See Colorful Old San Juan in One Day: A Vibrant and Instagrammable Adventure

Welcome to colorful Old San Juan, a captivating destination perfect for a one day trip, where vibrant colors and rich history combine to create a picture-perfect paradise. I recently spent a week here and am so excited to share this Old San Juan itinerary and travel tips with you.

Get ready to explore the most Instagram-worthy spots in colorful Old San Juan, featuring a delightful mix of popular and hidden gems that offer unique photo opportunities.

As you capture your memories, let the enchanting charm of Old San Juan’s architecture and heritage inspire you to appreciate the beauty and history of this Caribbean gem.

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How to Spend One Day in Old San Juan

Visiting Old San Juan in one day is a great chance to enjoy this lovely Caribbean city’s remarkable past and lively culture. Old San Juan became a UNESCO World Heritage site in 1983, and it’s waiting for you to explore it.

A great way to explore Old San Juan is by taking a self-guided walking tour. Use this post to help you navigate the blue cobblestone streets. As you walk, you’ll find amazing colonial architecture, bright, colorful buildings, and important historical landmarks.

Begin at Plaza Colon, then meander through the picturesque streets, stopping at notable sites like San Juan Bautista Cathedral, La Fortaleza, and Paseo de la Princesa, and end with a visit to El Morro.

Alternatively, you can opt for guided walking tours, like this two-hour walking tour with Flavors of San Juan. Knowledgeable local guides will share fascinating stories and insights about the city’s history, culture, and hidden gems.

This guided experience offers a more in-depth understanding of Old San Juan and allows you to connect with fellow travelers while exploring the city’s charm.

Whichever option you choose, a walking tour through Old San Juan is an unforgettable experience that will leave you with a deep appreciation for the beauty and heritage of this enchanting destination.

Brunch in an Old San Juan Coffee Shop

Exploring the city is a delightful culinary adventure, offering a variety of local flavors and charming atmospheres.

Kick off your day with coffee in Old San Juan at one of the many cozy coffee shops like Café Lab or El Café tal de Borikén, both beloved by locals.

The best time to go is in the morning when the smell of fresh coffee fills the air. Make sure to try a cup of Puerto Rican coffee in Old San Juan.

Head to top spots like Caficultura, Kaffe Haus, or Café Mallorca for a delicious brunch in Old San Juan, each offering a unique experience.

Caficultura is known for its delicious French toast and breakfast skillets, while Kaffe Haus provides a laid-back atmosphere with various sandwiches and omelets.

Café Mallorca is a budget-friendly option famous for its authentic Puerto Rican food, like the Mallorca sandwiches – sweet, fluffy bread filled with ham, cheese, and a dusting of powdered sugar.

These brunch spots are all within a short distance of each other and close to Plaza Colon. Here you will find the “I love SJ” art installation for your first picture of the day.

Old San Juan Self-Guided Walking Tour

Now that you are fueled and ready to go let’s start the day by finding the must-see spots in Old San Juan.

These places are all within walking distance of the San Juan cruise ship port. If you want to explore on your own, it is totally possible and safe to wander the streets of Old San Juan, especially if you are limited on time.

Due to the cobblestone streets, you will want to wear your best walking shoes. Because of the heat, opt for breathable sandals with athletic soles. Here is an excellent choice from Amazon.

Old San Juan is brimming with remarkable attractions and historical sites you can’t miss.

Here’s my curated list of must-see Old San Juan spots and practical advice to make your visit as smooth and enjoyable as possible.

Begin at Plaza Colon

After breakfast, leave Plaza Colon and head west on Calle de San Francisco. You will pass many souvenir shops, restaurants, and coffee shops on your left.

The first plaza on your right is home to Parroquia San Francisco de Asis.

Parroquia San Francisco de Asis, a historic Catholic church from 1756, sits in the heart of Old San Juan. Though it appears modest outside, it’s a beautiful, peaceful place inside. Filled with art, artifacts, and a hidden catacomb, it also boasts the earliest stained glass art in Puerto Rico. This charming church offers a perfect blend of history and picture-worthy moments.

As you walk, you may notice the colorful buildings, all of which have balconies to take advantage of the breezes coming from the Atlantic Ocean.

