The quaint Old Town of San Juan, Puerto Rico is a vintage Spanish American community and is loaded with enough attractions, restaurants, and shops to warrant at least a full day of sightseeing.
My walk begins at the cruise ship docks, at the south end of the city, since most visitors arrive this way. Turn left (west) at the road (Calle Concepcion de Garcia) which leads to a cute little square and the Tourist Office. Stop here to get a map of the Old Town before proceeding.
From the entrance to the Tourist Office, turn left. Admire the pastel-colored Custom House to your left, on the water. Turn right and enter the large Plaza de la Marina which marks the eastern end of one of the city’s wonderful promenades, the Paseo la Princessa. Enter this attractive, tree-lined walkway and walk west, noticing several interesting sculptures. The building on the right side (La Princessa) was once a dreaded prison.
Continue to the beautiful, elaborate fountain, which is entitled Roots and depicts the origins of modern-day Puerto Ricans, with dolphins at their feet.
Turn right at the fountain and follow the seaside promenade which winds along the formidable City Walls. As you pass through the San Juan Gate, turn right onto Calle Recinta del Oeste. At the end of the street, the guarded gates mark the entrance to the Governor’s residence, La Fortaleza.
Retrace your steps and continue on Recinta del Oeste. Bear left when you reach Caleta de las Monjas and find yourself in a small square (Plazuela de la Rogativa). Continue parallel to the City Walls to the fork. Bear right and pass La Casa Rosada, a pink villa. Continue up the steep ramp, then cross the field to El Morro (Castillo de San Felipe del Morro). Visit the fortress, admiring, in particular, its dramatic location on a promontory overlooking the Atlantic Ocean.
Exit the fort via Calle del Morro to its end at a plaza. The pastel buildings on the right include Casa Blanca, built by Ponce de Leon’s son-in-law for him (although he never actually lived here).
From here, travel eastward on Calle San Sebastian to the Plaza de San Jose and its much more modern neighbor, Quincentennial Plaza. Wander both squares and be sure to check out Inglesia San Jose, one of the oldest Christian churches in the New World, built in 1532.
Exit the square at its southwestern end and walk downhill on Calle Cristo. On the left, a few blocks down, is the Cathedral of St John, where Ponce de Leon’s remains are entombed. Continue south, then turn left onto Calle Fortaleza and left again on Calle San Jose. On your right is the Plaza de Armas, the original main square of the city. Check out the "Four Seasons" fountain and San Juan’s City Hall (Alcaldia).
Leave the square by heading east on Calle San Francisco which brings you to Plaza de Colon. The stone column in the square has a statue of Christopher Columbus. Continue east on Calle San Francisco, then turn left onto Boulevard del Valle. On the right is San Juan’s other famous fort, Fuerte San Cristobal.
When your visit to the fortress is concluded, head back down the boulevard, past Plaza de Colon, then right on Calle Fortaleza, then left on Calle Tanca and back to the pier.