San Juan is the capital of and largest city in Puerto Rico, with a population of about 395,000. It has one of the best harbors in the Caribbean. The city celebrates its fifth century in 2008 or 2021, depending on whether one counts from the founding of the original settlement at Caparra or the act of moving the

Caparra settlement

to Puerto Rico isle (now

Old San Juan

).

Understand

Location
San Juan is the oldest city under the jurisdiction of the United States. San Juan is in the northeast of the island of Puerto Rico, and features distinctly century-old architecture, such as Spanish military forts built from the 1540s to 1800s, an active harbor, and a very active economic area in the Hato Rey district. It features magnificent beaches, hotels, plazas, historic sites, museums, and so on.
San Juan has a land area of about 76 square miles. The city's population is approximately 395,000.
Culture
San Juan is a Latin American city with Spanish-based culture mixed with African traditions, Taíno culture, and an American influence. Museums of modern art exist abroad. The citizens of San Juan are very festive, as on the rest of the island. San Juan has bars and discotheques all around the city, from Old San Juan to even the southern part of the city, that stay open to 3:00 or 4:00AM. San Juan has become very modernized as of late, with its first metro train line (called Tren Urbano) and buses. Poverty and crime remain significant issues.
San Juan is the financial capital of Puerto Rico. There are facilities for petroleum and sugar refining, and pharmaceuticals.

Get around

There are pros and cons to the various methods of getting around San Juan.
Rental car
Getting around various parts of the city, and the rest of the island, as well as to and from the airport, will be much more convenient with a car. Though road signs are in Spanish, the road sign shapes are going to be as familiar to you if you are used to American road signs. And when you see the word norte sitting above a numbered-road sign enough times, it won't take you long to realize that means north. However, a car may entail paying parking fees as you travel around to your destinations so you will need to budget for that. If you go to Old San Juan, parking may be expensive and quite difficult (see that article for how to find the few parking garages there).
Driving in San Juan is very similar to driving in Florida or the cities of the northeast U.S. like Boston or New York. People drive quickly, change lanes with little notice, and frequently tailgate, despite narrow streets. Natives of areas with more placid driving styles like the U.S. Midwest may find it frightening, though.
None of the rental car agencies are within walking distance of the terminals, and the shuttle pickup curbs are not clearly marked or signed, so don't be afraid to ask for help in finding them. Avis and Hertz have their lots located on the airport grounds less than a quarter of a mile from the terminals, and the shuttle trip to and from their facilities is quick and predictable. All other agencies, including Thrifty and Dollar, are located at least one mile away or farther out. You must budget that extra 20 minutes into your planning or you may miss your return flight.
If you are a resident of the United States, check with your auto insurer to see if it already covers you in PR - most do. However, while that means you can decline the collision insurance, you should still take the loss damage waiver (even though it's expensive) as auto collisions in Puerto Rico are common (you will see a lot of dented fenders) and parking spaces in PR are not as large or forgiving as those on the mainland.
Puerto Rico is still using simple paint to mark lanes rather than modern thermoplastic striping. Unfortunately, paint fades fast in the tropical heat and rain, so road markings are hard to see or completely worn away on many roads. In poorer neighborhoods of San Juan, look out for missing manhole covers and huge potholes.
Like much of Latin American and the Caribbean, proper street signs aren't on every corner of San Juan, which makes a good street map (with landmarks) or a GPS navigation system essential. Only

