An Amazing Weekend in Old San Juan

If you have been with us for a while, you already know that I love Puerto Rico.  And while I love the entire island, I am head over heels crazy in love with Old San Juan.  So much so that on my last trip to the island I spent an entire 3 days in Old San Juan without leaving, and there were still more things to do in Old San Juan that I didn’t get to.  It was such a good experience that I knew others would enjoy it too, so I decided to create this weekend in Old San Juan guide.

There is something magical about walled cities that captures the imagination all around the world.  While several cities in the United States had walls at one time, Old San Juan is the only city where they remain. 

Within those walls more than two dozen historical sites still stand, ancient brick streets are lined with pastel townhouses, and European-style plazas are gathering spaces.  A culture of its own thrives, with day-to-day life and business flowing between the history and tourists, where coffee houses and public parks bring people together, and feral cats and pigeons have become part of the community.  With 3 days in Old San Juan, you become a part of this story for a brief moment.

This is not a sun and surf weekend, although we might hit a bit of sand.  If you’re looking for a beach weekend in the Puerto Rico capital the Condado or Isla Verde neighborhoods are the way to go. 

This is also not a hipster style artsy partying weekend, although we may dabble with both.  If that is the weekend you prefer, Santurce is the way to go.  We won’t be looking for exclusive shopping or luxury spa treatments.  Head back to Condado for that. 

We also won’t talk about getting out to explore the island.  Check out our Puerto Rico Road trip if you want to see the island, (we even have a Puerto Rico driving guide to help,) or if you just want a taste, our day trips from San Juan.   And, if you are considering some island hopping, check out our favorite islands in the Caribbean.

Now, the entire island is amazing, which is why we’ve already written about it, and San Juan is a fantastic city.  Someday soon we’ll probaby put together an itinerary guide for the entire city.  But right now we are only talking about a weekend in Old San Juan, one neighborhood in the city that lies on the western half of the Isle of San Juan.  It’s the part of the city where the original Spanish fortifications stood, and its walls still remain.  So yes, we are planning an itinerary for an area of about 17 square blocks, but those 17 blocks pack a punch. 

It’s not just me that thinks so either.  

What is Special About Old San Juan?

The United States National Park Service manages and preserves the two major forts the island, El Morro and the Castillo, and the city walls, along with El Canuelo, a small crossfire fort across the harbor.  

The NPS website says:  “San Juan National Historic Site preserves stories of great ambition and aspirations. Countries fought for control of this tiny yet strategic island for centuries. Generations of soldiers have lived and worked within the forts. Visitors today are as inspired by these stories as they are by the beauty of the architecture and the ingenuity of design and engineering of this World Heritage Site.”

These sites, along with La Fortaleza, former military fort and current Governors Mansion, are recognized by UNESCO as a World Heritage Site for “Outstanding Universal Value.”  Although this thoroughly designed in UNESCO documentation, I think the following paragraph states its value in the simplest terms”

“The varied examples of military architecture from the 16th to 20th centuries in the fortifications of San Juan are evidence of the imperial struggles that defined the development of the Americas. As one of the first as well as one of the last of the numerous seats of power in Spain’s American empire, these structures are now potent symbols of the cultural ties that link the Hispanic world.”

Beyond all of this official recognition, Old San Juan oozes history.  You’ll feel its 500 years all around you, in every step.  But it is also bright, colorful and gorgeous, surrounded by stunning natural scenery, and filled with a kaleidoscope of Caribbean Colonial architecture.  It is lively and effervescent, a real neighborhood and home to friendly and welcoming people who embrace “the good life,” and don’t mind sharing it with you.

Planning your Weekend in Old San Juan

Getting to Old San Juan

Getting to Old San Juan is pretty straightforward, especially if you’re flying into Puerto Rico. Most people will arrive at Luis Muñoz Marín International Airport (SJU), which is the main airport for the island.

From the airport, it’s only about a 20- to 30-minute drive to Old San Juan. You can grab a taxi right outside the terminal—don’t worry, they’re easy to find.  Better yet, they have a government regulated flate fee to Old San Juan.

If you’re renting a car, be prepared for narrow streets and limited parking options in Old San Juan. It’s a compact neighborhood, so once you’re there, you really won’t need a car at all.  This itinerary is set up so that transportation is only needed once.

