San Juan/Old San Juan
Old San Juan (Viejo San Juan) is the historic core of San Juan. Although this eight by ten block district is part of San Juan, it is quite geographically and culturally distinct from the rest of the city. It occupies the western half of the islet of San Juan, which it shares with Puerta de Tierra. As this is a tourist destination, English is relatively common, but not universally spoken.
Founded in 1509, San Juan became a walled city protected by multiple forts. It guarded an important entrance into the Spanish Main, and withstood multiple attacks by the British and Dutch (some partially successful). It was considered the Gibraltar of the West Indies. Due to its military significance, the government kept the growing population within the city walls until 1897, when a few bastions were demolished. The forts received some naval bombardment from US naval ships during the Spanish American War (1898). Much of the district is intact architecturally, including the impressive fortifications.
Many tourists are caught unaware by the sun exposure received from simply walking around the sites of this tropical city. Sunblock is available at many stores in town. Wear good walking shoes to deal with the hills and cobblestone streets. Around the perimeter of the district the trade winds make it surprisingly comfortable, but along the interior streets it get much hotter, with closely spaced, multi-story buildings cutting off any breeze. Brief showers are quite common, so watch your step, the cobblestones can get quite slippery.
Old San Juan is a common stop for cruise ships, yet it is definitely not a beach resort. It is a real town within a city, where people work and live. Men typically wear collared shirts and long pants, and businessmen wear suits. Women tend to wear skirts or dresses and often high heeled shoes. Although visitors are expected to dress more casually; a collared shirt, shorts with pockets and belt, and shoes are minimally appropriate for adults at most attractions.
Today the port of San Juan annually accommodates nearly 1.4 million passengers in cruise ship travel alone, making it the third busiest cruise port in the world, according to the Cruise Industry Statistical Review published in 2000. The busiest docks are on the south side of the area near a large city bus station. Another pier adjacent to the old Pan American airport handles mostly Royal Caribbean cruise ships for beginning or ending their cruises; it must be reached by car or taxi. Otherwise, all cruise ships dock at Old San Juan.
You may arrive at San Juan/Luis Muñoz Marín Airport, then take a $20 cab ride to your pier. If cruising, you should reach San Juan at least a day before the cruise ship embarks to ensure you make it despite any airline troubles. This also provides time for sightseeing in Old San Juan, near your hotel, etc.
There is also ferry service from across the harbor. Although one can easily drive to Old San Juan, it is not easy to drive or park within the district due to the narrow streets.
For those staying at major hotels outside Old San Juan, day tours can usually be arranged with the concierge. During busy times, drivers may refuse those with significant luggage. For just getting around, you might also consider the city bus to and from Old San Juan. (see same subject for "San Juan")
Old San Juan is primarily made up of one-way cobblestone roads, and parking is practically non-existent. If you must drive, try to drive and park along Calle de Norzagaray or any other streets on the northern side, and park there if you can. It is near the main attractions and the trolley system which can take you into Old San Juan and out back to your car when you are done.
It is $20 to go within Old San Juan by taxi, and this option may be best if you are not practically dressed or not in comfortable walking shoes, or traveling as someone or with someone who cannot walk long distances easily.
By public transportation
Buses do not actually go into Old San Juan, and one walk across the cobblestone roads will show you why. However, they do serve a major bus station on the harbor side of the area, near one of the major cruise ship piers. There is a free, often-running trolley that takes people around the forts, museums, and the center of Old San Juan. Trolley stops are marked with yellow banners that show an illustration of a trolley and a number that indicates which stop it is. You can get on or off at any designated stop, and the trolley driver will help you find your stop if you aren't sure. If you're feeling a bit warm in the midday heat, hop on a white trolley which is open on the sides to catch a nice breeze while speeding to your destination. On Saturday and Sunday afternoons, when cruise ships bring in hundreds of tourists, the trolley is often completely full and does not pick up new passengers. Try to go early.
The attractions of Old San Juan are technically within walking distance of each other, although the climate and topography can make this untrue in practice. Even if the locals wear nice shoes or sandals, you should wear comfortable walking shoes, as you will scale a few hills and a lot of cobblestone while getting around. Even within the pedestrian metropolis that is Old San Juan, cars will speed through intersections, so use the same amount of caution as you do in other parts of San Juan and wait for cars to stop for you. Do not try to stop traffic unless it is urgent that you cross the street, and if you must then make sure you have made eye contact with the driver and there is no possibility that the car behind it can bypass him from the side and proceed across the intersection. Sidewalks are very narrow and sometimes may have grooves or tripping hazards, so be careful.
