Top 20 things you simply can’t miss in Old San Juan, Puerto Rico

There is no better place to begin your journey on the Island of Enchantment than Old San Juan. As the historic colonial district of San Juan and a UNESCO World Heritage Site, Old San Juan is also the cultural heart of Puerto Rico. To help you make the most of your visit, I have put together a list of the top 20 things you simply can’t miss in Old San Juan, Puerto Rico.

From charming cobblestone streets and well-preserved pastel-coloured colonial buildings to the largest forts in the Americas, there is plenty to see in this fascinating neighbourhood.

Top 20 things you simply can’t miss in Old San Juan, Puerto Rico

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STROLL THROUGH SAN JUAN’S COBBLESTONE STREETS

Stroll through San Juan’s winding cobblestone streets, made from the ballast stones of Spanish ships.

These charming streets are lined with colourful colonial buildings in shades of blue, yellow, green, red, and pink. You will instantly feel the rich culture and history of the city.

As you wander through Old San Juan, you will come across lively plazas, local vendors selling handmade crafts and snacks, and cosy cafes serving aromatic Puerto Rican coffee.

Old San Juan is a photographer’s paradise so don’t forget to capture the vibrant doors and stunning murals as you explore.

Make sure to visit Calle de la Fortaleza, one of the oldest and most picturesque streets. It is often adorned with interesting art installations.

While you are exploring, pop into the shops for unique souvenirs and local crafts, and make a stop at Barrachina, known as one of the places where the piña colada was invented.

For a sweet treat, indulge in delicious ice creams at Anita Gelato or Zippops.

Barrachina: 104 Calle de la Fortaleza

Anita Gelato: 65 Calle de la Fortaleza

Zippops: 150 Calle de la Fortaleza

VISIT THE SPANISH FORTS

Explore the impressive Spanish fortresses, Castillo San Felipe del Morro (commonly known as El Morro) and Castillo de San Cristobal.

They are the largest Spanish forts in the Americas. Steeped in fascinating history, both forts feature an array of tunnels, ramps, stairways, batteries, magazines, soldiers’ quarters, and turreted sentry posts.

The admission fee covers entry to both fortresses. However, if you’re short on time, you might need to choose just one.

El Morro is often the more popular choice, featuring a large grassy lawn where visitors and locals can relax and fly kites. It’s a great spot to soak up the sun and enjoy the stunning views.

WATCH THE WORLD GO BY IN THE CHARMING PLAZAS

Old San Juan is dotted with enchanting plazas, each offering a unique slice of local life.

Plaza de Armas

Visit the main square in San Juan, Plaza de Armas. There is a lovely fountain there with 100-year-old statues surrounding it. The statues represent one of the four seasons.

Plaza de la Barandilla 

Head to Plaza de la Barandilla, a popular spot for outdoor concerts. You may stop by La Carreta Mercado Local, a cosy restaurant and cocktail bar with a lovely view of the square.

Plaza del Quinto Centenario

Visit Plaza del Quinto Centenario for great views of El Morro and the historic Santa Maria de Pazzis Cemetery.

Built in 1992 to commemorate Columbus’ first voyage to the Americas, the plaza features a 12-meter-tall tower known as El Tótem Telúrico. It symbolises the origin of the New World.

Plazuela de la Rogativa 

Head to Plazuela de la Rogativa to see the spectacular bronze sculpture, La Rogativa. It refers to an event during the 1797 siege of San Juan by British forces.

According to legend, a group of women took to the streets carrying crosses and torches to pray for the city’s protection.

The sight of flickering lights on the shore prevented the British Armada from invading San Juan. Convinced that these lights signalled the arrival of reinforcements, the British decided to withdraw.

Plaza Darsenas

Head to Plaza Darsenas, a small, tree-shaded plaza right on the bay near the beautiful promenade Paseo la Princesa.

Enjoy Puerto Rican food from local food trucks and visit La Casita, a charming restaurant specialising in Puerto Rican rum.

Plaza Colón

Visit Plaza Colón, located right next to San Cristobal Fort. Also known as Columbus Square, it features a statue of Christopher Columbus, erected to commemorate the 400th anniversary of Puerto Rico’s discovery.

Surrounding the square, you will find a variety of cafes, restaurants, and gift shops.

EXPLORE THE MUSEUMS AND GALLERIES OF OLD SAN JUAN

Old San Juan is home to many museums and galleries that showcase Puerto Rican history, art, and culture.

