San Juan, Puerto Rico, is arguably the most cosmopolitan city in the Caribbean. The second-oldest European settlement in the Americas, it is a place where world-class restaurants and luxury hotels compete for space alongside glitzy nightclubs and casinos; where Spanish colonial and neoclassical buildings line cobblestone streets; where shopping beckons spend-happy tourists; where art, music, and dance thrive in its theaters, museums, and festivals; and where you’re never very far from wide strips of sand and surf, ideal for sailing, sunbathing, and swimming.

Situated on the northeastern coast of Puerto Rico, San Juan stretches along 25 miles of coastline and 10 miles inland. It spans 30,000 acres of coastal plain, encompassing rivers, bays, and lagoons, and is home to 1.1 million residents in the greater San Juan area. Established by Spain as the island’s capital in 1521, the city’s early role as a military stronghold is evident in its 16th- and 17th-century fortresses and a nearly 400-year-old city wall erected around the oldest part of the city to protect it from foreign attacks.

The heart of the city is historic Old San Juan, a 45-block grid of blue cobblestone streets lined with pastel 16th–18th-century buildings trimmed with ornamental ironwork and hanging balconies. By day its streets crawl with tourists shopping for souvenirs and designer duds. At night it throbs with locals and tourists alike, both partaking of some of the city’s finest restaurants and nightclubs.

As in any large city, all is not paradise. San Juan is a densely populated metropolis thick with automobile traffic. A heavy cruise-ship trade dumps thousands of tourists in the city several days a week, and the number of trinket shops catering to day-trippers has proliferated. Burger Kings and Pizza Huts are not an uncommon sight. Neither are pockets of poor neighborhoods, some of whose residents contribute to a petty street-crime problem.

But despite its big-city ways, San Juan’s natural beauty is apparent in its miles of sandy beaches, its shady plazas, and its beloved coqui, a tiny tree frog whose “co-QUI” song fills the air. As it’s a commonwealth of the United States, American influence is clearly present, but San Juan proudly maintains its Spanish heritage in its language, its culture, and its customs. And although its future is firmly planted in the 21st century, San Juan’s rich history endures in its carefully preserved architecture, its stately fortresses, and the hearts of its inhabitants.

The Best of San Juan

• Ocean Park Beach
• Castillo de San Felipe del Morro
• Castillo de San Cristóbal
• Museo de Arte de Puerto Rico
• Catedral de San Juan Bautista
• Nuyorican Café