If you’re coming from elsewhere in San Juan, like the Condado or Isla Verde areas, a quick Uber ride will get you there in no time. And if you’re feeling extra adventurous and want a little more local flavor, the public bus system does have routes that drop you off right near the old city walls. Just keep in mind that the buses aren’t the most reliable in terms of timing.

Where to Stay in Old San Juan

Old San Juan has some beautiful, historic hotels that will make your stay feel like you’re living in a piece of history. You really can’t go wrong with these two standout options:

El Convento

If you want to experience your 3 days in Old San Juan in all its historic glory, El Convento is where to stay. This luxury hotel is housed in a former 17th-century convent and retains much of its colonial charm.

The rooms have that perfect balance of old-world elegance and modern amenities. Plus, the courtyard, with its hanging vines and fountains, feels like a peaceful oasis in the heart of the city. The best part? El Convento is literally across the street from the San Juan Cathedral, so you’re right in the thick of the best historic sites.

La Terraza de San Juan

For something a little more low-key but still stunning, check out La Terraza. This boutique hotel feels more like a home away from home. The rooftop pool offers some of the best views of the city, and the rooms are uniquely decorated with a blend of vintage and contemporary touches.

It’s perfect for travelers who want something a little more relaxed but don’t want to sacrifice charm or comfort. La Terraza also happens to be just a couple of blocks from Plaza de Armas, so you’re never far from the action.

If you’re looking for a couple of other options, Hotel Casablanca offers a funky, artsy vibe, with Moroccan-inspired decor and a rooftop terrace with personal soaking tubs, at a great price. And the Decanter Hotel is another charming option, offering cozy rooms, but a more basic set of amenities.

Your 3 Days in Old San Juan – Day 1

Breakfast at Your Hotel

Before diving into your weekend in Old San Juan, fuel up with breakfast at your hotel. Both El Convento and La Terraza offer great options to start your day.  

El Convento offers breakfast at the Patio del Nispero, where you can sip your coffee surrounded by lush greenery and Old World charm.  The Brioche sandwiches are a savory treat, and the fruit and cream laden French toast is absolutely decadent.

If you’re at La Terraza, the dining area is indoors, and the breakfast menu a little simpler, yet everything is prepared fresh and delicious.  And, they offer Continental breakfast free for up to 2 guests per room.  

Explore El Morro

Start your journey at El Morro, the iconic 16th-century fortress that has guarded the entrance to San Juan Bay for centuries. Fully named Castillo San Felipe del Morro, this was Spain’s first military stronghold built on the island, and one that was considered key to the control of both the island and the Caribbean portion of the Spanish empire.

The engineering and construction of this fort were state of the art in their time, such that they have stood the test of attacks and time. The fort was taken once, in 1598, by the British Navy under Sir George Clifford, but these troops withdrew only six weeks later. Otherwise, El Morro has withstood four additional attacks, including the 1898 bombardment by the US Navy during the Spanish-American War. So well built was El Morro that even in WWII, it was fortified and used as a defensive post against German U-boats.

Today, the fort has been restored to resemble its original state, as a Spanish military fort, for protection against sea attacks. Walk along its massive stone walls and explore the various levels. Take time to read the informational signage to learn the purpose of different parts of the base. While you’re there, you’ll also enjoy the breathtaking views of the Atlantic Ocean from a variety of different vantages. Don’t forget to bring a camera, as the photo opportunities here are endless.

Fly a Kite

If the weather is pleasant, upon your approach to El Morro, you probably saw people flying kites in the long esplanade. This area is freely available for public use, and locals come frequently during leisure time.

Flying kites is one of the most common entertainments on the lawn, as the breeze is almost always perfect for attaining the right loft.

I know it’s surprising, but I have never been toting a kite along when I traveled to Puerto Rico, and equally surprising is the fact that you probably won’t either. But, not to worry. When the weather is right, small vendors often set up tents offering kites for sale on the corners in the area.

It’s a fun and inexpensive way to enjoy a very local experience during your weekend in Old San Juan. When you’re finished, you can give the kite to a nearby family.