The Museo de las Américas and the Casa Blanca Museum offer fascinating insights into the island’s rich heritage.

Museo de las Américas

The Museo de las Américas is located in the Cuartel de Ballajá, an impressive structure that once housed 1,000 Spanish troops.

The museum offers various exhibitions that explore the history and culture of Puerto Rico and the Americas.

Calle Norzagaray 

Casa Blanca Museum

Once the home of Puerto Rico’s first governor, Juan Ponce de León, the Casa Blanca Museum gives a glimpse into colonial life and the island’s early history. It exhibits artefacts from the 16th and 17th centuries.

1 Calle San Sebastián

VISIT LA FORTALEZA

La Fortaleza is one of San Juan’s most significant historical landmarks. Built in the 16th century, it serves as the official residence of Puerto Rico’s governor.

Guided tours are available, but they are limited to the gardens and the first floor of the building when the government is not in session.

EXPLORE THE CITY WALL

Explore La Muralla, the historic city wall of Old San Juan. Built in the 16th century to protect the city from invaders, this extensive fortification stretches for miles along the coastline. From atop the wall, you can enjoy panoramic views of the Atlantic Ocean.

WALK THROUGH LA PUERTA DE SAN JUAN.

La Puerta de San Juan is an impressive red gate that has been a key entrance to the walled city for centuries.

Back in the day, there were five gates like this, and the huge wooden doors would be locked every night to keep the city safe from intruders.

The gate is famous for its bold colour and is a popular spot for photos. Passing through it takes you to the scenic Paseo de la Princesa, a charming waterfront promenade.

Calle Caleta de San Juan

TAKE A STROLL ALONG PASEO DE LA PRINCESA AND PASEO DEL MORO

Paseo de la Princesa

Paseo de la Princesa is a romantic promenade lined with gardens and beautiful statues.

As you stroll along, you will come across the remnants of La Princesa prison, as well as several restaurants.

The walkway is often bustling with street vendors selling local crafts, piraguas (snow cones), and traditional candies.

At the waterfront end of Paseo de la Princesa, you will find the stunning Fuente Raíces. This impressive fountain was constructed to commemorate the 500th anniversary of the Spanish discovery of the New World.

It features bronze representations of gods and goddesses from Taíno, European, and African cultures.

Paseo del Morro

Paseo del Morro is a scenic pathway that runs along the edge of San Juan Bay, just outside La Muralla.

Lined with trees, public art, and gardens, this path offers breathtaking views of the bay and the ancient fortifications.

Both promenades offer great photo opportunities and are perfect for a sunset stroll.

WANDER THROUGH THE HISTORIC SANTA MARIA MAGDALENA DE PAZZIS CEMETERY

Santa María Magdalena de Pazzis Cemetery is the final resting place for many prominent Puerto Ricans. It was established in 1863.

The cemetery sits on a cliff with stunning views of the Atlantic Ocean and Castillo San Felipe del Morro.

To get there, walk along the old city walls from El Morro fortress and enter through Calle Norzagaray.

ADMIRE THE FACADE OF ANTIGUO CASINO DE PUERTO RICO

The Antiguo Casino de Puerto Rico is located next to Plaza Colón. This beautiful neoclassical building is hard to miss. It is one of the oldest and most stunning buildings in Puerto Rico.

Even though you can’t go inside, the Antiguo Casino’s ornate façade is definitely worth a look from outside. It has impressive ionic columns, intricate mouldings, and elegant balconies.

Constructed in 1917, the building has a fascinating history. During World War II, it was used as an officers’ club for the U.S. Army. Today, it is a vibrant cultural hub, hosting art exhibitions and various events.

TAKE A PANORAMIC PHOTO OF LA PERLA

La Perla is a unique community of colourful homes perched along the rocky coastline, just outside the city walls of Old San Juan.

The pastel-coloured houses stand out beautifully against the rugged landscape.

While La Perla was once off-limits to tourists, it has become more welcoming in recent years.

I walked through the area safely during the day, but I would recommend avoiding it after dark. A guided tour is a great way to explore the area more closely.

Since La Perla is a residential neighbourhood, it is respectful to ask for permission before taking photos. I took some photos with consent while exploring the community, and I also captured some panoramic views from the city walls.

Fun fact: La Perla gained international fame after being featured in the “Despacito” music video by Luis Fonsi and Daddy Yankee.