Condado

and Ocean Park have excellent street signage comparable to those taken for granted in mainland U.S. cities.
The closest place to refuel a rental car before returning it is the Puma gas station on the frontage road ("Calle Marginal") off eastbound PR-26 (Expreso Loiza), at the intersection with Calle Heriberto. Once you're done there, you can continue down the road to Thrifty or Dollar, or keep going to the next underpass to loop around and head west towards the airport.
By bus
The public bus system in San Juan is inexpensive at only 75 cents a ride. Only coins are accepted on board so stock up on those quarters! (5c and 10c coins are fine too). The bus stops are marked "PARADA", and the system is currently being reworked to fit in with a new train line. If you're planning on staying in and around a general area of San Juan, you may be able to get by on public transportation. When you see your bus coming, be sure to wave/flag it down otherwise it may just pass you by!
Take notice; contrary to some bus schedules (even ones posted at the bus stops themselves) that state buses may arrive every 15 minutes or so, service can be infrequent and very unpredictable. You may wait anywhere from 5 to 30 minutes for a bus to arrive. Rush hour buses can be very full. Additionally, traffic gets very heavy heading into Old San Juan, so once you board the bus you still are not guaranteed a quick trip. If going into Old San Juan, some useful bus routes include T3 (from Sagrado Coazón train station), T5 (from Isla Verde via Miramar), T21 (from Condado), and D53 (from Luis Muñoz Marín International Airport via Isla Verde and Condado). Old San Juan, near the harbor front, has a major bus station for catching numerous routes.
Visitors may find that bus routes directly to and from places of interest around San Juan do not exist, and that a transfer with additional waiting times are involved. Plan your trips wisely as most routes work Monday through Friday from 5:00AM to 9:00PM; and Saturdays and holidays from 6:00AM to 8:00PM. T3 and E40 express route are the only two routes that offers service on Sundays. The T3 route works everyday from 5:00AM to 11:00PM; and the E40 from 5:00AM to 8:00PM. Only If you have little time to see/do what you'd like, you'd be better served using a taxi or renting a car.
Also, have in mind, if you are planning to get back to the airport by bus, some bus drivers may not let you board the bus if you carry-on more than one baggage. You may want to plan in advance to take a taxi back to the airport if your hotel has no shuttle. Carrying baggage on the city bus tends to be less of an issue when you initally head from the airport. Three routes serves Luis Muñoz Marín International Airport: E40 express route (to Piñero train station), T5, and D53 (to Old San Juan, Condado, Isla Verde, and Puerto Rico Convention Center).
Check with AMA to inquire about routes and times. Also, for train and buses time tables you can download Tren Urbano App (unofficial app) for iOS and Android phones.
There is a free trolley bus routes around Old San Juan - look out for the numbered signs.
As for getting around the rest of the island of Puerto Rico, there are no convenient buses connecting San Juan to the rest of the island. There are vans that are like group taxis with specific routes called "guaguas." You can inquire about trips outside of San Juan at the guagua terminal in Rio Piedras. But keep in mind, guaguas may make multiple stops to maximize revenue, and it could take ages to get you to where you are going on the island.
By ferry
The Cataño Ferry (La Lancha de Cataño) is a public ferry serving Old San Juan and Cataño. It crosses San Juan Bay every 15-30 minutes.
By train
San Juan is served by a rapid transit rail line called "Tren Urbano" (Urban Train). The line connects San Juan to the towns of Guaynabo and Bayamón, but it avoids points of interest like Old San Juan, Condado, and Isla Verde. But if you want to give it a spin anyway:
- Take a city bus to a station, e.g., T3 or the E10 express route from the Old San Juan Covadonga bus terminal to Sagrado Corazón train station.
- Explore the town of Río Piedras by getting off at Universidad or Río Piedras stations and making your way down the colorful Avenida Juan Ponce de León. Explore the side streets and alleys to discover some wonderful street art.
- Get to the airport by taking the E40 express route at Piñero station.
Tickets are $1.50 per ride irrespective of distance. There are ticket machines accepting cash and credit cards at all stations. The magnetic tickets they issue are rechargeable and also usable to pay your fare on the bus. There are discounted fares for students, children and elderly people on both the buses and the train.
For train and buses time tables you can download Tren Urbano App (unofficial app) for iOS and Android phones.
By taxi
Taxis can be found hanging around hotels and the east end of Calle de la Fortaleza in Old San Juan. In theory, they are supposed to be metered (the rates are posted on doors), except for a selection of common tourist routes with fixed fares. In practice, cabbies are well aware that tourists tend to have no idea what those fixed fares are and charge according to what they feel like.
For any issues with cabs, contact the Tourist Transportation Department at 787-999-2100 ext. 4502 between 7:30AM to 4:30PM Monday through Friday.

