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A dynamic port city with contrasting characteristics, San Juan is a capital of rum and fun, where contemporary life at sleek resorts coexists with colorful traditional ways that convey a distinctly tropical flavor. The district that today is called Old San Juan was the personal vision of Juan Ponce de León. He helped plot the layout of the city, supervised the construction of its massive walls and determined which structures were to be built and where. Situated on an easily defensible isthmus, Old San Juan is bounded by two fortresses: El Morro and Fuerte San Cristóbal.

One of the easiest ways to tour Old San Juan is to head west from the pier. Begin at La Casita, “the little house.” Originally built for the Department of Agriculture and Commerce, the miniature building today is Old San Juan’s main tourist information center. Just down the street is the Tourism Company, housed in a former jail known as LaPrincesa; here there is a gallery of rotating art exhibits. La Princesa is located halfway down the Paseo de la Princesa, a promenade between the bay and the citywall. Lined with trees, benches and kiosks, the walkway was built in honor of the quincentennial of Columbus’ 1493 “discovery” of the island.

Along the Paseo, you can get a close look at the ruins of the massive city walls, which at one time encircled the city. They were built in the early 17th century to protect the city from foreign invaders. Two 40-foot-high parallel walls of solid sandstone blocks were constructed, and the space between them was filled with sand. For maximum protection, the walls’ exterior faces were slanted, their width varying from 20 feet at the base to 12 feet at the top. The Paseo de la Princesa brings you to La Fortaleza (The Fortress), the Western Hemisphere’s oldest governor’s mansion still in use. Completed in 1540 as a defense post against the natives, the mansion has housed 170 Puerto Rican governors; more palatial elements of the house, such as the mahogany staircase, the grand reception rooms and the chapel, were all added in the 19th century. The promenade ends near San Juan Gate, the city’s first ceremonial entrance, used whenever high-ranking government or religious officials visited the island.

The Capilla de Cristo, located where Calle Cristo meets the city wall, is a charming tiny chapel with an exquisite silver altar that is visible through glass doors. The chapel is situated next to the Parque de las Palomas (Pigeon Park), home to hundreds of these busy birds. Near the chapel is La Casa del Libro, an 18th-century house that is now a book museum featuring a fine collection of rare books, many of them over 500 years old. Behind it is the Centro Nacional de Artes Populares y Artesanías (National Center of Popular Arts and Crafts), where you can see and buy a variety of island artworks and handicrafts.

The Plaza de Armas, Old San Juan’s main square, is two blocks away, on Calle SanJosé. Originally the grounds for training troops (hence the name), this 16th-century plaza would later become the city’s principal social gathering place. The square’s four statues, over 100 years old, represent the seasons. On the north side of the plaza is San Juan’s city hall, the Alcaldía, modeled after Madrid’s city hall. Construction started in 1604, but the structure was not finished until 1789. There is a tourist information center here, as well as a small gallery. One block north of the Alcaldía is the Museo del Indio, a museum with exhibits on the indigenous peoples of the Caribbean region.

Across Calle San José from city hall, the Catedral de San Juan is another site of interest. The cathedral’s circular staircase and several rooms featuring Gothic vaulted ceilings were built in 1540; most of the church was redone in the 19th century. In 1908, the remains of Ponce de León were moved here from the Iglesia San José.

The Caleta de las Monjas leads you from the cathedral to the Plazuela de la Rogativa (Plaza of the Procession), next to the city wall. This small plaza with the statue of a clergyman leading three women commemorates a very special event in the island’s history. In 1797, when San Juan was under siege by the British, the city’s bishop led a religious procession of devout women singing and carrying torches. The invaders mistook the scene for the arrival of Spanish reinforcements and quickly decamped.

From here, the coastal road takes you through the gate to the grounds of El Morro and to Casa Blanca, or White House, built for Governor Ponce de León after his home was destroyed by a hurricane. The governor, however, never lived to see it. While it was being built, Ponce de León left for Florida in search of the fabled Fountain of Youth and was mortally wounded by a member of the Calusa tribe; he died in Cuba. For 250 years, his descendants lived in the house. Today, Casa Blanca showcases a landscaped garden and two museums: the Juan Ponce de León Museum, which illustrates what life was like in 16th- and 17th-century Puerto Rico, and the Taino Indian Ethno-Historic Museum, complete with a re-created Taino village.

Uphill from Casa Blanca, the Asilo de Beneficencia was built for San Juan’s poor in the 1840s. Today, the restored structure serves as the headquarters for the Institute of Puerto Rican Culture, with exhibits on archaeology, art and urban planning in the several small galleries. Beyond Casa Blanca lies the reward for the long uphill climb: rising 140 feet above the sea, El Morro, short for Fuerte San Felipe del Morro, is a photographer’s dream. Construction of the six-level fort began in 1540, and while it was in active use, attacks from both British and Dutch invaders were successfully resisted. Heading east from El Morro, you’ll come to the Cuartel de Ballajá, once a Spanish military barracks. Its second floor houses the Museum of the Americas, which will eventually trace the development of New World society; currently, it hosts an exhibit of folk art, including a model of a country chapel.

Also to the east is the Plaza del Quinto Centenario (Quincentennial Square), a multilevel plaza featuring a totemic monument symbolic of the island’s 500-year-old history. The upper level of the square offers a view of the seaside Cementario San Juan. The 19th-century cemetery is particularly noteworthy for its elaborate tombstones and the circular neoclassical chapel dedicated to Mary Magdalen. The Plaza de San José lies below the new plaza. A bronze statue of Ponce de León graces the square; it was cast from British cannons melted down after an unsuccessful attempt to conquer the island in 1797. The plaza is skirted by a number of historic buildings.

In 1559, the body of Ponce de León was laid to rest in the Iglesia San José, facing the plaza. The church, a superb example of late-16th-century Gothic architecture, was originally a Dominican chapel and is the second-oldest church in the Western Hemisphere. This was the family church of Ponce de León’s descendants. Also on the plaza is the legacy of Puerto Rico’s greatest musician, the Museo de Pablo Casals. The museum houses an interesting collection of the late maestro’s memorabilia, including manuscripts, photographs and videotapes. The Convento Dominicano, a beautiful example of colonial architecture, is just around the corner from the museum. The convent was built by monks of the Dominican Order in 1523. On the southeast corner of the plaza is the Casa de los Contrafuertes, or House of Buttresses. Dating back to the early 18th century, it is thought to be the oldest private house in San Juan. Today, it is home to the Museum of Latin American Prints, as well as a re-created 19th-century pharmacy.

A brisk walk along Calle Norzagaray leads to Fuerte San Cristóbal, Old San Juan’s other guardian. It rises 150 feet above sea level and covers an area of nearly 27 acres. A strategic masterpiece because the enemy could enter it only after capturing five individual structures, the fortress was completed in 1771. The Teatro Tapia, an elegant 19th-century theater, is located a few blocks away on the Plaza de Colón. One of the oldest theaters in the Western Hemisphere, it was recently renovated and frequently offers ballets, concerts and plays. The plaza, renamed to commemorate the 400th anniversary of Columbus’ arrival on the island, is graced by a 100-year-old statue of the Great Explorer. If you decide to explore outside San Juan, you won’t want to miss the Caribbean National Forest, also known as El Yunque, a 28,000-acre rain forest located in the Luquillo Mountain Range. It is the only tropical rain forest in the U.S. National Forest System. The newly opened El Portal Tropical Rain Forest Center provides educational and recreational programs on the rain forest and the environment.