VISIT HISTORIC CHURCHES

Old San Juan is home to several historic churches that are worth a visit.

The Cathedral of Saint John the Baptist (Catedral de San Juan Bautista), built in 1521, is Puerto Rico’s oldest church and offers a fascinating glimpse into the island’s early religious history.

Another church worth visiting is the San José Church (Iglesia de San José), established in 1532. It features stunning 16th-century Spanish Gothic architecture.

At the end of Cristo Street, you will find the Chapel of Christ (Capilla del Cristo). This charming little church is one of the most photographed spots in Old San Juan.

Even though the chapel is rarely open, you can still peek through the windows to admire the ornate gilded altarpiece inside.

Cathedral of St John the Baptist: 151 Calle del Cristo

San José Church: 197 Calle O'Neill

Chapel of Christ: 1 Calle del Cristo

FEED THE PIGEONS IN THE PARQUE DE LAS PALOMAS

Just steps away from Cristo Chapel and La Puerta de San Juan, you will come across Parque de las Palomas.

This charming little park is famous for its flocks of pigeons—probably more than you have ever seen in one place! Local vendors sell small bags of birdseed, so you can join in the fun and feed them yourself.

PET A CAT AT SAVE A GATO: THE CAT SANCTUARY

If you are a cat lover, make sure to visit Save a Gato, a non-profit cat sanctuary located near the historic El Morro fortress.

Save a Gato cares for the many stray and abandoned cats in the area and works tirelessly to find them loving homes.

You can donate, volunteer, or even adopt a cat. Visiting the sanctuary is a heartwarming experience. It gives you a chance to interact with the cats and support a good cause.

SIP ON PIÑA COLADA

You can’t leave Puerto Rico without trying its iconic drink – the piña colada. This refreshing blend of coconut cream, pineapple juice, white rum, and ice is an island favourite, though its origins are a bit of a mystery.

Three bartenders claim to have invented it – two from the Caribe Hotel and one from Barrachina in Old San Juan. But no matter who really created it, you will want to taste an authentic piña colada while you are in Puerto Rico.

Barrachina is one of the places that proudly claims to be its birthplace, and it is a perfect spot to try it.

If you are up for something adventurous, head to La Factoría. Known for its creative cocktails, this bar is full of hidden surprises, with unmarked doors leading to secret rooms.

Barrachina, 104 C. de la Fortaleza

La Factoria, 148 C. de San Sebastián

DANCE THE NIGHT AWAY

When you are in Old San Juan, why not dive into the lively spirit of the city and hit the dance floor?

Salsa is the lifeblood of Puerto Rican dance culture, but other Latin dances like rumba are also popular, along with traditional Plena and Bomba.

There are plenty of places to join in the fun. Some venues even offer free dance classes, so you can learn the moves before going to the party.

For a genuine salsa vibe, check out Nuyorican Café or Shing-A-Ling inside La Factoría.

If you are into Bomba and Plena, La Vergüenza Puertorrican Chinchorroto is a great venue to try these traditional Puerto Rican dances.

If you are up for a little adventure beyond Old San Juan, head over to La Placita in the Santurce neighbourhood.

By day, La Placita is a lively marketplace, Plaza del Mercado, where locals shop for fresh produce and groceries. But when the sun sets, this historic spot turns into one of the hottest street parties in town.

The area comes alive with music, and its upscale bars, restaurants, and lounges fill up with people ready to party and dance until dawn.

Nuyorican Café: C. San Francisco 312, 
Old San Juan

La Factoria: 148 C. San Sebastián,
Old San Juan 

La Vergüenza Puertorrican Chinchorroto: 
C. Tanca, Old San Juan

La Placita: 1348 C. Jose M. Raffucci, 
Santurce

VISIT THE HAUNTING TAPIA THEATRE, IF YOU DARE!

For a spooky twist on your trip, make sure to visit the Tapia Theatre (Teatro Alejandro Tapia y Rivera). While it is famous for being one of Puerto Rico’s most haunted spots, with rumours of ghostly footsteps and mysterious voices, there is more to this place than just spine-tingling stories.

As the oldest drama theatre in the United States, it holds a significant place in Puerto Rican history and culture.

Teatro Tapia: Calle Fortaleza

ENJOY PUERTO RICAN FESTIVALS

Be sure to check the local calendar while you are in San Juan. Puerto Ricans love to celebrate! One of the most exciting events is the San Sebastian Street Festival, which takes place every January and marks the unofficial end of the world’s longest holiday season.

