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Best 1 Day Old San Juan Itinerary | Colorful Puerto Rico

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In need of a great Old San Juan itinerary? Puerto Rico is one of the best places to go to when it comes to price, Caribbean food, and great weather – with Old San Juan being one of the top highlights. While there’s a ton to see in Old San Juan that takes much longer to experience and visit, this article will give you the gist of all the must-do things and must-see places if you only have one day. 

Who this Puerto Rico itinerary guide is perfect for:

  • If you’re on a cruise and only have limited time when docking in Old San Juan for the day. 
  • If you planned to explore Puerto Rico as a whole and rented a car to get around but still want to see a lot of the historic and fun things of Old San Juan.
  • If you’re there for a layover to a different place and only have a few hours.

Note: Everything is in close proximity and easy walking distance in the historic district (Old San Juan), so if you want to change up this day itinerary or go back to something you can easily reach it within 10-15 minutes! If this is your first time going to the capital city of Puerto Rico, consider visiting most places in this guide, if not all.

colonial buildings in old san juanBest Time To Visit Old San Juan, PR

If you’re still planning your visit to Old San Juan, PR, your choice of when to go best will depend on your preferences when traveling. 

The dry season spans from December to April and offers milder temperatures and minimal rainfall, making it ideal for pleasant weather. However, be prepared for larger crowds, as this is the peak tourist season. 

For a less crowded experience with still wonderful weather: consider traveling between April and June, despite it being the rainy season, as rain typically doesn’t persist throughout the day. 

If you’re on a budget: the low season from August to November is your best bet, with lower prices for accommodations, dining, and activities. It’s also an excellent time to plan your San Juan itinerary without the hassle of peak hours and heavy traffic. Nonetheless, keep in mind that this period coincides with hurricane season, so double check the weather conditions before going – make sure to get trip insurance as well, just in case!

1-Day Old San Juan Itinerary

Whether you’ve spent the night before in Old San Juan or you’re just arriving with the sun rising, I suggest starting the day with a quick breakfast. This way, you will start out with energy for the day and won’t feel too dizzy by lunchtime, especially if you’re fighting higher temperatures during the hot season.

Morning: Best Breakfast in Old San Juanplate with two mallorcas and a cup of coffee

While there are many amazing breakfast places, these have been the best ones I’ve tried so far as they’ve never disappointed – especially if you prefer to stick to local places and food. This not only supports the local economy but you also get the real experience while visiting Puerto Rico.

La Mallorca

This cafe is famous for its Mallorcas (hence the name), which is a sweet, fluffy bread that’s dusted with powdered sugar, often filled with ham and cheese, that perfectly combines the Spanish and Caribbean flavors – it’s especially great if you just want to stop by and grab something.

Café Manolín

Café Manolin is another hidden gem in the heart of Old San Juan – it’s a local favorite for traditional Puerto Rican breakfasts. 

I’ve tried Mofongo here and it was reallllllly good!

The best part? The Ingredients are locally sourced, which means they’re fresh and just bursting with flavors. The coffee, a staple of any Puerto Rican breakfast, is rich and aromatic, often cited as some of the best in the area. 

Traditional Puerto Rico Food

Here are some traditional Puerto Rican foods you should try if you get the chance: 

  • Mallorcas
  • Revuelto Manolín
  • Mofongo
  • Arroz con Gandules 
  • Café con Leche
  • Jueyes Desmenuzados
  • Asopao
  • Bistec Encebollado 
  • Bacalaitos
  • Flan de Queso

Morning: Must-Do Tours In Old San Juan

Here are the best tours for the morning in Old San Juan:

Old San Juan Walking Tour – where you get to explore the colorful streets, historic buildings, and major landmarks through a guided walking tour – book here!

Old San Juan Historical Walking Tour – learn about the historical significance of the city and discover long-lost stories – book here!

Castillo San Felipe del Morro and Old San Juan Walking Tour (together – best value!)get a local guide walking you through Puerto Rico’s rich history, culture, and nature as you walk through the colorful streets into the castle. You also get to see San Juan Cathedral, the Governor’s Mansion, and more! Book here!

Stop 1: Visit Castillo De San Cristóbalcastillo de san cristobal in old san juan and la garrita del diablo

Make your way to Castillo San Cristóbal, another impressive fortress with fascinating history and architecture. My favorite part about this fort is the underground tunnels and secret pathways that you can explore – so cool! Who knows? You may just find a treasure hidden centuries ago? 