Take a Walk Through Cementerio Santa María Magdalena de Pazzis

While you’ve been on the lawn, I am sure you couldn’t help but notice Cementerio Santa María Magdalena de Pazzis, directly across from El Morro. Perhaps it’s a little creepy, but I find it fascinating to walk through cemeteries when traveling.  Often they are filled with stunning art  and small bits of forgotten history, sharing an essence of the community through the manner in which they honor and memorialize their loved ones.  

(We visit cemeteries in our itineraries for New Orleans, Columbia, Savannah, Richmond, San Francisco.)

However upon entering there is a definitive order between both the flourishes, and the ornate and intricate art of mourning and remembrance. Behind it all is the infinite backdrop of sea and sky.

Santa Maria is an interwoven part of San Juan’s history, and some of the island’s most prominent figures are buried here, outside of the city walls. This was for the protection of the people, as although the pre-Colonial Spanish grieved and memorialized their beloved, they feared the dead and the afterlife. They kept their burial places separated from homes and businesses.

The cemetery offers a peaceful and reflective atmosphere, and a beautiful place to more fully understand the history of those who constructed the city we visit today.

Lunch With a View at La Vergüenza

The fried local cheese with guava sauce was fresh and delightful, something completely unexpected. We had fish tacos and shrimp mofongo, which were both savory and delicious, along with the sweet and refreshing Verguenza Colada.

The icing on the cake was being seated on the third-floor balcony, overlooking La Perla and the Atlantic, with the salsa music wafting up from the street below. If I were to spend a weekend in Old San Juan right now, it would be among my first meals on a pretty day.

Wander Through Castillo de San Cristobal

After lunch, make your way to Castillo de San Cristobal, the other portion of the National Historic Site.  It is included with the ticket you already purchased at El Morro. It is the largest fortress ever built by the Spanish in the New World, although you really can’t tell that it is the bigger until you enter.

While El Morro was designed to defend the city from sea attacks, San Cristobal was built to protect against land attack, so its defensive weopons were pointed inland.

It seems so counterintuitive, with its guns pointed outward and the sea at its back.  But there was purpose.  

San Cristobal has a maze of tunnels, dungeons, and massive outer walls.  There are five separate but connected sections of the fort, so how much time you spend here really comes down to how much you wish to explore. 

It also includes the enigmatic and intriguing La Garita del Diablo, the Devil’s sentry box, surrounded by legends.

The views from San Cristobal are just as stunning as El Morro’s, but in a different way. The vibe here is a lot less tourist-heavy, which I always appreciate. Make sure to check out the small museum with exhibits on the fort’s construction and history. 

Spending time at both forts during your weekend in Puerto Rico gives a more varied perspective of the complex history.

People Watch at Plaza Colón

If your 3 days in Old San Juan coordinate with cruise ship days, local artisans set up a small craft market here, so if you’re lucky, you can pick up some unique handmade souvenirs. It is also the starting point for many of the day tours departing from Old San Juan, and different tour groups have their meet-up points on the different corners and sections of the plaza.  People are coming and going through the square all through the day.

Although not its original location, you’ll find the iconic “I ❤️ SJ” sculpture on the north side of Plaza Colón.  Make sure to stop and get your Instagram photo here. 

Learn Maritime History at Museo del Mar

For those interested in sea travel and the waters of the world this should be an automatic, but ship models, artifacts and dioramas always have an element of fascination to them, and the strange navigational tools have sort of a steampunk feeling.  

You’ll also get to see the Guiness World Record holding largest lifesaver collection in the world, including lifesavers from ships all over the world.  Not only is it interesting to read where all of them came from, it makes fun photos.  And, there is also a scale model of the USS San Juan, an Atlanta class light cruiser that saw 4 years of battle during WWII, along with one of its battle torn flags.

Savor Local Fine Dining at Marmalade

Marmalade is known for its creative, globally inspired cuisine and extensive wine list.  It has an intimate and air atmosphere.  The service is attentive and professional, well versed in the menu offerings, and the food presentation executed as an art.

I highly recommend starting with the ceviche—it’s fresh, bright, and delicious. For the main course, I opted for the sea bass, which was cooked to perfection, while my friend had the halibut. We didn’t try the cocktails, but they were stunning to look at as they passed by.  Be prepared for a slightly higher price tag, but it’s absolutely worth it for the quality and experience.

