A Perfect Weekend in San Juan, Puerto Rico: What to See, Eat & Do in 48 Hours
Only have a weekend in San Juan? This 48-hour itinerary covers the best things to do, eat, and see—perfect for a quick but unforgettable Puerto Rico getaway.
Two days might not be enough to see it all, but it’s plenty for a short-but-amazing getaway in San Juan.
San Juan in 48 hours? Is it doable? In my opinion, it is absolutely is! While two days may not be enough to see everything this vibrant city has to offer, it’s more than enough for a short-but-amazing getaway in Puerto Rico’s capital. This 48-hour itinerary is perfect for travelers who want to soak up some sun at the beach, eat great food, experience the local culture, and maybe squeeze in an excursion or two.
Short on time? San Juan doesn’t need long to leave a big impression.
Because let’s be real—it’s not about how long you stay, but how much you make of the time you have. New to San Juan or just popping back in? Either way, this weekend itinerary will help you make the most of every minute—and you’ll definitely want to bookmark it for your trip.
48 Hours Left
A day of ocean views, historic streets, and iconic sips.
Morning: Brunch at La Sierña Oceanfront – Courtyard Isla Verde
Begin your day with breathtaking ocean views at La Sirena – a gorgeous oceanfront spot located at the Courtyard by Marriott Isla Verde Beach Resort. Enjoy a tropical breakfast in a relaxed, beachside setting–perfect for easing into island time.
Midday: Wander through Old San Juan
Did you even visit San Juan if you didn’t stroll the colorful cobblestone streets of Old San Juan? This historic district is famous for a reason—it’s a UNESCO World Heritage site that feels like stepping back in time.
With vibrant pastel buildings, centuries-old forts like Castillo San Felipe del Morro, and charming local boutiques and art galleries, there’s so much to explore. It’s the perfect way to soak in the culture, snap some unforgettable photos, and truly get a feel for the heart of the city on your first day.
Afternoon: Piña Coladas at the source
By now, you’ve earned a drink—and what better place to toast your trip than Barrachina, the birthplace of the piña colada? Tucked into a vibrant courtyard in Old San Juan, this colorful spot is where Puerto Rico’s iconic national cocktail was first created.
It’s bright, lively, and often features live music, making it the perfect place to sip, savor, and soak up the vibes—plus, they serve delicious Puerto Rican cuisine too. Creamy, tropical, and absolutely essential, the original piña colada hits different when you’re sipping it at the source. Curious about how this famous drink came to be? Read the origin story of the piña colada here.
Evening: Oceanfront dinner at Wicked Lily
Kick off your night with dinner and drinks at Wicked Lily, a beachside spot that totally nails that chill-but-lively vibe. It’s casual and colorful, with just the right amount of edge.
Snag a seat by the water and settle in for bold cocktails, killer views, and a soundtrack that keeps the energy up all night. The fish tacos are non-negotiable, the truffle fries are a crowd favorite, and their cocktails are strong, fun, and dangerously good. Try the Wicked Mule or let the bartender surprise you.
Oh—and if you’re feeling the music, good news: the DJ takes requests, so you can add your favorite song to the mix while sipping and snacking seaside.
Night: Music & mojitos at La Placita
If you’re looking for nightlife in San Juan, La Placita de Santurce is the go-to spot. What starts as a quiet neighborhood plaza by day transforms into a full-on block party after dark, with bars on every corner, music spilling into the streets, and crowds ready to dance the night away.
It’s where most tourists head in the evenings for drinks, dancing, and a lively atmosphere that’s hard to resist. Grab a mojito, dance to the beat (or just people-watch), and soak up the electric energy of this buzzing hotspot.
24 Hours Left
A day full of beach vibes, salsa or bomba moves and magical waters.
Morning: Breakfast at Ola Oceanfront Bistro
Kick off your last day at Ola Ocean Front Bistro, an elegant-yet-relaxed spot located inside the Condado Vanderbilt Hotel. Just steps from the ocean, this breezy restaurant offers panoramic views of the Atlantic and a breakfast menu that blends local Puerto Rican flavors with upscale classics.
Enjoy dishes like coconut French toast with rum caramel, buttermilk pancakes topped with mixed fruits and vanilla whipped cream, and a fresh fruit bowl. For a savory start, try the salmon benedict or the egg whites frittata with goat cheese, arugula, and cherry heirloom tomatoes.
Midday: Ocean, pool, or spa time
Since you’re already near El Condado Beach, this is a great time to slow things down and enjoy some well-earned relaxation. Lounge on the sand with a book, take a dip in the turquoise water, or go for a walk along the shore while soaking up the afternoon sun.
If you’d rather stay poolside, head back to your hotel for a swim or order a cocktail from the bar and unwind in a lounger. For an extra dose of relaxation, book a nearby spa treatment. Many Condado hotels offer massages, facials, and beachside wellness services. It’s a good moment to recharge—and a great time to catch some golden hour beach photos while you’re at it.
Afternoon: Salsa in the park (or on the beach!)
Now that you’re feeling rejuvenated and relaxed, it’s time to get moving—in one of the most fun and cultural ways possible: dancing! Make your last day count by joining a lively salsa or African bomba class, either in the park or right on the beach.
Don’t worry if you’ve got two left feet—there are plenty of beginner-friendly sessions that welcome everyone. We took a salsa class in the park and had an absolute blast! These laid-back sessions are the perfect way to learn a few moves, meet fellow travelers, and connect with the local culture in the most joyful way.
Evening: Dinner with a view at Social, Condado Ocean Club
Tonight, make your way to Social Restaurant at the Condado Ocean Club. With panoramic ocean views and a sleek, coastal-chic vibe, it’s easily one of San Juan’s most photogenic dinner spots. The ambiance is modern and stylish, with floor-to-ceiling windows and a breezy, beachside energy that feels effortlessly upscale.
Sip a glass of wine or a handcrafted cocktail, and try one of their standout dishes like the truffle risotto, crispy fish tacos, or their fresh catch of the day. The menu blends local ingredients with a creative, elevated twist—perfect for a special night out. Toast to your last night in paradise with good food and great views.
Night: Bioluminescent kayaking tour
If you’re up for an adventure, end your weekend with a bioluminescent kayaking tour in Laguna Grande, Fajardo. Paddle through glowing waters lit by microscopic organisms called dinoflagellates—an unforgettable experience that’s definitely a highlight of Puerto Rico’s natural beauty.
Not only is it magical, but it’s also a sneaky way to tone your arms and get some light exercise in before heading home. And don’t worry—you don’t need any kayaking experience to enjoy this tour.
Tours usually last 2 to 3 hours and include all the gear you’ll need, plus a quick safety briefing before you set off. You might even get a chance to spot some local wildlife or take a short nature walk nearby. Evening temps are perfect for a calm paddle under the stars.
If you want to know exactly what to expect, read this blog for all the glowing details.
Need more planning tips for visiting San Juan, check out my Puerto Rico Travel Guide. It’s packed with everything you need to plan the perfect trip—from where to stay to what to do all over the island.
