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.
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.
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 48-hour itinerary has everything you need for a memorable weekend—and it’s one you’ll definitely want to bookmark for your trip.
48 hours left
A day of ocean views, historic streets, and iconic sips.
Morning: Breakfast 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.
Note: You do not need to be a hotel guest to enjoy a meal here!
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 in my blog post.
Evening: Oceanfront dinner at Wicked Lily
As the sun begins to set, make your way to Wicked Lily, a beachfront restaurant inside the Tryst Beachfront Hotel that serves up creative Puerto Rican flavors with a side of unbeatable ocean views. Think crab-stuffed tostones, smoky cocktails, and the waves just steps away.
Wicked Lily is that friend who knows how to chill and party. It’s casual but colorful, stylish yet laid-back—the kind of place where one drink easily turns into four (in the best way). The music is always on point, the cocktails are bold and fun, and the fish tacos? A must.
And yes! The DJ at Wicked Lily does take requests! 😉
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.
Pro Tip: La Placita is tourist-heavy and plays mostly American pop and reggaeton, so for a more authentic Puerto Rican vibe with live salsa or bomba, check out smaller local venues.
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. It’s the kind of place you’ll want to linger, but there’s still one more day of island adventure ahead.
Midday: Ocean, pool, or spa time
Since you’re already near El Condado Beach, keep things light and laid-back with some well-earned relaxation. Lounge on the sand with a good book, take a dip in the turquoise water, or stroll along the shore and soak up the sun. Prefer poolside vibes? Head back to your hotel for a swim or grab a cocktail from the bar and unwind in a lounger.
Want to really treat yourself? Book a quick spa treatment nearby—many hotels in Condado offer massages, facials, or beachside wellness services. This is your moment to recharge and snap a few 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, great views, and island vibes that linger long after dinner ends.
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—it’s an unforgettable, only-in-Puerto-Rico experience.
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. The pace is relaxed, guides are super helpful, and it’s beginner-friendly from start to finish. If you want to know exactly what to expect (and get a few insider tips), read this blog for all the glowing details.