Toast Your Trip with a Night Cap

• Los 3 Cuernos: This casual bar is known for it’s one dollar bill “wall paper.”  They offer creative cocktails to refreshing local brews, and you can add your signed dollar to the wall.
• El Batey Bar: For a dive bar experience, this is the place. It’s a little rough around the edges but full of history, with a vibe that brings locals and tourists together.  You don’t have to sign a dollar here, you just sign the walls.

• Scryer Rum Barrelhouse & Rooftop:  If you prefer to stay on the ritzier end of the scale, Scryer offers small-batch pot-distilled rums, crafted into unique and delicious cocktails.  The atmosphere is comfortable with leather sofas and a rooftop lounge filled with plants.
• El Vino Crudo: If you’re more of a wine lover, this intimate wine bar is perfect for winding down. It’s small and cozy, with an excellent selection of wines.  They have a small plates menu, if you prefer it as a dinner option too.

Your 3 Days in Old San Juan – Day 2

Get Sweet for Breakfast at Chocobar Cortez

Chocobar features a full breakfast and lunch menu of ordinary items enhanced with chocolate, that somehow takes them over the top, coffees, cocktails, pastries, and candies.  I ordered the avocado toast, which was perfectly seasoned, and an iced mocha that was rich and chocolatey (as it should be in a place dedicated to chocolate!). Whether you’re a coffee aficionado or just want something light and sweet, Chocobar has you covered.

Take a Walking Tour

Spend the morning and early afternoon exploring the streets of Old San Juan, where you’ll fall in love with the vibrant colonial architecture and visit landmarks like the Cathedral of San Juan Bautista and La Fortaleza.

You’ll likely also come across lots of the Old San Juan cats. They were originally brought on ships by the Spaniards to keep away rodents, and 500 years later they have a thriving community in Old San Juan. Locals have created a little cat park, and several feeding stations throughout the historic city.

If you prefer, join a guided walking tour to learn more about the city’s history, culture, and hidden gems.  There are several companies that offer guided walking tours of Old San Juan, some free.  Most last about 2 hours, and beging near the piers.

In my opinion the better option is walking on your own so you can take your time at different attractions, and spend a few hours.  I suggest starting two blocks down down from El Morro where our day began yesterday, at Museo de San Juan, and winding your way west and south across the island. 

The places that shouldn’t be missed during any weekend in Old San Juan, in my opinion, are listed below in a logical order. As you move from one location to the next, you’ll find hidden alleyways and fun photo ops, so bring your camera!

• Museo de San Juan: Housed in the former San Juan public market building, this museum offers insight into the city’s history.  The art and exhibits give a peek into Puerto Rico’s past and creative spirit, featuring beautiful pieces by native artists. It’s a great way to set the tone for your day of exploration.  Be sure to wander through the small section of single block streets on the land side of the museum to find some of the street art that adorns the Instagram pages of travelers around the world, such as the Puerto Rico flag mural, and others.

• Plaza del Quinto Centenario: In the next block to the left, this striking plaza was built to commemorate the 500th anniversary of Columbus’ arrival in the Americas, on the first voyage.  It is a quick stop along our route.  The large totem pole at its center is a sculpture embossed with fragments of native Taino pottery, in remembrance of the communities lost through the colonization of the Spaniards, and is a popular photo spot.

• Museo de Las Americas: Located inside the historic Cuartel de Ballajá, a former military barracks, this museum showcases the cultural and ethnic history of the Americas, and Puerto Ricos role and relationship within them.  There are permanent and rotating exhibits that dive deep into indigenous communities, Afro-Caribbean history, and the diverse groups that have melded into the Puerto Rican culture of today.

• Casa Blanca: About a block to the south you’ll find the entrance to Casa Blanca, buil as a residence of Puerto Rico’s first governor, Juan Ponce de León. He died on an expedition to Florida and never lived in the house, although his family did, and it was the official Governor’s residence for about 200 years.  Later it housed military offices, and now it isa a museum showcasing the historical lifestyle of the elite where you can tour the home and wander the lush gardens.
• Plazuela La Rogativa: This small square offers sweeping views of the bay and El Morro. There’s a beautiful bronze sculpture that commemorates the city’s successful defense against British forces.  The legen says that on the night of attack, the Bishop led the women of the community through the streets carrying bells and torches, singing hymns, and praying for deliverance.  The British believed the light and commotion was sign of arriving reinforcements, and departed.

