Planning a weekend in San Juan, Puerto Rico? Whether you’re stopping over before exploring the rest of the island or flying in for a quick getaway, San Juan is the perfect mix of history, culture, and Caribbean charm. With its cobblestone streets, brightly painted buildings, delicious food scene, and lively nightlife, this coastal capital packs a lot into just a couple of days.
During my 8-day road trip around Puerto Rico, I spent a couple of fantastic days in San Juan—plenty of time to try authentic Puerto Rican cuisine, visit incredible forts, and even sneak in a little beach time. Plus, San Juan makes an excellent base for easy day trips to El Yunque Rainforest or a glowing bioluminescent bay.
So if you’re wondering how to spend 2 days in San Juan, this weekend itinerary highlights the best things to do, see, and eat—without feeling rushed. Here’s how to make the most of your San Juan weekend trip!
Why Visit San Juan, Puerto Rico for a Weekend?
Many people visit Puerto Rico solely to spend time in San Juan! For starters, it’s incredibly accessible, with both airports and cruise ports making regular stops here. And especially if you don’t have much time to spare, it makes sense to spend it exploring the city.
But beyond convenience, San Juan just has an awesome vibe. While a lot of it is very tourist-oriented (which could be good or bad, depending on your perspective), it is also a treasure trove of history, culture, and fun vibes!
There are tons of historic streets, buildings, and castillos, paired with colorful streets, amazing music, and cultural museums, providing a wide range of activities for all kinds of travelers!
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Day 1 – Exploring Old San Juan
Morning – Colorful Streets
Start your trip by wandering around the beautiful streets of Old San Juan. This entire area is filled with eye-catching Colonial-style architecture, painted with a rainbow of colors, plus cathedrals, shops, and vendors. (If you have a car, I recommend parking at the Ballaja Parking Garage or Estacionamiento La Puntilla. Both are reasonably priced and conveniently located.)
Spend a few hours weaving back and forth along these streets, taking plenty of pictures as you go! Some of the best areas to explore are Calle de la Fortaleza, Plaza Colón, Plaza de Armas, and Paseo de la Princesa. If you go to Plaza Colón, don’t miss a photo op with the I Love SJ sign and the colorful parrots!
Midday – Castillo San Felipe del Morro
At the northwest tip of Old San Juan, you’ll find Castillo San Felipe del Morro, a large Spanish fortress built in the 16th century. This massive fortress was designed to protect the bay from invasion, and did so for many years, even against formidable naval opponents like Sir Francis Drake! Now, it’s a UNESCO World Heritage Site and part of the San Juan National Historic Site. You can visit the fortress and several other notable historic sites in the area for just $10 per person!
If you only visit the Castillo San Felipe del Morro, however, set aside about 2-3 hours to explore its many levels, from the triangle staircases and dungeon-like rooms to the iconic towers and rooftop views!
Afternoon – Local Shops & Cafes
After you’ve explored the Castillo, head back to the streets of Old San Juan, grab an afternoon coffee and a traditional pastry or two to tide you over until dinner. The 24/7 Mavi Old San Juan has great coffee and some neat seating areas upstairs, and Cafe Estaciones has the best pastries, including traditional quesitos and pastelitos. After that, stroll around in search of some souvenirs. There are plenty of shops around with both standard souvenirs and unique items. So whether you want a t-shirt or some locally-made shelf piece, you’ll have lots of options.
Evening – Dinner and Sunset Stroll
When dinner time rolls around, Old San Juan also delivers on fantastic food. As long as you’re here, you have to try some authentic Puerto Rican cuisine! Thankfully, you’ll find no shortage of highly rated local spots with big points for flavor and vibes.
I recommend Juana la Loca on Calle Tetuan–it was such a unique spot, and the food was top-notch! On weekends, they have live music, too, so it’s perfect for some nightlife. The waiter recommended the Montaditos de Alcapurria, Bollitos de Queso, and Truffle Parm Fries, and everything was spot on!
After dinner, head toward the waterfront (Paseo del Morro) for a nighttime stroll. You can see the Puerta de San Juan, La Fortaleza, La Garita del Bastión de San Agustín, and the city all lit up at night. It’s gorgeous, and the area is well-patrolled to create a safe environment.
