Epic 48 Hours in Old San Juan: The Best Things to Do and See

Old San Juan, Puerto Rico, is without a doubt one of the most picturesque places I’ve visited. The beautiful, colorful buildings, cobblestone streets and great food and drinks makes this the perfect place to spend a few days exploring. Although there is so much more to Puerto Rico than just Old San Juan, if you only have a couple days on the island, this is absolutely where I recommend basing yourself. Ready to plan your trip? Keep reading for your guide to 48 hours in Old San Juan: the best things to do and see! 

Sleep: Hotels and AirBnbs in Old San Juan 

Old San Juan is relatively small, so no matter where you stay you’ll be within walking distance to shops, restaurants and attractions. While I’ve always stayed in AirBnbs in Old San Juan, simply because when I’ve traveled they’ve been more affordable, there are also some great hotel options.

Hotels in Old San Juan: 

• Decanter Hotel
• Navona Studios 
• El Colonial – Adults Only 
• Hotel El Convento
• Villa Herencia Hotel
• Fortel Hostel 

Eats – The Best Restaurants in Old San Juan 

All throughout Old San Juan you’ll find a wide variety of restaurants. You’ll find places that specialize in traditional Puerto Rican food as well as many other types of cuisine. If you can, I recommend making reservations for any restaurant that takes them, as places tend to fill up quickly. 

Coffee 

• Cafe Cuatro Sombras 
• Bien Papayas 
• Don Ruiz

Breakfast + Brunch

• St. Germain
  • They specialize in vegetarian cuisine, but also offer non-veggie options.
• Cafetería Mallorca
  • Traditional Puerto Rican food, the mallorcas are a must-try! 
• Kaffe Haus 
• Chocobar Cortés

Lunch + Dinner

• Stuffed Avocado Shop
  • Very casual, takeaway style. Great for a quick, healthy meal.
• Cafe el Punto
  • Traditional Puerto Rican cuisine. 
• Deaverdura
  • Traditional Caribbean dishes, there will likely be a long line. 
• Bacaro
  • Delicious Italian food, make a reservation.
• Triana Tapas & Flamenco
  • Make a reservation for dinner during the Flamenco show at 7:30pm, more information on their Facebook Page. 
• La Madre
  • Mexican cuisine. 

Dessert

Puerto Rico is known for their delicious paletas (popsicles)  and you can find numerous shops specializing in these treats. There are both water and milk based options, and trying all of the flavors is one of my favorite parts of a trip to Puerto Rico. 

• Señor Paleta
  • The most famous and, arguably, the most delicious popsicles on the island. 
• Zippops Gourmet Paletas
• Limbers
  • $1 each and sold out of a window on Caleta de las Monjas street 
• Anita La Mamma del Gelato
  • Expect a line! 

Food Tours

Old San Juan is also a great place for a food tour! Below are a few options:

• Flavors of Old San Juan Food Tour
• Old San Juan Walk and Taste Tour
• Old San Juan Sunset Walk & Taste Food Tour

Bars

• La Factoría
  • A popular, dimly lit, no-frills bar that plays fun music. La Factoria was ranked #54 on the list of the 50 best bars in the world in 2022, as well as #1 in the Caribbean! 
• Barrachina
  • According to their website, the Piña Colada was invented here, however, there are conflicting reports about where in Puerto Rico it was actually invented and when. Either way, it’s definitely worth grabbing a piña colada at the bar. This is a full service restaurant, so it’s also an option if you’d like to enjoy a full meal. 
• The Mezzanine
  • Try to grab one of the balcony seats at this cocktail bar. 

In addition to visiting the bars on your own, there are also cocktail walks and other fun group activities: 

• Craft Cocktail Walk 
• Sunset Bar Crawl

Activities: The Best Things to Do in Old San Juan

Take a Walking Tour – Or Just Wander the Beautiful Streets

Old San Juan is so beautiful that you can easily spend an entire day wandering around and popping into the shops. I had so much fun walking around San Juan with nowhere to be, just admiring the beautiful buildings, saying hi to the street cats and visiting the shops. 

If you would prefer a guided tour of Old San Juan, where you can learn more about the history of the city, there is a wide variety to choose from. These tours are often just a couple hours long, so they don’t take up too much of your day. 

Walking Tours of Old San Juan:

• Old San Juan Walking Tour
• Sunset Walking Tour in the Historic Old San Juan
• Segway/Scooter Tour

Explore El Morro and Fly Kites

Castillo San Felipe del Morro, often referred to simply as “El Morro,” is the second oldest fort on the island. Construction began in 1539 and it was used as a military fort for hundreds of years in a variety of different capacities. Since 1983, El Morro and the walled city of Old San Juan have been designated UNESCO World Heritage Sites. 

Visitors can tour El Morro and learn about its interesting history. Entrance is $10 for adults, while children under 16 can enter for free. 

If you prefer a guided tour of El Morro, there are also options available: 

• Inside El Morro Castle & Old San Juan Walking Tour
• Explore El Morro Fort: History and Walking Tour of Old San Juan

In front of El Morro you’ll find a huge park space with beautiful ocean views. It’s almost always very windy at the park, making it a great place to fly kites. 