See

• El Castillo San Felipe del Morro "El Morro" : is a sixteenth-century citadel that lies on the northwestern-most point of the islet of San Juan, Puerto Rico. It is part of San Juan National Historic Site and was declared a World Heritage Site by the United Nations in 1983.
• El Castillo de San Cristóbal, (787) 729-6960. A Spanish fort in San Juan, Puerto Rico. It was built by the Spaniards to protect against land based attacks on the city of San Juan. It is part of San Juan National Historic Site. It covers 27 acres of land and is 150 ft tall. Open every day from 9AM to 6PM.
• Palacio de Santa Catalina "La Fortaleza" (or The Fortress in English) is the official residence of the Governor of Puerto Rico, who is Puerto Rico's head of Government. It was built between 1533 and 1540 to defend the harbor of San Juan. The structure is also known as El Palacio de Santa Catalina (or Palace of Santa Catalina). It is the oldest executive mansion in the New World. La Fortaleza was declared as a World Heritage Site by UNESCO.
• El Cathedral de San Juan Bautista: contains the tomb of the Spanish explorer Juan Ponce de León. It was built in the 1520's, soon to be wrecked by a hurricane, and then rebuilt in 1540. After being rebuilt, it was robbed in the late 1500's, and then, in 1615, it was damaged by a hurricane. In 1917, a lot of changes were made to restore the building. Tours are given daily from 8:30AM-4PM.
• Castillo de San Jerónimo is a small fort located in the entrance to what is known today as Condado, Puerto Rico lagoon in San Juan. The fort defended San Juan from attacks by Sir Francis Drake in 1595, Sir George Clifford "Earl of Cumberland" in 1598 and Sir Ralph Abercromby.
• Iglesia de San Jose dates back to 1523. This building was originally called the Church and Monastery of Saint Thomas Aquinas. Before Ponce de Leon was moved to the San Juan Cathedral, his body was buried here for 300 years.
• Ayuntamiento or Alcaldia or City Hall.
• The municipal cemetery of Santa María Madgalena de Pazzis, located just outside the city walls.
• Fuerte San Geronimo is a fort that was built to tighten defense within the city. There is a small museum inside.
• Centro de Bellas Artes is the largest fine arts center in the Caribbean. Concerts, Plays, and Operas are hosted here. This fine arts center opened in 1981.
• Bacardi Rum Factory, (787)788-8400, M-Sa 9AM-4:30PM, Sunday from 10AM-3:30PM. Also called the "Cathedral of Rum" and covers 127 acres. Free tour, including a trolley ride around the premises.

Do

Check out the beaches in Condado and Isla Verde.
A popular point of interest is Old San Juan, a 7-block area that has become popular for tourists as well as residents. The narrow streets of old San Juan are packed with people so it is recommended to experience Old San Juan by foot in order to avoid too much traffic. You can take a taxi for less than $20 from most hotels but for .75 you can also take the B21 bus which picks up from many locations near the hotels and is very easy to use.
Check out the parks in San Juan.

• Central Park is the park to visit if you're looking for traditional activities such as jogging, tennis, baseball, etc.
• La Marquesa Canopy Tour - Located about 30 minutes outside of San Juan in Guaynabo you can tour the La Marquesa Forest Reserve via zip line. It is a low impact experience suitable for people of all ages. Those who are up for extreme adventure travel may find this a little too easy.
• Garfield, 7558 calle del cristo (go far west), (787)721-2500. 
• Munoz Rivera Park, Av. Ponce de León. Tu-Su 9AM-5PM. Located by the ocean and has beautiful trees and landscaping. A great place to tour by foot.
• Parque de las Palomas overlooks La Princesa Jail. From this park you are able to see a great view of the mountains, harbor and the city.
• The Casino of Puerto Rico is a large building with a 12 foot chandelier and an open ballroom, built right before World War I.
• The Teatro Tapia, (787) 721-0169 or (787) 721-0180. Built in 1832, this is one of the oldest theaters in the Western Hemisphere. This building, which was named after Alejandro Tapia y Rivera, has been remodeled twice, once in 1949 and once in 1987. Plays, ballets, and other concerts and events are held here.
• Flavors of San Juan Food and Culture Tours, Old San Juan, 787-964-2447, 10am-1pm (tues-sun) & 4:30pm-7:30pm (tues-sat). Local tour operator running daily foodie walking tours, as well as cooking classes and rum tastings. Flavors of San Juan gives an exclusive taste of local food, rum, and coffee in the most memorable restaurants and streets of San Juan. They take you away from the tourist traps to discover the history, the sweet secrets, and the savory enclaves that San Juaneros call home. 

