The US' Oldest City Is A High-Energy Tropical Paradise With Exceptional Food And Architecture

The United States is an incredible place to travel with varied landscapes, epic national parks, and plenty of lively cities renowned for nightlife – but when it comes to historic architecture it can be a little underwhelming. Compared to other destinations around the globe, the U.S. is a relatively young country. Many of the oldest cities in the United States were founded hundreds if not thousands of years after iconic cities in Europe. San Juan, Puerto Rico, which is a United States territory, is a rare exception with some of the best historic sites. It was founded in 1521– almost 100 years before the English settlers arrived in Virginia. 

San Juan is buzzing and vibrant, with something to entice every type of traveler. Foodies will love the local cuisine, which is a mouthwatering blend of Spanish, African, Indigenous, and American flavors. Those in search of art and culture will be delighted by colorful public art displays and museums. If you'd rather do nothing more than lounge on a beautiful tropical beach with a mojito in hand, San Juan is the answer to your prayers. When you factor in the cobblestone streets, historic military forts, and gorgeous Spanish Colonial architecture, it becomes clear that San Juan is one of the coolest destinations under U.S. jurisdiction. There are dozens of accommodations to choose from around the city including private Airbnbs, luxurious hotels, quaint bed and breakfasts, or affordable hostels depending on your budget and travel style. Make the most of your trip to Puerto Rico and head straight to San Juan where you can experience five centuries of fascinating history and culture.

San Juan is Puerto Rico's capital as well as the largest city on the island. It's one of the best budget-friendly beach destinations in the Caribbean and welcomes over 5 million tourists each year. Most visitors fly into Luis Muñoz Marín International Airport (SJU), which services over 20,000 passengers each day.  Since it's a United States territory, a trip to Puerto Rico doesn't require a passport. The airport is conveniently located just minutes away from many of the city's hot spots. 

Most of the roads in Puerto Rico are easy to navigate and well-maintained, so renting a car is a good option, especially if you plan on exploring the rest of the island outside of San Juan. Economy car rentals cost about $50 per day. If you see cheap prices, double-check the fine print to ensure extra fees won't be tacked on. Keep in mind that if you're staying in the Old San Juan neighborhood there are some super narrow streets and parking can be rather expensive. It's easier to walk to most places.  Most hotels do not include complimentary parking, so be prepared to pay around $25 per day. Uber and taxi services are also available in San Juan. You can easily call a car with the Uber app, or hail a taxi from the street. They're often waiting outside of hotels, and there are fixed taxi prices within tourist areas. You'll need cash to pay for your taxi. The official currency used in Puerto Rico is the U.S. dollar and there are plenty of ATMs scattered around the city where you can take out cash. 

History buffs and lovers of beautiful architecture will adore Old San Juan. The streets are literally paved with history – the beautiful blue cobblestones were made in the furnaces of Spanish ships in the 16th and 17th centuries. The Cathedral of San Juan Bautista, a gorgeous Gothic-style church, was originally constructed in 1521 and rebuilt in the 1540s after suffering damage from a hurricane. It is the second oldest church in the Americas and still holds services throughout the week. 

Two historic fortresses are perched above the sea along the old stone walls that the original Spanish colonizers built. Castillo San Felipe del Morro was built in the 16th century and served to protect the city from military threats coming from the ocean. Castillo San Cristóbal is another military fortress designed to protect the city from military threats coming from the land. Both have been used for various military purposes for hundreds of years and are now UNESCO World Heritage Sites.

San Juan's oldest home has been transformed into a museum with artifacts from the 16th and 17th centuries. Casa Blanca was built in 1521 for the governor, Juan Ponce de León, and is open from Wednesday to Sunday. Other historic landmarks worth checking out include La Fortaleza, originally intended to be a fortress, but over the years it has been used as an arsenal and a prison. Eventually, the structure was transformed into a luxurious governor's palace, and 170 governors of Puerto Rico have lived there since 1846. While it's still in use as a government building, visitors can join a guided walking tour to see the splendid interior.