History of Castillo San Cristóbal

This fort was built in 1634 under Spanish colonial rule to fortify the eastern approach to San Juan. However, over the centuries, Castillo San Cristóbal underwent several expansions and modifications, evolving into one of the largest Spanish military installations in the New World (mind-blowing!). Nonetheless, following the Spanish-American War in 1898, Puerto Rico became a territory of the United States, and the fortress transitioned from a military stronghold to a historic site and tourist attraction.

Stop 2: Discover Calle del Cristo

Next consider making a quick stop at the Calle del Cristo, one of the charming cobblestone streets that are lined with colorful buildings, boutiques, and art galleries. Take in the vibrant atmosphere and perhaps stop for a coffee or a snack at a local café – one of my favorite things to do!

History of Calle del Cristo

As one of the most iconic and historic streets in Old San Juan, it dates back to the city’s colonial era when it served as a vital thoroughfare connecting various parts of the settlement. The street’s name, Calle del Cristo, is believed to have originated from the nearby San Juan Cathedral, officially known as the Cathedral of San Juan Bautista. Legend has it that the street was named after a statue of Christ that was placed near the cathedral’s entrance. Over time, the street became associated with this religious symbol and was named accordingly.

Where To Stay In Old San Juan PR

If you end up deciding that you want to stay longer in Old San Juan, here are my favorite places:

  • Budget ($)Fortaleza Guest House – A budget-friendly guesthouse known for its clean rooms and central location.
  • Best Value ($$) CasaBlanca Hotel – This boutique hotel offers a great mix of value and comfort, with a beautiful rooftop terrace.
  • Luxe ($$$)Hotel El Convento –  A luxury hotel set in a former convent, offering elegant rooms and top-notch amenities.
  • Unique ($-$$$)Villa Herencia –  A beautifully restored historic building with unique decor and a cozy atmosphere turned into one of the most beautiful boutique hotels. 

Stop 3: Explore Plaza de Armaspaseo de la princesa and fuente raices in old san juan puerto rico

Lastly, make a stop at the Plaza de Armas which is the main square of Old San Juan and it’s surrounded by historic buildings, statues, and fountains – so you will likely see it be very lively. 

History of Plaza de Armas

Located in the heart of Old San Juan, it dates back to the early colonial period in the early 16th century, when the plaza served as the central gathering place and administrative hub of the city. It was designed as a military and administrative center, hence its name, which translates to “Military Plaza” in English. The square was strategically located near the waterfront and key government buildings, including the governor’s residence, City Hall, and the residence of the Spanish military commander.

Stop 4: Walk along Paseo de la Princesa

Next, head towards Paseo de la Princesa, a picturesque promenade along the city walls with stunning bay views (especially pretty at sunset!). On weekends, you will often find a sunset market filled with artisanal treasures and fresh street food that’s to die for. Don’t forget to admire the Fountain of the Princess and enjoy the beautiful views!

Tip: Get an afternoon snack at one of the vendors here!

History of Paseo de la Princesa

Finished in the late 19th century, it was designed as a promenade along the city’s historic defensive walls to beautify the area and provide a recreational space for locals and visitors alike. Though it was finished in the late 19th century, its construction actually began in 1797 when King Carlos III of Spain came to visit with his daughter Princess Juana, after which the fountain was named. 

san juan gate in puerto rico with trees behindStop 5: Walk to San Juan Gate

After you have breakfast at either of the two coffee shops, make your way towards the San Juan Gate where you get to watch the beautiful streets with colorful houses of San Juan with great opportunities for pictures! 

History of San Juan Gate

The San Juan Gate was originally part of the massive walls surrounding the entire Old San Juan neighborhood and served as the main entrance to the city by sea. The Spanish built it to protect the city from pirates and other intruders, though, it was mainly also serving as a port for merchants, settlers, and other governors to do business when entering Puerto Rico.

Stop 6: Visit Casa Museo Felisa Rincón de Gautier (Hidden Gem!)

Right next to the San Juan Gate, you can visit the Doña Fela’s house for FREE, who was the first mayor of San Juan from 1946 to 1968 – she was actually also the first female mayor in the entire Western Hemisphere! In this museum, you will find original furniture from her and even her parents’ as this was her actual home for a long time, which includes personal pictures of her, her 70+ fan collection, and so much more – this is absolutely worth visiting!

Why You Should Visit This Museum

Well, for one, it’s free and who doesn’t love history when it doesn’t have a price tag? Second, it gives you a glimpse into San Juan’s history and authentic home, where you will quickly notice its hispanic home layout for air circulation during the high heat. Doña Felisa was way ahead of her time as a woman and was very successful in making foundational impacts on the country as a whole, such as the children’s health for single mothers program that she started.

