de San Juan, a relatively austere religious building whose importance is enhanced by its age (dating from 1540) and the fact that the remains of Juan Ponce de León rest inside.

Cut along Luna for a block before taking a right down San José. Take a left onto San Francisco, which will bring you to the Plaza de Armas, an expansive square with government buildings like the imposing Palacio de la Real Intendencia. Continue east on San Francisco, pausing to window-shop along the way and peek into the Iglesia San Francisco de Asís; arrive at the Plaza de Colón, named for the great Genovese explorer. Cut north up Av Muñoz Rivera and you’ll come to Fuerte San Cristóbal, the old city’s other major fortification.

Walking west along Norzagaray, you can see the faded pastel houses of La Perla, a low-income neighborhood sitting along the tempestuous Atlantic. Hidden in a former market building to your left is the Museo de San Juan. Just west, the intriguing Cuartel de Ballajá houses the Museo de las Américas, which provides a fascinating overview of cultural development in the Americas. Across the grassy expanses of Campo del Morro, picnickers fly kites and the stately fort of El Morro beckons. Stroll the former sentries’ walks for panoramic views of San Juan and the sea.

Head down Calle del Morro to the Casa Blanca, the ancestral home for 250 years of the descendants of Juan Ponce de León and the oldest permanent residence in the Americas.

A stone’s throw to the east lies the Plaza de San José, with its statue of Juan Ponce de León, cast from an English cannon captured in the raid of 1797. More antiquity overlooks the plaza from the north in the shape of the Iglesia de San José, the second-oldest church in the Americas, under renovation since 2003. From here, you'll probably be ready for a cold draft beer at La Taberna Lúpulo.