Tour Old San Juan in Under Two Hours

Tour Old San Juan in Under Two Hours

All cruise ships arriving in San Juan will dock at Port 2 or 3. The newly opened Bahia port will soon offer additional docking facilities. The ports are located on the southern portion of Old San Juan (“The Old City”).

The Perimeter Walls

The Old City is actually a semi-enclosed city dating back to the 16th century. The easternmost wall was disassembled in the early 1900’s. The remaining walls encircle the southern, western and northern ramparts. The Old City is laid out in a grid fashion. East-west streets are level, north-south streets require climbing a steep grade. The southern part of the city is sea-level, the northern portion rises to dizzying heights overlooking the Caribbean and La Perla, San Juan’s famous slum located outside of the city’s northern wall.

Historic Landmarks

The northwest and northeast portions of the city are defined by El Morro and San Cristobal, respectively. These famous forts are a “must-see” for many visitors. Famous historic landmarks include the Casablanca, Ponce de Leon’s original home, San Juan Cathedral, Ponce De Leon’s resting place, and the San Juan Gate.


The Walled City is home to the Caribbean’s most eclectic shopping experience. Calle Fortaleza is Old San Juan’s “main street” with a diverse offering of restaurants, bars, shops, and art galleries. Parallel is Calle San Francisco, offering similar stores and restaurants to Fortaleza. The far western end of Calle Fortaleza and Calle San Francisco is marked by Calle Cristo, home to some of the Old City’s more upscale shopping venues.

Awe-Inspiring Beauty

Paseo de La Princesa is a world-renowned boardwalk which begins only a few steps northwest of the cruise ship docks. La Princesa stretches for about a quarter mile along the southern portion of the walled city, and is packed with street vendors, food carts, and live entertainment on Saturdays and Sundays. As Paseo de La Princesa approaches the ocean on the western edge (it actually is outside of the city’s southern wall), La Princesa veers north along the bottom of the Old City’s western fortifications. First-time visitors to San Juan are inevitably awestruck by the beauty of this section of La Princesa. The street is lined by the ocean on the left, and the imposing walls of Old San Juan on the right. The only entrance back into the city is the San Juan Gate. La Princesa eventually terminates at the foot of El Morro.

Hidden Gems

Many of the Old City’s colonial buildings feature interior atriums, hidden from street view. Part of the fun when visiting the Old City is to find the semi-hidden entrances into the interior vestibules. Many restaurants and shops are located in these cooler interior spaces, often further cooled with fountains and vegetation. El Convento is a local landmark designed around such a large interior atrium.


The Walled City is HOT. Northern breezes are blocked by the imposing northern wall. Navigating the city in tropical heat can difficult even for locals. The City of San Juan offers free trolleys, found two blocks to the right of the cruise ship docks past the Wyndham (two blocks north, across from the Banco Popular on Paseo Cavodonga). The white trolleys take guests past El Capitolio and San Juan’s Memorial Gardens, while the orange and red covered trolleys deliver passengers throughout the city, eventually terminating at El Morro.

More Information

The Puerto Rico Tourism Company has a store front open on weekdays, 9-4 pm just across from the cruise ship docks (take a left until Calle Marina terminates, near the horse and buggy depot).

Other Points of Interest

The Old City is steeped in history, but offers world-famous cuisine and entertainment. Strolling Calle Fortaleza or Calle San Francisco will afford visitors with a solid appreciation of the Walled City, but visitors will have a wide range of lesser known alternatives such as Plaza Las Armas, Museo de Las Americas, and Plaza Colon.