• Puerta de San Juan: Once the primary entrance to the walled city, the old gate is an iconic landmark, and stunning photo opportunity.  Walk through it and feel the essences of countless visitors who have passed through the gate for centuries.  Afterwards, if a cool treat is in order, there is often a piragua (Puerto Rican shaved ice) cart at the top of the slope inside the gate, and Limbers de San Juan (a limber is a sort of popsicle in a cup)  is on the corner across from La Rogativa.

• Casa Museo Felisa Rincón de Gautier: This museum celebrates the life and legacy of Felisa Rincón, San Juan’s first female mayor. It’s a small but inspiring stop.

• Catedral de San Juan Bautista: One of the oldest buildings in San Juan, and the oldest Cathedral on US governed soil, this beautiful church has been offering mass since the mid-1500s. It features striking Spanish Colonial architecture and is home to the tomb of Ponce de León.  Definitely a must-see during a weekend in Old San Juan.  There is a small gift shop off to the right of the main entrance where I bought a beautiful rosary for my son. 

• Plaza de Armas:  Once the main town square, Plaza de Armas is still very central to daily business in all of San Juan, with the Puerto Rican Department of State on one end, and City Hall on the side.  This makes it a lively square in the heart of the city, with a stunning fountain, great for people-watching and a quick coffee break if needed. We came through during every one of our 3 days in Old San Juan last time.

• Las Casa Estrecha: The narrowest house in Old San Juan and a cute, quirky stop for a fun photo.
• Parque de las Palomas: Like the cats of San Juan, the Park of the Pigeons is one more display of the kind and gregarious nature of the Puerto Rican people.  The pigeons flock to the park because tiny homes have been cut into the city wall here, and locals and visitors come and feed them every day. 

The chapel was built in commemoration of this miracle, and although services are not held, it is maintained by a group of local volunteers.  Visitors can stop and wonder, or light a candle and pray.

• La Casa del Libro: A tiny museum housing rare books and manuscripts, printing equipment, maps and some art for color. It is worth a quick stop, but to see the truly historic documents an appointment is required. Book lovers will be in heaven..
• La Fortaleza: The governor’s mansion, which is also part of the UNESCO World Heritage Site, sits overlooking the bay. Originally built as another fortress, it now serves as the governor’s mansion. You can take a quick stroll around the grounds and admire its significance and history.  The gardens ar particularly lovely.

Lunch with a Piña Colada at Barrachina

We saw the sign and had to check it out. We were fully drawn in by the beautiful interior courtyard filled with lush greenery. It’s the perfect place to sip on a cold, sweet piña colada and enjoy some traditional Puerto Rican dishes, like mofongo. Even if it’s just for a quick drink and snack, Barrachina is worth a stop.

Get Some Sun and Sand at Balneario del Escambrón

Okay, so we’re cheating here because Balneario del Escambrón isn’t technically in Old San Juan, but it’s close enough that we can squeeze it in. For those of you who can’t imagine visiting Puerto Rico without hitting the beach, this is the spot. It’s a short Uber ride away and worth the small detour if you want some time lounging in the sand.

Escambrón is a small public beach, known for its calm, clean waters that are perfect for swimming. You’ll find public restrooms, lifeguards on duty, and sometimes food trucks nearby offering cold drinks and snacks. There’s plenty of shade if you need to escape the sun, and on a good day, you can rent a beach chair to relax in style.

Try A Bubbly New Favorite for Dinner at Pio Pio

It’s also known for its fresh, vibrant flavors and an eclectic small bites menu that mixes Puerto Rican cuisine with a few modern twists. Expect dishes that feel both familiar and inventive, with some great seafood options. Whether you’re a foodie, love the bubbly, or just looking for something new, this place should hit the spot.

Celebrate the Day and Your Trip

• La Factoria: A hip bar with a speakeasy essence and some of the best cocktails in town.  It is known for its labyrinth like floorplan, with different levels and rooms, each with their own type of music and crowd.  You might recognize it from the music video for “Despacito.”
• El Taverno Lupulo:  El Taverno is known for its wide selection of craft beers, with more than two dozen on tap.  The bar has a lively atmosphere and often features live music.