The original Old San Juan buildings were initially covered in white limewash. The Institute of Puerto Rican Cultural must now approve the buildings’ colors and other architectural details to help maintain Old San Juan’s historic charm.

After leaving the Catholic Church, continue west on Calle de San Francisco. You will see one of three universities in Old San Juan, Carlos Albizu Universidad. This university was established in 1966. It excels in offering degrees in psychology and is the first Hispanic college in Puerto Rico to be accredited by the American Psychological Association.

As you look around this plaza, you will also find Mercado La Carreta, one of the best restaurants and bars in Puerto Rico. While in Puerto Rico, you must try Medalla, Puerto Rican beer, and Puerto Rican fare like mofongo or alcapurillas.

Quick Stop for Old San Juan Desserts Along the Way

Continue west on Calle de San Francisco. You’ll pass another excellent spot for brunch in Old San Juan, Chocobar Cortés. This restaurant serves breakfast and brunch, where every dish uses chocolate in some way. Can you think of a better restaurant concept?

While my mind is on chocolate, just around the corner, north on Calle de la Cruz, you will find Drunken Cookies. Their motto, “Get chip faced in Puerto Rico,” sets the tone for what you will find at this Old San Juan dessert spot.

Order a liquor shot in a glass made of cookie dough! Do you hear me? An edible shot glass!

With flavors like Chocolate Chip Nutella, Chocolate Bacon, Butter Pecan, and Apple Crumble, there has to be one you will love.

After grabbing snacks for the afternoon, head south on Calle de la Cruz, back toward Calle de San Francisco, where you will pass Plaza de Armas.

Plaza de Armas

Plaza de Armas is a special spot in Old San Juan with a rich history from Spanish colonial times. As the main town square, it’s near essential buildings like the town hall and the Department of State.

Enjoy a coffee and dessert on a public bench, and snap a photo with the bronze statue of famous salsa composer Tito Curet Alonso.

Keep heading south on Calle de la Cruz. You should be able to see the Atlantic Ocean as you continue walking.

Follow the street as it curves to the 1938 headquarters of Banco Popular. This eleven-story building is the first skyscraper in the Caribbean.

You’ll notice several things in this area. First, pay attention to the features of the Banco Popular building, where you will see the faces of the Olympian gods on the front.

You will also see a piece of art titled El Girafo by artist Jorge Zeno. There are three of his fantasy animal sculptures throughout Old San Juan.

Take the steps before Banco Popular down to your next stop, Paseo de la Princesa.

Paseo de la Princesa

You must experience the enchanting Paseo de La Princesa, The Princess Promenade. This Old San Juan cherished promenade dates back to 1853.

Just a stone’s throw from the cruise ship port, Paseo de La Princesa is the perfect place to soak up the essence of Puerto Rico during your visit.

You will be treated to many food and drink vendors as you walk along the city walls, with San Juan Bay on one side and the fortification wall on the other.

With its captivating charm, Paseo de La Princesa in Old San Juan is a favorite among locals and visitors alike.

La Rogativa

Walking down Paseo de la Princesa, you’ll see a special statue called La Rogativa.

It shows a group of women holding torches and walking together. This statue represents the women of San Juan who helped protect their city from an attack by the British.

Use the small path called Paseo El Morro to make your way to your next stop.

This beautiful walkway, with many plants and old buildings, has many great places to take pictures and see the ocean, like the San Juan Gate. Once used as a passenger entrance to the city during colonial times, the gate welcomed all to this Catholic city.

Cats, Everywhere

As you walk along this area, you may notice many feral cats.

In historic Old San Juan, the non-profit organization Save A Gato manages a unique cat colony along the Paseo del Morro pathway.

Established in 2004, they’ve successfully reduced the colony’s size by 50% through trap, neuter, and return methods.

Visitors can witness volunteers providing daily care, while some cats are even available for adoption.

Castillo San Felipe del Morro
The Castillo San Felipe del Morro, or “El Morro,” is an iconic 16th-century fortress that proudly overlooks San Juan Bay.