While definitely part of Old San Juan's charm, the identical-looking architecture of Old San Juan's buildings can be a nuisance to tourists trying to use landmarks or memory to find something. Don't wait to get to Old San Juan to get a map, get one beforehand and study it so you know what streets take you to your destination and what streets don't. Don't try to use landmarks until you are used to navigating the city, especially since the heat and tiredness from walking can wear you out more quickly than you think. If you get lost or confused, find a bench and pull out your map, which should be readily available to you. Locals will also try to respond to simple requests for help. Don't try to walk yourself back into familiar territory. If you are trying to find a specific museum or restaurant that is not one of the major ones, memorize the address and street. If you know exactly where you are and where you are going, you should find navigating Old San Juan on foot very easy and enjoyable.
Shopping in Old San Juan is diverse, with retailers scattered among many narrow streets. Stores include many fine jewelers, arts, crafts and mercantile shops, two drug stores, and a few branded "outlets", e.g., Coach...genuine with good prices, but discontinued styles. You'll also find numerous cafes and a few fine restaurants. You'll find a well-stocked Walgreens (Rx services pending) at the corner of a large square in the central area, and a new/large CVS (with Rx services) opposite the cross-bay ferry terminal.
Mid-late afternoon temperatures may make walking a bit oppressive, with tall, crowded buildings blocking any breeze. Alternatives to avoid the humidity and tropical sun include going early as stores open (typically 10AM on weekdays) or catching the free trolley winding throughout the area, with opportunities to get off at marked stops wherever desired. The trolley tends to stay very full on afternoons when cruise ships are in.
Unlike in most U.S. States, Puerto Rican laws make it easy for restaurants to sell alcohol. Even modest lunch counters will offer beer, wine, and some mixed drinks. Tipping is customary. There are restaurants which cater to tourists, particularly tapas bars and Latin "fusion" restaurants, but look at the menu before going in to make sure prices are in a comfortable range.
There is a public ordinance which bars drinking alcoholic beverages on the street. Although this is rarely enforced, it is recommended to consume all alcoholic beverages inside the establishments. This local ordinance is relaxed during the San Sebastian Carnival, where drinking in public areas will be allowed if using containers purchased at official establishments.
Although Old San Juan is almost entirely surrounded by water, no hotels have beach access. A few modern chain hotels are located near the cruise ship docks, some with casinos. Hotels within the city walls tend to be more colorful.
Within the city walls, Old San Juan is quite safe. On the southern waterfront by the piers where cruise ships dock, local police line the area, keeping it safe for tourists, even at night. Along this waterfront and in front of the Sheraton hotel is the best place to catch a taxi at night if you need to.
Tourists should be aware that a small neighborhood, La Perla, between the northern city wall and the ocean is a private community and not a tourist area. Visitors should avoid this area since it is a neighborhood of poverty and drug trafficking. La Perla is quite isolated from the attractions that line the northern part of the city and very visibly slummish and different looking amd separated from the rest of Old San Juan by the city walls, so it is not easy to accidentally wander into that part of town. The only thing that may bring tourists too close to La Perla is the Cementerio de Santa Maria Magdalena, which borders the neighborhood and lies at the bottom of the large grassy field behind El Morro. Try not to go into the cemetery unless you have business there, and never visit at night. Visiting photographers should also resist the temptation of going into La Perla to photograph the boldly colored, stacked shacks in various states of decay. To get the best views of La Perla without putting yourself in danger, take the trolley going north on C. de Norzagaray and sit on the left side, or try the lookout views from San Cristobal.
While safe during the daylight hours, at night it is also best to avoid the bastions of the northern city wall that overlook La Perla. As in any other foreign city, it is not advisable to go out alone late at night, unless you have a friend or guide to escort you. If you are traveling by bus, understand that buses that service stations in many of the outlying hotel areas stop running at around 9 or 10PM, and the exact time of the last bus is never sure. If you plan on being out at night in Old San Juan and you are taking the bus in, bring enough money for a taxi in case you stay out too late. Make sure you confirm with your hotel the price you should pay to get back, as cab drivers in Old San Juan are probably the most likely to add a dollar or so to the set fare. Many of the major resort hotels in the area have casinos, lounges, and discos with live music and restaurants which are mostly open until 3-4AM, along with taxis lining the entrance to take people back to their rooms when you're done.
For those staying in Old San Juan, organized bus/van day-trips to other sights in Puerto Rico can be arranged through most hotels.
Some cabs wait at the end of the El Morro esplanade footpath. There are usually many, many cabs standing at the southwest corner of Plaza Colón.