Day 2 – Beaches, Food & Nightlife
Morning – Breakfast & Coffee in San Juan
On your second day, start off with breakfast at Café con Ron, located on Calle de San Sebastián. Rumor has it that this little cafe is owned by Bad Bunny, making it a great stop for any fans. But even if you’re not into his music, this is a fascinating hole-in-the-wall to check out. It’s quite small with a bar up front and two small seating areas in the back, but they serve up great coffee, and the Mallorca grilled cheese was one of the best things I’ve ever eaten.
Midday – Beach Time or Museums
Depending on how you like to roll, you can spend your afternoon soaking up some of that famous San Juan sunshine or strolling through local museums to dive further into the culture.
If you choose the beach, Isla Verde is a great spot with plenty of space, amenities, and watersport rentals. If you prefer a more upscale feel, try Condado Beach or the nearby Playita del Condado, which is a great spot for families due to the calm waters. And for those seeking a bit of adventure, consider Balneario El Escambrón, which has a coral reef that’s perfect for snorkeling.
Rather stay indoors? You’ll have tons of museum options, too! Consider Museo de las Americas, an art museum located in old army barracks, or Museo de San Juan, a cultural museum dedicated to Puerto Rican art and artifacts! Fellow book nerds will also appreciate La Casa del Libro Museum, a museum dedicated to historic books and documents, dating back to the 15th century!
Afternoon – More Puerto Rican Cuisine & Chill Time
Want to pack in some authentic local flavor during your trip? Consider booking a guided foodie tour through Old San Juan! Available on both Get Your Guide and Viator, these 3-hour tours give you the chance to try lots of local treats as you dive deeper into the history of many notable local buildings.
Not your thing? No worries! Spend some extra time at the beach or hit another museum, but be sure to grab a late lunch (or heavy snack) before your evening starts.
I particularly enjoyed the assorted frituras at Restaurant Barranchina (widely known as the birthplace of the pina colada), and Daniel liked the grilled salmon. But other popular options include La Garita, Casita Miramar, and Santaella.
Pro Tip: If you’ve never used Get Your Guide before, download the app and use my exclusive code CARRIEDAWAYTRAVELS5 to take 5% off your first booking!
Evening – Salsa Dancing Class & Nightlife at La Factoria
For an unforgettable evening, book a sunset salsa dancing class with a local instructor by the water! You can find quite a few options for these on Viator, starting as low as $19 per person! You’ll spend an hour learning the basics of salsa dancing, one of the most popular Spanish dance styles in the world, while you take in stunning views of the local beach.
Once class is over, grab some dinner before you put those newly learned skills to the test with an evening at La Factoria. This unique spot has multiple rooms, each with a unique theme and vibe. The later the night gets, the more rooms open up, so you’ll want to stick around to see it all–not to mention tear it up in the Salsa Room along with everyone else! It is quite a labyrinth, though, so don’t be afraid to explore and try to find all the rooms!
Best Day Trips from San Juan
If you don’t want to spend your time soaking up San Juan’s history, or you have an extra day or two to spare in Puerto Rico, San Juan is also a great home base for some epic day trips!
One of my personal favorites is El Yunque National Forest, a fantastic spot for hiking! Book a guided tour to see the best spots and do fun extras like slide down a waterfall! At just over an hour away, you can easily get there and back to San Juan.
If you’re interested in seeing a bioluminescent bay in person, head over to Fajardo (about 90 minutes away) for a nighttime kayaking tour! These popular tours take you to Laguna Grande, where you can watch the waters glow bluish-green when disturbed.
Another great option in the area is the Luquillo Beach and Kiosks. These 60 beach-front shops offer a huge variety of local food and souvenirs with the most gorgeous ocean backdrop!
Want a full-day adventure? Head into the mountains and spend a day at Toro Verde Adventure Park, where you can take on tons of zipline-style adventures, including a zipline that goes up to 90 mph and the world’s longest zipwire bicycle track!