• Papijoe Shots & Burgers: As the name suggests, Papijoe’s is known for their shots.  In fact they have a shot roulette wheel with 36 different options.  Of course, they also have beer and regular cocktails.

Your 3 Days in Old San Juan – Day 3

Breakfast at a Local Favorite – Cafetería Mallorca

Both were delicious, but let me tell you, the fresh-squeezed orange juice is also a highlight – it was  sunny and delicious.  

Capitolia de Puerto Rico

After breakfast, head over to the Capitolia de Puerto Rico (Puerto Rico’s Capitol Building). For the walkers, it’s just on the other side of the Castillo, along Avenue de la Constitución.  As you approach, be sure to check out the Walkway of the Presidents along the greenway across the street.  It features lifesize statues of every US President that has visited Puerto Rico while in office.  

The beautiful neoclassical Capitol Building  is worth a visit for its stunning architecture and historical significance. Step inside, and you’ll find fascinating exhibits about Puerto Rico’s political history and culture, and a gorgeous interior dome. The building is home to murals and artwork that tell the story of the island’s journey through time.  Guided tours are available, or you can explore on your own.  As with all US government offices, if Congress is in session they can be observed from the upper floors.  

Playa Del Capitolia

Right next to the capitol building, well, across the backside street and down the stairs, you’ll find Playa Del Capitolia—a small but scenic beach, which you may also remember from the video for “Despecito.”  While it’s not the prime beach destination in San Juan, it offers a peaceful, breezy spot to relax for a few minutes, soak up some sunshine, and enjoy the view of the open ocean. 

 To the right is a nice sandy area where you sit and watch the rolling waves off to the side.  The section to the left just past a some of the rocks, is known for its abundance of seaglass.  You may catch some locals taking a break from their day  It’s a nice little gem to stumble upon in the midst of the city’s hustle and bustle!

Puerto Rico National Guard Museum

Once back at the top of the hill, a block to the left, or east, is the Puerto Rico National Guard Museum, housed in the historic San Juan Arsenal. It’s not the typical attraction for a Puerto Rico vacation, even a weekend in Old San Juan.  

The building itself is fascinating, and the museum is a tribute to the military history of the island.   The exhibits, which include uniforms, weapons, and historical artifacts, offers a glimpse into the role Puerto Rico has played in U.S. military campaigns, and provide an interesting layer to the cultural tapestry of Puerto Rico. Even if you’re not a military history buff, it’s a short and worthwhile stop.

Lunch with a View at Ladi’s Place

We started with the grouper tenders and shrimp-stuffed plantains, both of which were fresh and bursting with flavor. For our mains, we couldn’t went with the shrimp tacos – and they did not disappoint. Between the warm sun, cool breeze, and excellent food, this was one of our favorite meals in San Juan.

Souvenir Shopping on Calle San Francisco and Calle Fortaleza

After lunch, we’re heading back to the center of Old San Juan.  You can take a leisurely stroll back on the walkways alongside Avenue Luis Muñoz Rivera if you wish, as it is just under a mile back to Plaza Colón.  Otherwise order an Uber.  We haven’t done any souvenir shopping on our trip, and we better get that in before the end of our weekend in Old San Juan.

You’ll find a charming selection of local shops and boutiques along Calle San Francisco and Calle Fortaleza, perfect for picking up souvenirs. Whether you’re looking for handmade crafts, colorful textiles, or some traditional Puerto Rican spices to take home, these streets have something for everyone. Of course you’ll find several places selling typical shot glasses and keychains too, but I always suggest finding something unique to the location.  

Don’t miss out on the opportunity to stop by some of the small art galleries along this route, where you can find unique pieces by local artists. 

Feel the Breeze on a Sunset Harbor Sail

As the day starts to wind down, direct your path down to the piers of for a sunset harbor sail. No weekend in Old San Juan is complete without getting on the water.

As you walk along the Marina walkway, don’t miss getting your photo with the !Boricua! Sign near pier 1.  Boricua means Puerto Rican by blood or descent. 

The idea of watching the sun set over the water, with El Morro and the city’s colorful skyline silhouetted in the distance, sounds magical.  The truth is, the sun didn’t actually hit the horizon on our sail, but it was still amazing to be out on the water with the wind through our hair, watching the beautiful skyline of Old San Juan pass before us.  