Buy

• The Butterfly People, 257 Calle de la Cruz, Old San Juan, Phone: 787-723-2432. Real butterflies encased in acrylic. Stunning. Go to see it, even if you don't buy.
• Plaza las Américas, "The Center of it All", biggest mall in the Caribbean, containing more than 300 stores anchored by the world's largest JC Penney, plus Macy's, Lacoste, American Eagle, A|X, Sports Authority and Sears. It has a movie theater and restaurants such as Chili's, Macaroni Grill, Margarita's and Tierra del Fuego. If you need or want to visit a good example of a modern, enclosed mall from the U.S. mainland, this won't disappoint.
• Old San Juan, Shopping in Old San Juan is diverse, with retailers scattered among many narrow streets. Stores include many fine jewelers, arts, crafts and mercantil shops, at least one drug store, and a few branded "outlets". You'll also find numerous cafes and a few fine restaurants. For walkers, the humidity and tropical sun may make the mid-late afternoon temperatures a bit oppressive. Alternatives include going early as stores open (typically 10AM on weekdays) or catching a 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.

Eat

• Al Dente, Calle Recinto Sur 309, Old San Juan, Phone: 787-723-7303. M-F 12PM-3PM; M-Sa 6PM-11PM; Sun 12:30PM-4PM and 6PM-10PM. The oldest continuously operated Italian restaurant in Puerto Rico.
• Café Puerto Rico, Calle O'Donnell 208, 787 724-2281. 11:30AM-11PM. Creole cuisine. On the Plaza de Colón, enjoy the view along with a great meal. Great spot to stop for a drink, snack & conversation too. Live music weekends & some weekdays. Recently expanded to the second floor. Best meal: stuffed snapper (fillet + lobster, crab, shellfish in a flavorful broth) + rice & beans + sweet plantains. $9-$21 main course but order side dishes too.  
• El Alcázar, 1013 Ave. Roosevelt. New Spanish restaurant which serves a variety of "Tapas", seafood and several meats. Also has a variety of Wines. The ambience is romantic and live music is offered several times a month.
• El Asador, The Grill Old San Juan 350 San Francisco St. (Old San Juan, Puerto Rico 00902), 787-289-9966, 10AM - 4AM 7 Days a Week. El Asador Bar Restaurant The Best Meats Cuts & Puertorrican Cuisine located at the entrance of Old San Juan, the heart of nightlife in the Old City. It is the most stylish and exclusive Bar Restaurant in San Juan, a two level Restaurant with an exterior patio the perfect environment for an exciting experience. Delight with an early lunch or a romantic dinner in one of the most beautiful interior patios of the Old City, or why not enjoy the best music and liveliest party in San Juan until sunrise. El Asador is a cozy and sophisticated Bar Restaurant, patronized by upscale, trendy, local and tourist.
• Luigi's Restaurant, 104 Diez de Andino, Condado, 787-722-2672. M-Sa 11:30AM-3PM and 6PM-10PM; Su 12PM-5pPM. Serves Italian and Genovese cuisine.
• Margarita's, Several locations including 3rd level at Plaza las Américas and 1013 Ave. Roosevelt, 787-792-0283. One of the traditional Mexican food restaurants that exists in the island.
• Milagros y Sean's, Isla Verde. Delicious traditional home cooked Spanish food and half-edible Irish cuisine if you're not in the mood for good tasting things. Bartender makes great cocktails and pours a terrible Guiness. Lounge area with 90's hip-hop, R&B classics, and semi-tolerable fiddle.
• Ostra Cosa, Calle del Cristo 154, Old San Juan, 787-722-2672. Daily 12PM-10PM. Reservations recommended. The ambience here is one of the most sensual and romantic in Old San Juan.
• Pamela’s Caribbean Cuisine, 1 Calle Santa Ana Ocean Park, San Juan Puerto Rico 00911, (787) 726-5010. Lunch 11AM to 3PM, tapas and appetizers 3PM to 6PM, and dinner from 6PM. Pamela’s Caribbean Cuisine is an award-winning San Juan restaurant popular for special occasions. Adjacent to Numero Uno Pamela’s is known not only for its exquisite Caribbean-fusion menu, but also for its one-of-a-kind beachside location.  
• Parrot Club, Calle Fortaleza 363, Old San Juan, 787-725-7370. Daily 12PM-3PM; 6PM-11PM. Live music, either Brazilian, salsa, or Latino jazz, is offered nightly as well as during the popular Sunday brunches.
• Ramiro's, Av. Magdalena 1106, Condado, 787-721-9049. M-Sa 12PM-3PM & 6PM-11PM; Su 12PM-3PM & 6PM-10PM. Creole" style cooking pioneered by owner and chef Jesús Ramiro.
• San Juan Hard Rock Café, Old San Juan.
• Tantra is located at 356 Calle Fortaleza and serves international cuisine. Great creative and nightlife atmosphere. A warm, candlelit environment with great food and great martinis. Moderately priced, entrees run from around $13-$17. (787)977-8141.
• Tierra del Fuego, 3rd Level at Plaza las Américas, 787-294-7019. One of the best Argentinean restaurants where you will be able to savor a tender, juicy cut of meat prepared by chefs and cooks who, together with the warm staff of waiters and hostesses, are without representation of a trade union that can defend their rights of having fair wages and benefits.
• UVVA Restaurant, (787) 727-3302, 1 Calle Tapia, Ocean Park. International creative cuisine by Chef Jose Vicente is served from 8AM until 11PM. The ambiance is elegant and casual.
• BUNS Burger Shop, 1214 Ashford Ave. (In front of Marriott Hotel). 11:30am-4:00am. Great burgers with high quality beef. Over 40 beers, some on tap.  

