Puerto Rico's Oldest District Is A San Juan Gem Where European And Caribbean Charm Collide

The Caribbean Sea is home to a series of islands belonging to different countries that make up this tropical region. Their lively cultures and year-round sunshine make them popular destinations for travelers looking to relax and unwind in pure island bliss. From Jamaica's hidden beach towns to the powder-soft sands of Barbados, these islands offer a blend of natural beauty, rich culture, and opportunities to explore.

Puerto Rico is widely regarded as one of the top travel destinations in the Caribbean, known for its beaches with strong surf, lush tropical rainforests, and the oldest district in its capital, San Juan, where European and Caribbean influences collide. Old San Juan, or Viejo San Juan, sits at the tip of a rocky peninsula on the island's northeastern shore. Centuries of history and culture are visible in its cobblestone streets and colorful buildings, along with vibrant nightlife, a fantastic food and beverage scene, and two 500-year-old war forts to explore. One Tripadvisor reviewer wrote of the area: "A must-see part of San Juan. Definitely check out the old fort, boardwalk, colorful buildings, local restaurants, lounges and clubs ... Loved walking the cobbled streets and the old trees."

Visit in January to experience Viejo San Juan's most famous street festival. Each year, the streets come alive during Fiestas de la Calle San Sebastian, often shortened to "SanSe" by locals. The festival is the city's largest cultural event, drawing hundreds of thousands of people annually to enjoy four days and nights of live music, parades, street performers, food vendors, and local crafters selling their wares.

San Juan is the oldest city in the U.S. and its territories, first established by Spain in 1521 and influenced by European culture for centuries before it was ceded to the United States in 1898. To protect the city, massive stone walls and two major fortifications were erected, beginning in 1539, and still stand today. Visiting the Castillo San Felipe del Morro, often shortened to El Morro, and Castillo San Cristobal is a central part of exploring Old San Juan. Managed by the U.S. National Park Service, you can visit both forts with one entrance fee through the San Juan National Historic Site.

El Morro is an enormous, six-level sandstone fortress with tunnels, ramps, cannons, hidden rooms, a chapel, and the iconic garitas — sentry boxes that look like watchtowers over the ocean. One of them, Garita del Diablo, is linked to a local legend involving a soldier named Sanchez, who reportedly went missing while on duty one night. Old San Juan's second fort, San Cristobal, began construction in 1634. This 27-acre castle was built to defend against enemy invasions and features multiple levels, an intricate tunnel system, holding cells, and sweeping views over the city and Puerto Rico's prettiest coastlines.

For a relaxing stroll through Old San Juan, head to Paseo de la Princesa, which runs along the old city wall and ends at the Fuente Raices, or Roots Fountain. The fountain features bronze figures representing Taino, European, and African traditions, symbolizing the island's cultural heritage. After a meal, visitors can take the free trolley through Old San Juan to save time and steps while enjoying views from their seats.

After a day of exploring, and your appetite kicks in, Old San Juan offers a wide range of places to eat and drink. La Madre on Calle San Francisco is known for fresh, modern Mexican food with a Spanish twist. Try the chorizo tacos and the fresh seafood ceviche, paired with a signature margarita or mojito. Looking for one of San Juan's legendary piña coladas? The city is widely regarded as the birthplace of the drink, and the popular bar Barrachina on Fortaleza Street is one of the places that claim to serve the original version.

For a distinctive fine-dining experience, Marmalade Restaurant & Wine Bar on Calle de la Fortaleza is frequently ranked among San Juan's best restaurants on Tripadvisor. Its tasting menus change regularly and feature dishes inspired by Afro-Caribbean and Spanish traditions, with ingredients from both land and sea. Desserts include interesting takes on classics, such as the Choco-L8, which incorporates eight varieties of local chocolate.

To get to Old San Juan, fly into Luis Munoz Marin International Airport (SJU) — a jewel of the Caribbean with high scores in friendliness — which offers daily flights from U.S. cities on more than 20 major airlines. From there, take a taxi, bus, or rideshare to Old San Juan. Lodging in San Juan ranges from historic hotels (think $200 to $300 per night) to more affordable short-term rentals. Neighborhoods like Condado and Miramar offer options within a short drive of Old San Juan, often at lower nightly rates (closer to $120 to $180 per night) than properties inside the historic district.