One Day in Old San Juan

One day in Old San Juan is the perfect way to get a taste of what this colorful and vibrant city has to offer.

Since Puerto Rico remains a United States territory, San Juan is actually the oldest city in the United States.

Old San Juan is known for its blue cobblestone streets lined with colorful homes and businesses designed with Spanish colonial style architecture.

This historic center of the city is very walkable, making it easy to explore Old San Juan in one day.

Honestly, there’s so much to do here, I guarantee you’ll have a full day full of unique adventures in Old San Juan.

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Table of Contents

No matter how much time you have, this one day in Old San Juan itinerary will help make the most of your time.

You should plan to do a lot of walking during your visit. Be sure to wear comfortable shoes, especially for walking over the cobblestone.

In this guide to one day in Old San Juan, I’ve included the city’s most popular attractions. This way you won’t feel as though you missed out if you’re only in town for a short time.

You’ll also still have time to visit local restaurants serving authentic Puerto Rican food, which you definitely don’t want to miss.

I definitely recommend getting up early to start your day before the crowds come out. This will give you time to enjoy the city while it’s quiet.

Another popular option is to join a local guided walking tour. This tour will take you to most of the places in this itinerary in just a few hours.

If you prefer to go it alone, use this guide as your own DIY Old San Juan walking tour.

Is is safe to walk around Old San Juan?

As a solo female traveler I personally felt very comfortable walking around Old San Juan. I was in Old San Juan for almost 10 days and walked around in the early morning and late evening and did not experience any issues.

That being said, treat this city as you would anywhere else and exercise caution and common sense. Don’t flash your valuables and try to walk with a friend or two when going out in the evening.

Old San Juan is also very clean and I rarely saw people loitering or just standing around. I found locals to be very friendly as well, so if you ever need assistance, don’t be afraid to ask for help.

One Day in San Juan Puerto Rico

Just below are my recommended spots to see while sightseeing in Old San Juan. These are the must see in San Juan attractions, but only do the things you’re most interested in.

This is your trip, be sure to make it your own. I hope you love spending a day in San Juan as much as I did. Don’t forget to take lots of pictures.

San Juan Gate

San Juan Gate is a beautiful and iconic symbol of the city. The gate was built in 1533 by Spanish explorer Ponce de Leon to protect the city from attack. It stands today as one of the most recognizable structures on the island.

The gate has been fully restored to its original glory with two towers flanking either side of an arched opening. The opening leads into Old San Juan’s cobblestone streets.

San Juan Gate is the perfect stop before heading over to nearby Castillo San Felipe del Morro.

Castillo San Felipe del Morro – El Morro

Castillo San Felipe del Morro (El Morro) is a remarkable 16th century fortification and an important San Juan National Historic Site.

This UNESCO World Heritage Site was built to protect the city from pirate invasions. It has stood guard over the bay for centuries.

Visitors can explore its ramparts, dungeons, barracks and watchtowers. You can also take in breathtaking views of El Morro’s rocky promontory jutting out into the ocean.

Here you can learn about the history of Puerto Rican defense strategies through interactive displays and exhibits at its visitor center.

Before you leave, be sure to head down to the Santa Maria Magdalena cemetery. This is a colonial era cemetery and is the final resting place for many prominent Puerto Ricans.

El Morro is the perfect place to enjoy a sunrise or sunset over the Caribbean and San Juan Bay. It’s also a popular place for locals to come enjoy a picnic or fly a kite on the park’s spacious lawn.

Caficultura

Caficultura is the perfect morning destination for coffee lovers.

Located in the heart of the city, this charming cafe offers an unbeatable selection of locally sourced coffees and espresso drinks. The Caramelao, a perfectly sweet mixture of caramel and vanilla, was my personal favorite.

The atmosphere is cozy and inviting with its rustic decor and comfortable seating. It’s a great spot to relax before heading back out to explore the city.

Caficultura also serves up delicious pastries from local bakeries as well as classic breakfast items like Eggs Benedict and French toast.

Whether you’re looking for your morning pick-me-up or just want to enjoy some quality time over coffee, Caficultura is the perfect choice.

Casa Blanca

Constructed as a fortress by Spanish settlers in 1521 and eventually becoming the home of Ponce de Leon’s family, this historical site is full of heritage and culture.

Visitors can explore its lush gardens and courtyards with their original fountains and sculptures which provide an insight into centuries past.

The building itself has been carefully preserved to maintain its colonial style while also incorporating modern amenities such as air conditioning and Wi-Fi access.

On the interior you’ll find a museum housing 16th and 17th century artifacts.

Statue of Don Ricardo Alegria

Located in the heart of Old San Juan, Puerto Rico is a bronze statue dedicated to Don Ricardo Alegria, an important figure in the island’s history.

The statue stands as a symbol of recognition for his hard work and dedication to preserving Puerto Rican culture and promoting economic development.

It also serves as a reminder that cultural heritage should be respected and celebrated, while recognizing the importance of progress.

Visitors will find this monument inspiring and reflective of what makes Puerto Rico such a unique destination.

You’ll find the statue of Don Ricardo Alegria in a small park overlooking the Caribbean. The statue is located between El Morro and Museum of the Americas.