This multi-day fiesta turns Old San Juan into a lively street party, with live music on every corner and people dancing in the streets.

SNAP A PHOTO AT THE DOORSTEP OF LA CASA ESTRECHA

La Casa Estrecha is one of Old San Juan’s quirkiest attractions. Architect Antonio Alvarez transformed what was once a simple alleyway into a functional two-story house. At just 1.6 metres wide, it is one of the narrowest houses you will ever see.

The bright green door and cheerful yellow façade make it a perfect spot for a fun photo.

La Casa Estrecha: 101 C. Tetuán

EAT LIKE A PUERTO RICAN

Puerto Rico is known for some of the tastiest food in the Caribbean, thanks to its unique blend of Spanish, African, Taino, and North American influences.

The island’s cuisine features dishes that are either slowly stewed or quickly fried.

For breakfast, try a Mallorca at a local cafe or bakery. This sweet bread, which draws inspiration from traditional Spanish bread, is perfectly baked and dusted with powdered sugar. It is often served with cheese or ham.

For lunch or dinner, you can’t go wrong with mofongo. Made from mashed plantains and garlic, it’s typically stuffed with meat or seafood, but you can get a vegetarian option as well.

Another delicious dish is tostones – crispy twice-fried plantains. You should also try pasteles, which are seasoned fillings wrapped in banana leaves and boiled.

For snacks, try various fritters. They are usually stuffed with meat or seafood, but you can find vegetarian fritters too.

For dessert, indulge in tembleque, a rich and creamy coconut pudding, or flan, a smooth and silky caramel custard. Both are perfect ways to end a meal on a sweet note.

The Best Spots for Breakfast and Brunch

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Spiga

If you’re craving freshly baked treats, Spiga is the place to go. Their brioche buns and walnut cookies are fantastic. They also offer sandwiches and salads.

258 Calle de San Justo

Chocobar Cortés

This place is a must-visit for chocolate lovers. You can enjoy hot chocolate, frozen chocolate frappés, or lattes infused with chocolate.

210 Calle de San Francisco

Cafetería Mallorca

This Spanish-styled diner has been serving locals since 1948. It is known for its pastries and mallorcas and is a popular spot, especially on Sunday afternoons.

300 C. de San Francisco

Kaffe Haus

For a brunch that supports local farmers and fishermen, head to Kaffe Haus. They use seasonal produce and sustainably sourced seafood and meats for a fresh and tasty meal.

311 Calle de Tetuan

The Best Spots for Lunch or Dinner

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Deaverdura

Deaverdura is a place to go for a traditional Puerto Rican meal. Their menu changes daily, keeping things fresh and exciting. The sample platter is a crowd favourite because it lets you try a bit of everything. Just a heads-up: there’s usually a long line, so be prepared to wait. It is worth it!

200 Calle Sol

El Jibarito

This spot looks like a traditional country house and serves some of the most authentic Puerto Rican dishes around. Their mofongos, rice and beans, and codfish stew are fantastic.

280 Calle Sol

Barrachina

Known for its delicious food, Barrachina also claims to be the birthplace of piña colada. So, while you’re enjoying their dishes, make sure to sip on this iconic drink.

104 Calle de la Fortaleza

Stuffed Avocado

For a cosy dining experience, head to Stuffed Avocado. They specialise in stuffed avocados, with options like poke tuna or salmon. They also offer a variety of healthy vegetarian and vegan options.

209 Calle de San Francisco

The Best Spots for Gelato

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Señor Paleta

This small artisanal shop serves handmade gelato and sorbet popsicles made with high-quality, natural ingredients. They offer a variety of interesting flavours, such as tamarindo or nutella.

153 Calle Tetuán

Zippops Gourmet Paletas

Zippops is a funky little shop offering a great variety of gourmet popsicles. You can customise them with your favourite toppings, making each one a unique piece of art.

150 Calle De La Fortaleza 

Sweet Hayley’s Ice Cream

Known for its Instagram-worthy gelato presentations, Sweet Hayley’s offers interesting cone flavours like orange creamsicle, lavender, dark chocolate, and midnight vanilla.

366 Calle de San Francisco

If you’re interested in exploring Puerto Rican cuisine further, you might consider booking a guided food tour.

FAST FACTS

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Getting to Old San Juan

Getting to Old San Juan is pretty easy, whether you are flying in or cruising over.