Managed by the National Park Service, this San Juan National Historic Site has a rich history of battles and brave defenders. Once feared by enemies, El Morro welcomes visitors to explore its six levels, learn about its past, and enjoy stunning ocean views.

The breathtaking views alone are worth the visit, but you will also get a fascinating glimpse into Puerto Rico’s history.

A ten-dollar admission fee is good for both El Morro and Castillo San Cristobal in Old San Juan.

From El Morro, head back towards the cruise ship terminal, stopping at another Old San Juan Instagram spot.

Old San Juan Cemetery

Santa María Magdalena de Pazzis Cemetery in Old San Juan is a must-see spot. This beautiful cemetery isn’t just for remembering the past and enjoying amazing views. While exploring Castillo San Felipe del Morro, walk around the cemetery and experience its unique charm.

Old San Juan’s Governor’s Mansion

Once you leave the cemetery, head south on Calle de Cristo.

La Fortaleza, the Governor’s Mansion, is a stunning example of colonial architecture. You can admire from the outside or schedule a guided tour to discover the rich history of this UNESCO World Heritage Site.

As you walk around, be amazed by the mix of European and Caribbean buildings and marvel at the blend of architectural styles.

The historic street leading up to the Governor’s Mansion is Calle de la Fortaleza, also known as Umbrella Street.

Famous for its vibrant umbrella installation, Calle de la Fortaleza is a must-see for a colorful and Instagram-worthy photo opportunity.

When you visit, you may notice a strong police presence and that the street is blocked off.

During the summer of 2019, thousands gathered for nightly protests, which is why it is also called Calle de la Resistencia.

You can still snap photos, but you’ll have to get creative to avoid getting the orange barriers in your shot.

Colorful umbrellas aren’t the only thing you might see when you visit Calle de la Fortaleza. At times, the umbrellas are changed out with other equally impressive displays.

You can find the Anita, La Mamma Del Gelato shop near Calle de la Fortaleza for another afternoon snack idea. You must stop and try one of the many flavors. Don’t be discouraged if there is a line. It is worth the wait.

Cathedral of San Juan Bautista
Steps away from Calle de la Fortaleza, you will find 500 years of history at Catedral San Juan Bautista, the heart of Old San Juan’s religious heritage.

When you visit Puerto Rico’s oldest and second oldest church in America, embrace peacefulness.

The stunning architecture and sacred atmosphere provide a captivating backdrop for your photos, inspiring you to appreciate the beauty and history of this remarkable landmark.

This beautiful cathedral is the final resting place of Ponce de León and a testament to the city’s rich religious history.

When visiting, please dress modestly and maintain a respectful atmosphere.

Keep heading south on Calle del Cristo to Capilla del Cristo, making stops at any of the shops along the way to pick up Old San Juan souvenirs, which are surprisingly inexpensive.

Capilla del Cristo

The Capilla del Cristo, a charming 18th-century chapel, is a must-see in Old San Juan. The Spanish Baroque-style structure features a curved belfry and stunning silver and gold altar at the end of Calle del Cristo.

The legend is told that a young rider and horse could not stop and tumbled over the wall during a horse race down the street. People say a miracle saved him, so they built this chapel where it happened.

After admiring the chapel, take the small pathway to the left of the chapel, which will lead you toward Calle Tetuán, a cobblestone roadway. On your way, you will pass Parque de las Palomas, Pigeon Park.

Pigeon Park, or Parque de las Palomas, is a small, peaceful spot in Old San Juan. Located near Capilla del Cristo, it’s a great place to take a break from all the walking throughout Old San Juan.

You can buy bird food for $1 and feed the friendly pigeons. Enjoy the remarkable trees, interesting wall holes, and pretty views of San Juan Bay.

Look for the tiny house with the yellow door along the way, La Casa Estrecha. This is said to be the narrowest home in North America. The owners actually own the red home to its right as well.

End your day in Old San Juan

As you stroll along Calle Tetuan, take in the beautiful ocean views as you make your way back to the cruise port and main area of town.

Cool off with a stop by Señor Paleta for a refreshing paleta, a traditional Puerto Rican treat. With flavors like Ferrero Rocher, mango, and Nutella, you are sure to find one you love. Of course, I had to try the Pina Colada, and it was delicious.