Callejon de la Puerta Bandera

Callejon de la Puerta Bandera (The Flag Door Alleyway) is a unique and vibrant area of the city.

The alleyway is lined with brightly colored houses and cobblestone streets that give it an old-world charm.

The flag door itself is a popular place for photographers and bloggers looking to get pictures of the city.

Do keep in mind this is a local residential neighborhood. Please be respectful and keep the noise down while visiting Flag Alley.

Also, for full transparency, I have edited and removed a significant amount of graffiti from the door pictured above. Don’t be surprised when you arrive if it looks a little different than what you see pictured here.

Old San Juan Food Tour

If you have the time, I recommend booking a local food tour during your one day in Old San Juan.

Puerto Rican fare is known for its spices and for being incredibly flavorful. Taking advantage of sampling as much as possible while you’re out exploring Old San Juan is a must.

The food tour I booked included a walking tour of Old San Juan. We also got to visit several local restaurants to try traditional Puerto Rican food.

The food tours here in Old San Juan are very popular so I recommend booking early. You can see the many excellent reviews for yourself here.

If you’re traveling solo food tours are a great way to meet other travelers. I take food tours often when traveling solo in big cities, it makes for a fun night out.

Senor Paleta

Paleterías (ice cream parlors) can be found all over the city, offering a refreshing escape from the heat.

On a hot day, or any day really, be sure to stop in to Senor Paleta. They’re a local institution in Old San Juan and you just have to try one during your visit.

They serve all sorts of refreshing flavors of Paletas to enjoy as you walk the colorful streets of the city.

I ordered the Nutella flavor which I absolutely loved. They also had pistachio, mango, coconut and about two dozen others. You won’t be disappointed with your selection, trust me.

Museum of the Americas

Museum of the Americas was an unexpected surprise during my time in Old San Juan.

I had not read much about this museum, but found the exhibits to be all very interesting. I especially liked the Sin Pena Ni Gloria (Without Pain or Glory) exhibit.

A visit to Museum of the Americas is highly recommend if you’re in the area. There is also a fantastic restaurant located in the courtyard on the bottom level.

I recommend ordering the Mofongo, it was delicious and quickly became my favorite authentic Puerto Rican dish.

Admission to the museum is just a few dollars and well worth your time. As an added bonus, they also have excellent air conditioning making the museum a great escape from the Puerto Rico heat on a hot day.

Cathedral of San Juan Bautista

The Cathedral of San Juan Bautista is a stunning example of Spanish colonial architecture.

Built between 1521 and 1540, this majestic cathedral was constructed from blocks of coral stone and limestone. It features an impressive façade with two towers flanking the entrance and six large arches that allow visitors to get a glimpse into its beautiful interior.

Inside, one can find intricate stained glass windows, colorful frescoes, and a grand altar made from Italian marble.

The Cathedral also houses several historical artifacts, including the tomb of explorer Juan Ponce de Leon.

With its rich history and beautiful design, the Cathedral is an essential stop for anyone visiting Puerto Rico.

Castillo San Cristobal

Castillo San Cristobal was a fortress built by the Spanish in 1783 to protect the island from invasion.

The fortification consists of three levels and is considered the largest fortress built in the Americas.

Today, visitors can explore the various levels of the fortress. You can walk through the fortress tunnels, and even see the dungeon where prisoners were held.

This makes for an interesting and quick stop if you have the time. You’ll also get some beautiful views of the surrounding Caribbean from the top level of the fortress.

Castillo San Cristobal is a National Park Service site, so you will be asked to pay a small fee for admission when you arrive.

Caribe Hilton

Okay, so the Caribe Hilton is a little out of the way. However, if you’re looking for a great place to sample one of the island’s famous Pina Coladas, this is the place.

The Caribe Hilton claims to be the place where the Pina Colada was born, and who am I to argue?

That being said, several other establishments on the island also make this claim. Don’t hesitate to try as many Pina Coladas as possible during your visit to Old San Juan.

You’ll want to order your Pina Colada from the lobby bar, not from the pool bar. I tried several during my recent stay at the Caribe Hilton and can confirm they are indeed delicious.

One Day in Old San Juan Travel Tips

To make your one day in Old San Juan trip even easier, I’ve included some helpful travel tips down below.

Be sure to wear comfortable shoes and a sun hat while walking around San Juan. It’s very hot and sunny here, you’ll appreciate the shade on your face.
Carry a reusable bottle of water with you so you don’t get dehydrated.
Start your day at sunrise to get great photos during golden hour and to avoid the crowds.
Check out Calle San Justo for great photo spots.
Keep in mind that cruise ships also visit the city. This may make Old San Juan incredibly busy, making it even more important you get an early start.
For popular day trip options consider visiting Ponce, El Yunque National Forest, or Vieques.
Be mindful of hurricane season which takes place from June to September. The months of August and September offer the greatest rick for hurricanes.
Book your San Juan hotel well in advance. This is a very popular destination and you don’t want your first choice hotel to sell out.
Be prepared to pay more for everything. You are on an island, and islands often come with high prices, this one included. You will pay high prices for hotel rooms here, so this is a great place to use any reward nights or loyalty points you’ve been saving up.

I hope you’ve enjoyed this guide to one day in Old San Juan Puerto Rico. Thanks so much for reading.