Old San Juan was founded in 1521, a century before the Pilgrims landed on Plymouth Rock. San Juan’s history is evident at every footstep: if you look down, the blue cobblestone streets (called "adoquines") in Old San Juan are constructed from ballast used by Spanish galleons. The hundreds of colonial buildings in San Juan are not just “colonial” in style; they are original constructions that once housed merchants and nobility in the New World’s richest port of call (hence, “Puerto Rico”, the original name for the City of San Juan).
Today, Old San Juan is the principal port-of-call for the entire Caribbean. It is one of three tourist areas in San Juan (Condado, Ocean Park, and Isla Verde being the others). Old San Juan is best known for its architecture, shopping and restaurants, while Condado is best known for its nightlife and shopping. Isla Verde is known for its beaches and resorts. Visitors will feel welcome and comfortable strolling through Old San Juan.
The Old City is HOT (literally). The weather in Puerto Rico is tropical. Unlike Condado, Ocean Park, and Isla Verde, Old San Juan faces San Juan Bay on a slope overlooking the Caribbean. This means that there are no cooling winds (except for area around El Morro). If you are visiting before 6 p.m., wear sneakers and leave the flip flops and high heels at the hotel. After 6 p.m., you should be aware of the dress code for high end establishments which sometimes require more formal attire.
Old San Juan (“The Old City”) it is actually a walled city within a city. Old San Juan (Viejo San Juan in Spanish) is a peninsula which is connected to the mainland by bridges. How you arrive to the Old City is important. If you are arriving on a cruise ship, you will be landing at the southern portion on the bay side. If you are arriving from the airport, you are driving into the Old City or taking public transportation.
Since Old San Juan is built on a steep hill, plan your sightseeing accordingly. The east-west streets are level, but north-south streets are extremely steep. Nearly all the streets are paved with adoquines. High heels and adoquines have never gotten along well together.
Public transport to the Old City is easy. La Bochinchosa's bus route map displays bus routes to Old San Juan. Returning to San Juan is just as easy; go to the bus terminal located near the piers at the corner of Paso Covadonga and Calle Juan Antonion Coretejas. The buses are immaculately maintained, safe, and air-conditioned.
Within the Walled City, a free handy tourist trolley traverses the city between El Morro and Plaza Colon. Since the Walled City is on a hill (the southern piers being the bottom and El Morro and Bulevar Del Valle being the top), the mobility challenged might elect to forego exploring and target specific sights on the trolley line. On a hot day, most tourists will benefit from riding up the hill to El Morro, and then starting their exploration downhill.
If you start your tour at El Morro,here is garage parking at the Plaza del Quinto Centenario near the entrance to El Morro that almost always has parking spaces available. This is unknown to most tourists, who seek out parking near Plaza Colon or Calle Princesa. Like most congested urban areas, parking spaces are gold. Don’t attempt to find street parking; it’s impossible in the Old City during the height of tourist season. Parking is much easier at the top between San Cristobal and El Morro, the only downside is that you have to walk back up the hill (or take the free trolley) to return to your car. Under no circumstances attempt to drive through the Old City, especially in a car larger than a compact. The 500 year old city was not designed for traffic, and even locals have difficult navigating the Old City.
The Walled City west of Plaza Colon is entirely safe (and in general quite upscale). You should have no security concerns about visiting the Old City. There are a few vacant run down buildings between Calle Luna and Calle San Sebastian, but the area has virtually no serious crime and certainly no violent crime. in fact, Calle San Sebastian on weekends becomes a large block party.
It is possible to walk from the Old City to Condado (San Juan’s main tourist area) and vice versa. Avoid the southern portion of Puerto de Tierra at night. During the day, the walk along Ave. Munoz Rivera on the northern shore overlooking the ocean is spectacular.
Never venture into La Perla. La Perla is the section below the castle walls between El Morro and San Cristobal on the north side of the city. It is accessible only by a single road and a handful of entrances through the castle’s fortifications. The La Perla area is a pariah in the San Juan Community which even the Police take pains to avoid.
The Old City is compact and walkable. It exudes its 500 years of history. You will marvel at the architecture. Many of the fine old buildings have thirty and fifty foot ceilings (gilded, encased in wrought iron, or mosaic) which rise to hold spectacular interior atriums. Even smaller private homes and three story buildings often have these interior atriums. When walking through the Old City, take time to peer through a doorway or passageway. More often than not, the small entrance will lead to a grand courtyard or shared market space. Much of Old San Juan is hidden deep behind the walls which face the street, and half of the fun is discovering these hidden “gems”.
Most tourists stay on Calles Forteleza, Tetuan, and San Francisco. Definitely walk these streets, which form the main east-west corridors. But venture into the side streets, particularly Calle del Cristo. The area two blocks east and west of Calle del Cristo at its very southern tip is easily one of the most romantic spots in Old San Juan. At night the scent of local island flora and sea spray create a surreal experience as moonlight dances across a tropical lagoon just below. By day, this street south of El Convento is laden with shade-giving trees that lend a mystical aura to this hidden and seldom-visited area.
El Convento, in 1962 a catholic convent was converted to a hotel and renamed “El Convento” (“The Convent”). While the hotel portion of El Convento is restricted to guests, but the interior atrium is a small maze of restaurants and bars open to the public. In the vein of Babylon’s hanging gardens, you can walk around one of the interior mezzanines and look up to see vines clinging to terraces, or glimpse down into an atrium boasting plants, trees and a fountain.
El Morro is one of two fortresses which mark the entrance to the San Juan bay. It wa the original fort for San Juan and was later extended to include its counterpart, San Cristobal. Getting to the castle requires a walk of more than a quarter mile across rare open urban space. The area surrounding El Morro is open to ocean winds from all sides. On a hot day, it is the best place in the Old City to catch a breeze, but be advised that the only shade available is inside of the castle itself. San Cristobal features sweeping views of the ocean and San Juan. Both Forts are distinct and well worth a visit.
Restaurants in the Old City are abundant. If you are seeking an authentic “native” experience with a firepit and cheap beer, Pinones might be a safer bet. Old San Juan is a cosmopolitan and polished city. Cheap eats and pubs are available, but more often than not they serve foreign fare: Jamaican, Haitian Irish, Italian, even Moroccan themes are as common as Puerto Rico-styled venues. Upscale restaurants tend to focus more on local cuisine, but there is a restaurant in a price range for any palette. San Juan has been welcoming out-of-towners for five centuries; it’s not a stretch to call the Walled City a “United Nations” for foodies.
You will find everything from Marshall’s to native local art in Old San Juan. Bargains are available, but for interesting and unusual items, Old San Juan is your best bet while in San Juan. Whereas Condado stores focus on serving high-end clients, Old San Juan shopping is best described as “eclectic”. The vast majority of stores are on Calles San Francisco and Fortaleza between Plaza Colon and Calle Cruz. Old San Juan has the most compact and diverse shopping experience in the Caribbean.
Spend at least one day in the Old City (in comfortable shoes) and pick up those obligatory souvenirs. For a true Puerto Rican experience, shop around and treat yourself to a vejigante.