Where to Stay in San Juan, Puerto Rico
There are so many places to stay in San Juan, depending on your preference for price, amenities, and location. If you’re focusing your attention on Old San Juan, the hotels and resorts are the obvious choice, although the price tags can be fairly high–and most of the money goes back to mainland companies rather than the locals. But you’ll be within walking distance of pretty much anything you want to do.
If you’d prefer something a bit more affordable that also supports the island community, consider booking an Airbnb instead. We did this most nights during our trip (full reviews of all stays coming soon), and it felt a lot more authentic than just staying in a beachside Hilton. It also made it easier for us to park since we had a car for the duration of our trip.
We ended up staying in this adorable room about 12 minutes from Old San Juan. It was on a gated property with a community kitchen and garden, and it felt like a little oasis. The actual suite was adorable, with colorful tiles, a hammock in the entry, cool glasswork blocks, and all the standard amenities. It was perfect for two people, and at $102 per night with taxes, the price was just right, too!
Travel Tips for a Weekend in San Juan
I have a full guide that breaks down what you need to know before traveling to Puerto Rico, which you should definitely check out. But here are a few must-knows for San Juan.
First of all, if you don’t have to rent a car. Don’t. Especially if you’re staying in Old San Juan, you can reach just about everything on foot, and Ubers are readily available for long trips. Parking, however, can be a bit tricky depending on the time of day and season, so it’s easier to go without unless you absolutely need one. In my case, I rented a car for our 8-day road trip and dealt with parking and driving down San Juan’s narrow streets to reach the parking lots and garages. But once we were there, we wanted to walk because it was all so beautiful! Also, many hotels don’t offer parking, so that can complicate things as well.
Second, be sure to dress appropriately. Puerto Rico is a tropical destination, so you’ll want light, breathable clothes. Athleisurewear is a great option, especially if it has moisture-wicking properties. You’ll also want comfy shoes that can handle the cobblestone streets and sidewalks, rather than heels.
Finally, be aware of your belongings and surroundings. If you do have a car, don’t leave anything valuable inside, and keep an eye on your purse, phone, and wallet at all times. An antitheft bag is always a good idea, and don’t flash around a lot of money or expensive items. (Basic travel safety.) You should also do some research before you travel on what areas to avoid. For example, many tourists go to La Perla because it’s colorful and well-known, but the locals will all tell you to stay away because it’s one of the biggest crime hubs on the island.
FAQ – Weekend in San Juan, Puerto Rico
- Is 2 days in San Juan enough? Yes, it is! You can easily experience the best parts of San Juan in just 48 hours, including the colorful streets, history, art, beaches, culture, and food!
- What is San Juan, Puerto Rico, best known for? San Juan is best known for its colorful Old Town, historic forts, beaches, and nightlife.
- Can you walk around Old San Juan? Yes! And you certainly should! Old San Juan is best experienced on foot, so you can take in all the sights, sounds, and smells!
- Do you need a car in San Juan? You do not need a car in San Juan. In fact, if you can help it, try to utilize walking and local transportation to make your life easier.
Final Thoughts on a Weekend in San Juan
San Juan is such a wonderful place to spend a couple of days soaking up the Puerto Rican sunshine and experiencing the culture! With so much to see and do, you can really pack a lot in–or you can just take things slow and spend your days lazing around on the beach. It’s really up to you!
However, if you do have more time to spend in Puerto Rico, I wouldn’t recommend staying in San Juan. Puerto Rico has so much to offer beyond this tourist-centric area, from rainforests and mountains to snorkeling and zip lining! It’s a fantastic place for adventure and nature enthusiasts because there’s just so much to see and do in such a small area. If you’re interested in learning more about it (and potentially copying my 8-day road trip), I have a full guide for you!
Do you have questions or comments? Please leave them below, and I’ll respond as soon as possible! Want to stay in the loop for the rest of my Puerto Rico series and everything to come? Fill out the form to sign up for my free newsletter and get the latest posts delivered straight to your email, along with exclusive deals and savings from time to time!
Thanks so much for stopping by, and I hope you’ll do a bit more exploring here before you leave. Until next time, happy travels!