While enjoying the relaxing, expansive lawns, walk down to Cementerio Santa María Magdalena de Pazzi (The Santa María Magdalena de Pazzis Cemetery). This cemetery is one of the most beautiful and unique I’ve ever seen. 

Explore La Perla on a Guided Tour

This recommendation comes with a huge caveat: only go on a guided tour unless you’ve done extensive research and are completely comfortable and informed about going alone. While La Perla is much safer now than 10 years ago, it’s still a place you need to be very careful and mindful when visiting. 

La Perla is a neighborhood in Old San Juan outside of the walled city. Until recently, it was known for being one of the most dangerous neighborhoods in the world, and was largely neglected by the government. Recently, La Perla has begun to morph into a more common tourist destination and crime rates have dropped substantially. However, many locals will warn tourists to stay away from La Perla, despite these improvements. 

Touring La Perla with a tour guide is a great option for tourists who want to learn more about the area’s history, culture and reality. I went on a tour with Carolina from “La Perla Like a Local” and it was such a wonderful, informative tour. I felt completely comfortable the entire time. Everyone we met was so welcoming and kind, and it was a great experience. Carolina knows so many residents of La Perla and with her guidance we came to know and appreciate the beautiful neighborhood. 

Carolina showed us where it was “safe” to visit in La Perla, the malecon area with bars, and where we should avoid. She also told us where we could take photos and where photography should be completely avoided. This is one of the most important pieces of advice you can have when visiting La Perla. Be incredibly cautious and respectful when taking photos. Do not take photos of residents or of their homes. 

I don’t include this information to scare tourists or to make anyone feel uncomfortable visiting La Perla, as it is an incredibly beautiful and unique place to visit. Instead, I intend for this information to help travelers visit in a safe and respectful way. 

Book Carolina’s tour here!

Walk Along Paseo Puerta de Tierra and Explore the Beaches

Although right in Old San Juan you won’t find beaches, there are a few beautiful beaches within walking distance (15-25 minutes). You can easily spend an entire day beach hopping in the area. Starting in Old San Juan and walking along the beautiful Paseo Puerta de Tierra ocean walk, the first beach you’ll come to is Playa del Capitolio. Surprise, surprise it’s right in front of the Capitol Building. 

Playa del Capitolio

You’ll find the stairs down to this little beach right in front of the beautiful Capitol Building. This beach is usually quiet and it’s known for its seaglass. This is a great place to take a beach walk while searching for sea glass and enjoying the scenery. 

Although I was told not to swim at this beach due to the strong rip currents, there were children and adults swimming in the waves. If you choose to swim, be very careful. 

Playa Puerta de Tierra

From Playa del Capitolio, keep walking along Paseo Puerta de Tierra and in about 10 minutes you’ll find Playa Puerta de Tierra. This beach usually isn’t too crowded and it’s a nice place to relax. 

Note: in my experience, Playa del Capitolio and Playa Puerta de Tierra don’t show up on Apple Maps. You can easily find them while walking along Paseo Puerta de Tierra, or search for them in Google Maps to locate the entrances. 

Balneario del Escambrón (Escambron Beach)

Just beyond Playa Puerta de Tierra you’ll find Balneario del Escambrón. This beach and park area is the largest and most visited of the beaches near Old San Juan. There’s a parking area, bathrooms, places to rent snorkeling equipment and stands selling food and drinks. You’ll also find Fortín del Escambrón (a small fort), that offers pretty views and is nice to check out.

This beach is definitely my favorite of the three. However, because of the amenities and size, it will be more crowded. 

From Balneario del Escambrón, you can take the 25 minute walk back to Old San Juan or hop in a quick Uber. 

Take an Art Class

Whenever I travel I’m a huge fan of taking art classes. Am I a very good artist? No way. But I still think it’s a ton of fun and a great way to meet locals. In Old San Juan there are a few great options. 

Through San Juan Sip and Paint you can take painting classes and candle making classes. They also have kite making classes offered occasionally – perfect for flying at El Morro. I had so much fun at the Sip and Paint, and my painting turned out kind of cute! 

Another option is to take a “Make Your Own Traditional Espadrilles” class. Espadrilles are a type of traditional Spanish shoes – but you can now find them all over the world. Making a cute pair of shoes is definitely a fun and unique activity! 

Other Tours and Activities to Check Out

If you have more time in Old San Juan, there are a wide variety of other tours and activities to check out. Below are a few that look like a lot of fun:

• Old San Juan Murder Mystery Tour
  • Or check out Escape Room Puerto Rico
• Old San Juan Harbor Sailing Tour
• Instagrammable Places in Old San Juan

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Old San Juan is the perfect place to spend a couple days exploring. It’s picturesque, walkable and welcoming. I hope you enjoyed my recommendations for 48 Hours in Old San Juan: the best things to do and see. If you have any questions, or anything to add to this post, let me know in the comments. 

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♡Kate

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