San Juan has an incredible art scene, so make sure to check out some of the public art displays. As you wander through the streets you'll see incredible murals and mosaics created by local artists. The Museo de Arte de Puerto Rico has 24 galleries containing impressive works by Puerto Rican artists spanning hundreds of years. The permanent collection includes over 250 pieces by more than 150 artists.  The expansive gardens behind the museum are a wonderful place to relax and take a break from the hustle and bustle. The museum is open Wednesday through Sunday. Double check opening hours as they vary slightly throughout the week. Admission costs $15 per person.

The Museum of Contemporary Art of Puerto Rico was founded in 1984 and features art from the mid-20th century until today created by artists from Puerto Rico, the Caribbean, and Latin America. The building was once a school and was constructed in 1916. Today, former classrooms surrounding the central courtyard serve as art galleries where you can get a taste of current Puerto Rican art. Admission costs $8 per person. 

Teatro Tapia is a beautiful theater constructed in the 1800s and a great place to catch a live performance in San Juan. It's one of the oldest theaters in the country that's still used today. Don't skip a visit to Santurce where local artists have transformed a once-neglected neighborhood into an evolving canvas of colorful murals. 

If you're out and about after dark, it's hard not to experience San Juan's lively nightlife. If you're in Old San Juan, Calle San Sebastian is where the party is at. The entire street is lined with bars and restaurants, and on the weekends the streets are packed with people. La Factoría is one of the most popular spots. It has several bars, each with its own ambiance. Some of the rooms are laid back, while others are thumping with DJ dance music. For a swanky night out head to The Cannon Club, which has Steinway pianos, a decadent dinner menu, and live music every night of the week. 

Serious partiers will love the various nightclubs and music venues scattered around San Juan. Club Brava at Fairmont El San Juan is a popular spot to see and be seen as you dance the night away. La Respuesta is a great place to see local performers in Santurce, and Coca-Cola Music Hall is a great place to catch world-famous acts.  Coliseo de Puerto Rico José Miguel Agrelot is Puerto Rico's premier sports arena, which also often hosts musical performances. The iconic Puerto Rican musician, Bad Bunny, booked a 21-show residency there throughout the summer of 2025.

When it comes to cuisine, there's no shortage of places to choose from. For a fine dining experience head to Marmalade which serves elevated dishes made with fresh local ingredients. El Vino Crudo is an elegant natural wine bar with light bites in Old San Juan. Caficultura has delicious brunch and a variety of rum and coffee cocktails that will give you the strength to sightsee after a night out on Calle San Sebastian.

Skip the all-inclusive resorts and explore the wonderful accommodation options to choose from in San Juan. If you're looking to stay somewhere historic in the heart of Old San Juan, El Convento is an excellent choice. You'll be a few minutes from many of the most popular tourist attractions. Constructed in 1646 as a Roman Catholic Convent, the building is a beautiful example of Spanish Colonial architecture. Simple but elegant rooms feature views of San Juan, while tiled walkways decorated with antiques and rich woodwork overlook a central courtyard with a restaurant. There's even a rooftop pool and hot tub perfect for watching the sunset.

For luxurious beach vibes head to Fairmont El San Juan located in the Isla Verde area. The entire place is a mid-century modern dreamland with rich wooden details, bold colors, and crystal chandeliers. There are four swimming pools, private cabanas, and an expansive stretch of white sand beach perfect for lounging in the sun. You can enjoy gourmet meals at the onsite restaurants –  Crudo serves sushi, and Caña serves elevated Puerto Rican cuisine. You can dine al fresco under a massive tree at the Banyan Tree Grill, or grab fresh fish tacos by the pool for lunch. Enjoy nightly live music at the speakeasy-style cabaret, or dance all night at the lively club. 

Airbnbs and boutique hotels are abundant, but make sure you research the neighborhoods ahead of time to ensure they're walkable and close to things to do. Some of the Airbnbs are located in residential neighborhoods that might not be the right fit for some tourists.