Drink

• Brava, At Wyndham El San Juan Hotel & Casino, Isla Verde. Cover $15, free for residents of El San Juan Hotel. Open Th-Sa from 10PM until 4AM.
• Cigar Bar, At Wyndham El San Juan Hotel & Casino, Isla Verde. Daily 6PM to 3AM.
• Club Laser, Calle del Cruz 251, near the corner of Calle Fortaleza.Cover $8-$12 (free cover for women before midnight on Sat) The club is usually open Th-Su from 10PM until 4AM.
• Dákiti, Calle San Sebastián, Pub with two floors. Idilic for the San Sebastián Festivities.
• Dragonfly, Restaurant and bar on Forteleza Street in Old San Juan.
• El Patio de Sam, Calle San Sebastián, Old San Juan. One of the most popular late-night joints with a good selection of beers. Live entertainment is presented here M-Sa.Open daily noon to 1AM.
• Logan's Irish Pub, Calle Bori 496, Río Piedras. Daily 11:30AM to 1AM (closes at 2:30AM F-Sa). A sports bar with TV monitors and high-energy rock 'n' roll.
• Rumba, Calle San Sebastián 152. The site for the filming of many of the crowd scenes within Dirty Dancing: Havana Nights. Cover $15.
• Shannon's Irish Pub, Marginal Martínez Nadal, Guaynabo. Daily 11:30AM to 1AM (closes at 2:30AM F-Sa). A sports bar with TV monitors and high-energy rock 'n' roll.
• Nuyorican Cafe, Calle San Francisco #312. 787-977-1276. Good live music venue in Old San Juan. Salsa, Latin jazz, folkloric music.
• Ristorante Pinoli, 404 De Diego Ave. Puerto Nuevo (Just off Roosevelt Ave. on the right), 787-273-1611, 12-3 6-10. This is one of the finest Italian restaurants in Puerto Rico. The menu is very creative with new dishes added based on the fresh ingredients available on any given day. This is a cloth napkin establishment. 
• BUNS Burger Shop, 1214 Ashford Ave. (In front of Marriott Hotel). 11:30am-4:00am. Great burger place with over 40 beers. High quality beef is their priority.