Old San Juan echoes with centuries of history, dating back to the island's discovery by Christopher Columbus in 1493 and the massive 16th-century Spanish forts overlooking the sea.
Today the neighborhood's cobblestone streets pulsate with salsa music and beckon guests with a walkable, chaotic montage of restaurants, shops and clubs amid the Old World architecture. A visit to Old San Juan can be more than just an afternoon's diversion; it's worth considering this extraordinary enclave as a base for your vacation, and as an alternative to a beach resort.
You can walk from one end of Old San Juan to the other in about 15 minutes, passing buildings in every pastel hue imaginable. Make your way to Calle Tetuan and you'll see a house reputed to be among the world's narrowest at about 5 feet wide. Vines with neon-tinged blooms climb over balconies; trees explode in brilliant colors, and from some spots, you can see the turquoise sea.
Accommodations are plentiful and some hotels, including the renowned El Convento, are historic and unmistakably Spanish in style and ambiance. The El Convento site housed a Carmelite convent in the 17th century; it opened as a hotel in 1962, hosting celebrities like Rita Hayworth. At night in the Moorish-inspired courtyards, you'll hear the famous coqui, a native frog whose big whistle contrasts to its tiny body. The sound is two syllables, in a delightful echo of its name. On Sundays, you'll see weddings across the street at the historic San Juan Cathedral. In peak winter season, nightly rates at El Convento run $280-$400 (cheaper in the fall). Less expensive lodging options include Hotel Milano and Casa Blanca Hotel ($100-$200 nightly in winter).
Start your day in Old San Juan with a stroll early in the morning and have breakfast at the hip Aromas high-tech coffee bar, or Manolin, which has been around for over 60 years and has a retro vibe. Manolin has tables in the back and speckled green counters up front with green vinyl swivel stools. Servers sport crisp white shirts monogrammed with "Manolin Old San Juan" and dark trousers. A full breakfast costs less than $4. Another option is to walk over to the main square, the Plaza de Armas, and have a cafe con leche (coffee with steamed milk) and a mallorca, a sweet roll with powdered sugar. Don't miss the ubiquitous Puerto Rican pastry known as quesito, a tube-shaped puff pastry filled with sweet cheese.
The area has a wide array of restaurants but it can be challenging to find one that serves more than mediocre tourist fare. Try Toro Salao, 367 Calle Tetuan, a Spanish-Puerto Rican fusion restaurant with (rare) outdoor seating on a plaza at the southern edge of the old city. Melao is somewhat out of the way along the waterfront near the southern entrance to the old city, Calle del Muelle 100, but is also very good and has outdoor seating. Verde Mesa, 216 Calle Tetuan, a tiny vegetarian restaurant, only serves lunch but is known for fantastic fruit shakes — no small feat in a place where shakes, known as batidas, are a staple. The French restaurant Trois Cent Onze (its French name translates to the numbers in its address, 311 Calle Fortaleza), is expensive but good.
After 10 p.m., the clubs begin to swing. Some places offer an hour's free lesson before the dance floor opens to the general public. The Latin Roots at the port has a live band that plays Latin standards, along with some of the newer salsa hits. The Nuyorican Cafe in the heart of Old San Juan has jazz or fusion earlier in the evening, then switches to salsa. Other clubs offer rock and flamenco.
Although Puerto Rico's reputation for crime is not undeserved, with more than 890 people killed last year in the island's third-worst year for homicides, the tourist thoroughfares of Old San Juan feel relatively safe. Police are stationed on nearly every corner around the clock. Still, the community has been hit hard by the recession and many businesses are shuttered. You will see "se vende," for sale, on nearly every street.
As a U.S. commonwealth, Puerto Rico is an especially easy destination for Americans to navigate. The currency is the U.S. dollar; if you are a U.S. citizen you don't need a passport to visit, and many people speak English, though this is a great place to practice your Spanish. Be aware that the Puerto Rican accent is unusual in the Spanish-speaking world, so don't be surprised, even if you are a Spanish speaker, if the jargon and pronunciation sound different.
Getting around is easy, too. Old San Juan has free trolleys, including a route that goes to the famous El Morro complex of forts. The monuments are operated by the U.S. National Park Service as the San Juan National Historic Site; last year they attracted over a million visitors. They also comprise a UNESCO World Heritage site, designated as a classic example of European military architecture in the New World. The fortifications were built by Spain on a strategic headland to protect the city, bay and Spanish trade routes from attack by European rivals. Exploring the buildings, ramparts and grounds, with their stairways, arches, tunnels, dungeons and spectacular views, makes a wonderful day's outing. Kite-flying on the grounds is a popular pastime.
For faster transportation than the trolley, cabs are readily available and run on a flat rate. The cabbies provide a printed list of the fares; a ride to the beach is about $15. Or for 75 cents, take the city bus — the guagua. It could be slow-going but you'll eventually reach your destination. There are some lovely restaurants right on the beach, including Pamela's at the Numero Uno Guest House in Ocean Park, where you can have a wonderful ceviche with mango while watching kites flying over the palm-fringed beach and swimmers splashing in the surf. As with many other local restaurants, a 15 percent gratuity is included on the bill at Pamela's, so check before you add a tip.
There are plenty of designer outlets in Old San Juan, including brands like Tommy Hilfiger and Ralph Lauren, but the shopping may not be much better than what you would find at your local mall; no high-end Euro imports here, though you will find local artwork in galleries.
About a 10-minute drive from Old San Juan is the Plaza del Mercado de Santurce, known as La Placita, a daytime market. Evenings, late in the week and into the weekends, when the market closes, restaurants and clubs ringing the market open for business. One of the best but a bit hard to find is Jose Enrique, about a block away from the market on Calle Duffaut in a house with no sign. Arrive early; it's small and reservations are not accepted. Dance your dinner off back in the marketplace, where a dance floor is set up and live or recorded music blares until well into the night.