If you are coming by plane, you will land at Luis Muñoz Marín International Airport (SJU), which is only about 11 miles away from Old San Juan. From there, you can take a taxi or hop in an Uber.

If you are arriving by cruise ship, you’re in for a smooth start—San Juan Cruise Port is right at the edge of Old San Juan, so you can step off the ship and start exploring right away.

If you are already in Puerto Rico and driving over, just know that parking can be a bit of a challenge due to the narrow, one-way streets. It’s usually easier to park in a lot and wander around on foot.

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Staying in Old San Juan

There are not many places like Old San Juan where you can wake up in a beautifully restored colonial building with colourful facades and cobblestone streets right outside your window. There are many charming accommodations in the old town that cater to different tastes and budgets.

El Convento

For a touch of luxury, you might decide to stay in the Hotel El Convento. This place used to be a convent, but now it’s a gorgeous boutique hotel with all the modern comforts you could want.

CasaBlanca Hotel

If you’re looking for something a bit more wallet-friendly but still very charming, the CasaBlanca Hotel is a great choice. It has nicely decorated rooms and a beautiful rooftop with stone bathtubs.

Fortaleza Suites

Fortaleza Suites, located on the historic Fortaleza Street and close to many trendy bars and restaurants, offers cosy and elegant rooms with access to a communal kitchen.

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Other neighbourhoods to explore if you have more time in San Juan

If you have more time to explore San Juan, consider venturing beyond Old San Juan to discover other neighbourhoods.

Santurce

One of my personal favourites is Santurce for its artistic spirit and unique character.

Santurce is a must see for art lovers. This lively neighbourhood is well known for its street art, galleries, and a dynamic culinary scene that ranges from local eateries to upscale dining.

It also offers interesting museums and galleries, including the Museum of Art of Puerto Rico and Contemporary Art Museum.

Visit La Placita during the day to enjoy the market and at night to enjoy the best dancing spots in San Juan.

Condado

Condado is very flashy. It is a major tourist destination famous for its luxurious boutiques, trendy shops, chic resort hotels, clubs, and the finest restaurants.

Miramar

Miramar is famous for its Distrito T-Mobile which is an entertainment complex with many restaurants, bars, cinemas, huge video screens, concert venues, and an indoors zip line.

Ocean Park

Ocean Park is primarily a residential area, but you will find some charming bed and breakfast inns that let you walk right to the beach. It is a great spot for water sports like kitesurfing, windsurfing, and snorkeling.

Plus, Ocean Park Beach is a public beach that is easy to access, making it a perfect place to spend a day in the sun.

Puerta de Tierra

Puerta de Tierra is home to several government buildings, including El Capitolio.

It is also where you will find Balneario El Escambrón, the closest beach to Old San Juan.

Isla Verde

Isla Verde is famous for its luxury resorts, casinos, and night clubs. Its swimmable beaches are popular with windsurfers, watercraft riders, and parasailers.

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San Juan Highlights: Best Tours and Experiences

Mixology class at Casa Bacardi

I highly recommend the mixology class at Casa Bacardi. My experience was a perfect blend of fun and learning. You get to roll up your sleeves and craft your own Puerto Rican cocktails, which is a blast!

Plus, our guide was incredibly energetic and really brought the whole experience to life. You can book the tour here.

El Yunque National Rainforest: Tour with Nature walk

If you’re looking for an adventure in nature El Yunque tour is a great choice. It’s a fantastic way to immerse yourself in the beauty of the rainforest while discovering its unique plants and wildlife.

During my tour, we hiked to several breathtaking spots and even enjoyed a refreshing swim in a secluded waterfall. You can book the tour here.

Sofrito Tours

If you’re looking for an authentic way to explore San Juan, check out Sofrito Tours. You can even customise your tour to match your interests.

I recently joined a tour with Laura, the founder, and it was fantastic. We kicked things off in the vibrant Santurce neighbourhood, admiring stunning street art and murals. After that, we enjoyed great coffee and mallorcas at a cosy café.

Our next stop was Vacia Talega Beach in Piñones, which was peaceful and nearly deserted—perfect for relaxing and taking photos. We also tried some delicious fritters from a hidden local spot.

You can book your tour with Sofrito Tours here.

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I hope you found this article helpful. If you’ve been to Puerto Rico, I’d love to hear your thoughts. Please share your experiences in the comments below.