San Juan, Puerto Rico’s vibrant capital, is a city where centuries of history meet the rhythm of Caribbean life. Founded in 1521, it’s one of the oldest European-established cities in the Americas. Once a strategic Spanish stronghold, San Juan guarded the entrance to the New World with its imposing fortresses and thick city walls. Today, those same cobblestone streets are alive with music, art, and mouth-watering food.
You will likely want at least 2 full days to explore San Juan.
How to get to San Juan
Most travellers arrive in San Juan via Luis Muñoz Marín International Airport (SJU). The airport is located just 15–20 minutes from Old San Juan and Condado. Taxis and rideshares are readily available outside the terminal — costing around $20–25 USD. Some hotels also offer private transfers, which can be convenient if you’re arriving late at night. For a budget-friendly option, local buses run between the airport and parts of San Juan. Though this option is best for those with light luggage and plenty of time.
If you’re already exploring elsewhere in Puerto Rico, you can easily reach San Juan by car or intercity bus. Highways connect it to major towns like Ponce, Arecibo, and Fajardo, and the drives offer scenic glimpses of the island’s mountains and coastline. Car rentals are widely available at the airport and throughout the city if you’re planning to explore beyond San Juan.
Day 1 – Old San Juan
Morning
Start your adventure in Old San Juan, at the Castillo San Cristóbal, an enormous 18th-century fortress built to defend the city from land attacks. The views of the ocean and skyline are spectacular. Next, wander into the historic heart of the city through pastel-coloured streets lined with Spanish colonial buildings. Make sure to stroll down Calle de la Fortaleza. A picture-perfect street famous for its canopy of colourful umbrellas, one of San Juan’s most Instagrammed spots.
As you head west, make a detour down to the scenic Paseo de la Princesa, considered San Juan’s most beautiful promenade. Continue towards the city walls, where you’ll start along Paseo del Morro, a pathway tracing the old city walls under shady trees and vibrant bougainvillea. You’ll pass by various Bastions, which were the lookout points built into the city walls. They offer panoramic views of Old San Juan’s colourful rooftops and the coastline.
On your walk, you might pass through Parque de los Gatos. This park is true to its name, where dozens of cats lounge in the sun. Some of the cats were super interested in attention, while others were, well, cat-like and completely ignored us!
Afternoon
Next, visit the iconic Castillo San Felipe del Morro (El Morro), perched dramatically over the sea. Its ramparts, lighthouse, and open green lawns are postcard-perfect, and it’s easy to spend hours exploring the tunnels and views.
If you like old cemeteries, walk down to the Tumba de Pedro Salinas Cemetery, a serene white marble resting place overlooking the crashing waves.
Before visiting some museums, stop off at St. Germain Café & Bistro for fresh Caribbean-inspired dishes in a cozy, relaxed setting. Or, if you’re in the mood for a drink wander over to Taberna Lúpulo, a local favourite with craft beers and lively atmosphere.
Complete your afternoon with Museo de las Americas and or the Museo de San Juan.
If you are planning to stay in Old San Juan for dinner, head northeast toward the El Malecón area – a waterfront boardwalk with restaurants and bars.
Day 2 – Modern San Juan
Morning
Head to Santurce, San Juan’s edgy art district. Start at the Museo de Arte de Puerto Rico, which beautifully blends traditional works with bold modern art. There is also the Museo de Arte Contemporáneo de Puerto Rico, if that is more your style. Afterward, stroll the Santurce Art Walk, where colourful murals transform the streets into an open-air gallery.
Stop for brunch at Christianson, known for hearty breakfasts and Caribbean-inspired comfort food.
A fun way to get around is with the electric scooters. We easily fit both of us on one.
Afternoon
Unwind at Laguna del Condado, where you can rent a paddleboard or kayak for a peaceful float. Continue to Ocean Park Beach — a local favourite for its relaxed vibe, clear water, and people-watching.
Dinner
Treat yourself to dinner at Cocina 1760, where traditional Puerto Rican dishes meet creative modern flair.
Evening
If you’re in the mood for a night out, Condado is San Juan’s upscale heart. This area is lined with boutique hotels, rooftop bars, and seaside restaurants, offering everything from elegant dining to lively lounges. Walk the Ashford Avenue strip for people-watching, cocktails, and ocean views.
If you are looking for something more local, try a local bar in Santurce for salsa and reggaetón, to live jazz. Or just head to La Placita de Santurce, where the plaza comes alive at night with locals dancing, laughing, and enjoying cold drinks under the stars.
Final Thoughts – San Juan
Two days in San Juan is just enough time to fall in love with the city. Between the pastel streets of Old San Juan, sweeping ocean views, layers of colonial history, and easy access to beaches and rainforest, it offers a rare mix of culture and nature in a compact, walkable package. Whether you’re sipping coffee in a shaded plaza, wandering centuries-old fortifications, or ending the day with sunset over the Atlantic, San Juan is vibrant.
If you’re planning a trip to Puerto Rico, don’t treat San Juan as just a gateway—give it the time it deserves. Save this itinerary for your travels, and let me know in the comments what you’d add or what you’re most excited to see.
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