The rum punch flowed freely on our sail, and yes, we may have gotten a little tipsy, but hey, that’s what vacation is all about!  Our fellow sailers were good company, and the crew was welcoming and informative, sharing different bits of information about the harbor, and the different buildings we could see as we moved along.  

The calm breeze and Salsa music, with beautiful scenery and a light-hearted atmosphere made for a perfect, laid-back evening on the water.

Enjoy a Dinner with Ambiance at Princesa – Cocina Cultura

For the final dinner of your 3 days in Old San Juan, treat yourself to a special meal at Princesa – Cocina Cultura. This elegant, open-air restaurant is tucked away in a beautiful, historic setting, and a local favorite for a special meal. Make sure to book a reservation and dress up a little – it’s the perfect place for a more refined dining experience.  

We started with ceviche and fish croquettes, which were light and flavorful. (I can’t ever pass up ceviche!)  For the main course, I couldn’t pass up the rabbit fricassée – I always consider rabbit a treat! My friend had the roasted cod filet, which was cooked to perfection. Every dish was beautifully presented, and the ambiance was unforgettable. I’m already looking forward to dining here again.

An Evening Walk on La Paseo de La Princesa

After dinner, wind down your weekend in Old San Juan with a peaceful walk along the Paseo de La Princesa. This picturesque promenade hugs the city’s ancient walls, alongside the city where you start, and moving off to the waterfront, offering a beautiful view of the harbor. 

As you stroll, you’ll find the Raíces Fountain, where you can take a moment to reflect on your 3 days in Old San Juan.  If you continue along the water, you’ll pass charming statues and lantern-lit pathways that create a romantic, almost otherworldly atmosphere. At the end of the walk, you can enter the city through the gates again, to go to your hotel, or return the way you came. 

It’s the perfect way to end your trip – with the cool evening breeze, the gentle sounds of the water, and the beauty of the city lighting your path.

Alternative Places to Eat during Weekend in Old San Juan

If you’re in the mood to try different places, or can’t get in at our main suggestions, here are some great alternative restaurants in the same general area, for each day of your weekend in Old San Juan:

Breakfast Options

Day 1 – Don Ruiz: Located in Cuartel de Ballajá, across the street from El Morro, Don Ruiz is a cozy spot known for its locally roasted coffee and fresh pastries. Perfect for coffee lovers wanting to start the day with a jolt of caffeine and a light bite.

Day 2 – Spiga: A quaint bakery offering fresh, homemade bread and pastries. Spiga is loved for its relaxed atmosphere and delicious baked goods—perfect for a laid-back breakfast.  This is a good option if you are opting for a guided walking tour, as many of them begin about a block away.  

Day 3 – Kaffe Haus: A hidden gem with a European café vibe, serving classic breakfast dishes with a Puerto Rican twist. The relaxed atmosphere is ideal for a slow morning start, whether you’re just in a coffee mood, or looking for a big hearty meal.

Lunch Options

Day 1 – El Jibarito: A travel guidel favorite, El Jibarito is an excellent place to go for a traditional Puerto Rican lunch. Their mofongo, one of Puerto Rico’s signature dishes, is said to be famous.  It’s a delicious meal made of mashed plantains and topped with meat, seafood, or vegetables.

Day 2 – Caleta Cafe: Across from the Cathedral, this charming café is a great spot to refuel. Known for its coffee and light bites, with flavors from around the world.  I’s a great place to people-watch while enjoying a refreshing salad or sandwich.  Locals frequent the Plaza de la Catedral across the street to read the morning news and chat with friends over coffee.

Day 2 – Cafe Manolin: A local institution, known for hearty Puerto Rican dishes and diner-style charm. The bistec encebollado (steak with onions) is a must-try, and you won’t leave hungry!  If you take the guided tour ending up on the southern side of the island, this Cafe Manolin is probably your best option.

Day 3 – Cafeteria Guardia Nacional: If it’s a rainy day, you can’t get into Ladi’s, or you want to support the local National Guard, the Cafeteria is a simple, no-frills spot with that is a true local spirit.  It’s perfect for a quick and affordable bite. Their sandwiches and fresh juices are highly recommended, and always hit the spot.

Day 3 – Celeste: Specializing in seafood, Celeste is a bright café with a feeling of genuine European dining rooms.  The munu feature Puerto Rican classics prepared with modern techniques and flavorful twists.  

Dinner Options

Day 1 – Bodega Chic: A stylish bistro with a rustic, homey atmosphere, Bodega Chic offers classic dishes with a mix of French and Caribbean flavors. It’s a cozy spot with an excellent service, perfect for a quiet evening out.

Day 2 – Patio del Nispero: Located in the historic El Convento Hotel, this elegant restaurant offers a fine dining experience in a beautiful open courtyard under the shade of a Nispero tree.  It is upscale, so dress accordingly, and make a reservation.

Day 3 – Verde Mesa: One of the restaurants in Old San Juan that is most highly praised by food critics and foodie writers, Verde Mesa is an eco-friendly, farm-to-table restaurant with a focus on fresh, organic ingredients. Their innovative dishes blend Puerto Rican and global flavors in an artistic setting, and the flavors are busting with the freshness.

Day 3 – Carli’s Fine Bistro & Piano:  Seeing a famous musician is probably among your expectations for your 3 days in Old San Juan, but Carli Muñiz, owner of Carli’s, was the pianist for the Beach Boys through the 70s.  Enjoy delicious tapas, a variety of pastas and risottos, and a list or creative specialty cocktails, along with live jazz music, with Carli often on the piano. 

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Shopping in Old San Juan

Local Markets and Unique Shops:

• The Poet’s Passage: A charming spot that offers a unique selection of local art, poetry, and crafts. It’s a great place to find meaningful, one-of-a-kind souvenirs. (Located near Plaza de Armas, perfect for a stop during your walking tour on Day 2.)
• Ole Puerto Rico: Known for its custom-made Panama hats, this shop also offers a variety of other local crafts and accessories. (Found along Calle Fortaleza, ideal for a shopping break on Day 3.)
• Mundo Taino: A small boutique offering handmade jewelry, clothing, and art by Puerto Rican artisans, as well as food and drink products from the local area. It’s perfect for picking up gifts for loved ones back home. (Located on Calle San Francisco, easily accessible during your Day 3 shopping.)

Souvenir Recommendations:

• Handmade Panama hats from Ole Puerto Rico
• Locally made art and poetry from The Poet’s Passage
• Puerto Rican folk art crafts, coffee and liquors from Café Cuatro Sombras
• Locally crafted charms and fine jewelry at Coqui el Original

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Tips for Your Weekend Old San Juan

• Best Times to Visit: The best time to spend a weekend in Old San Juan is from December to April when the weather is cooler and drier. Many festivals and cultural events happen during these months, adding to the vibrancy of the city.  When I visited in mid-November I caught the tail end of a tropical storm.  January and February have been gorgeous!
• Navigating the City: Old San Juan is best explored on foot. The cobblestone streets and narrow lanes make driving difficult, and parking is limited. Comfortable shoes are a must!  Three days in Old San Juan doesn’t give enough time to explore every nook and cranny, but we gave it a good effort, and saw a lot, as you will.

• Safety and Cultural Tips: Old San Juan is generally safe, but as always, be mindful of your surroundings, especially at night. When visiting religious sites, remember to dress modestly.  Locals are extremely friendly and helpful, and greeting with a friendly “Buenos días” or “Buenas tardes” goes a long way, although most in Old San Juan speak English. 

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Sadly, Your Weekend in Old San Juan Must Come to an End

As you wrap up your whirlwind weekend in Old San Juan, you will almost inevitably wish it weren’t over so soon. Leaving is hard, almost as hard as leaving home.  Old San Juan isn’t just a place you visit—it’s a place you feel and live, one that becomes a part of you.

Speaking fancifully and romantically, over these three days, you’ve wandered through centuries-old fortresses, soaked in vibrant street scenes, dined at some of the best local spots, and reveled in the unique culture that makes Old San Juan so special. You’ve flown kites in the breeze, sipped piña coladas in hidden courtyards, and sailed into the harbor with views of ancient walls guarding a city that still beats with life and energy.  This city weaves history and modernity into every experience. Whether you came for the history, the food, or the beautiful views, there’s something magical about these cobblestone streets that stays with you long after you’ve left.

It may be time to go, but rest assured, Old San Juan will welcome you back with open arms when you’re ready to return.

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