You will also get to see her 300+ achievements and awards that she collected in her 22-years of reign as well as a painting from the former president JFK, even! Much of what she did for Sun Juan eventually also hit the USA and was adopted as well. 

Quick Stop for Refreshments at Limbers (Hidden Gem!)

Right next to the museum and across the street from the governor’s mansion La Fortaleza, you will find an old “shop” that sells Limber, which is Italian frozen ice for $1. You will see a window with gates and a sign beneath it with the word Limbers on it – walk up to the literal hole in the wall and yell Hola and a nice older couple in their 70s (or their son) will offer you the ice. 

Tip: Get the Tamarind Limber!

Afternoon: Best Tours in Old San Juan

Culinary Food and Walking Tour – combine history with gastronomy in this historic food tour that takes you through Old San Juan’s culinary highlights. Sample local dishes and drinks while learning about the city’s culture – book here!

Alternatively, consider taking a sailing trip around San Juan Bay, where you can enjoy the stunning views of the city and coastline – book here!

In the mood for some art and culture? Then take this tour that focuses on the vibrant art scene and cultural heritage of Old San Juan and visit some of the best galleries in Santurce, street art, and local artisans – book here!

facade of la fortaleza mansion in old san juanStop 7: Explore La Fortaleza (FREE Tour!)

One of the must-visits for Old San Juan and just a short walk away from El Morro Fort, you can find La Fortaleza that’s the current Governor’s house and a former fortress. Further, it’s also the oldest executive mansion in continuous use in the Western Hemisphere, dating back to the 16th century. 

Tip: You can actually tour this place for FREE and run until around 4pm! All you need to do is call +1 787-721-7000 to get a tour. The tours typically last 45-60 minutes and you will hear a lot about the history of the governor’s house as well as Old San Juan. 

History of La Fortaleza

Though it was initially built as a defensive fortification against European invaders, La Fortaleza later evolved into the official residence of the Governor of Puerto Rico. Once you get there, please take a moment and take in its architectural beauty as it blends various styles together, including the Gothic, Renaissance, and Baroque elements, showcasing the island’s rich colonial history – yes, it’s perfect for those insta-shots!

Quick Stop for Ice Cream at Anita Gelato (Not So Hidden Gem – Hidden Gem!)

If you decide to take the tour, you will walk past this gelato place that has absolutely delicious ice cream – like, one of the best I’ve had outside of Italy. The only problem you will face is the wait time that can range from 15 minutes to 2 hours. My recommendation is to go Friday early afternoon when there’s not as many tourists there yet and even there I waited for about 15-20 minutes. During the weekend, you will likely have to go early otherwise you will easily wait 2 hours if not more. Thankfully, there’s at least air conditioning, though. 

Alternative Quick Stop for the Birthplace of Piña Colada (Not so Hidden Gem – Hidden Gem!)woman smiling holding a glass of piña colada and the facade of barrachina bar in old san juan

Before you go anywhere else, take a few steps down the street after your visit at La Fortaleza or Anita Gelato and enjoy an authentic Pina Colada at the bar Barrachina. And let me tell you from personal experience, it’s absolutely delicious and it’s going to be the best one you will have in your life! The wait is totally worth it. If you can, make reservations, if not, ask to take it to go or to sit at the bar. If you have to wait in life, watch the bar seats like a hawk inside and outside as you will get served there much quicker. 

While the price was around $10 (when I went) and the wait time can take up to 30+ minutes, it’s absolutely worth it if you’re a fan of Pina Colada.

If there’s time: Parque de las Palomas

Make a stop at this one-of-a-kind park where you get to feed domesticated pigeons out of your hands – yes, they will literally land on your arms and shoulders and wait patiently (sometimes not so patiently) to be fed. This is such a highlight of Old San Juan that you will never forget. The small kiosk inside sells $2 food bags for the birds, so you can enjoy being a crazy bird person, totally without judgment – and no, they won’t hurt you. They didn’t even poop or scratch us! 

One day in San Juan doesn’t seem to be enough? I feel you! Check out this 3-day itinerary instead.

Don’t miss the beautiful waters! Here are some must-try water activities in Puerto Rico.

Stop 8: Visit San Juan Cathedral

If there’s still time and you can’t get enough, visit San Juan Cathedral, one of the oldest churches in the Americas, and admire the beauty of this church – don’t miss out to look at the stained windows! 

view from the water of castillo san felipe del morro in old san juanHistory of San Juan Cathedral

While it’s known as the San Juan Cathedral, its original name is actually San Juan Bautista, one of the if not the oldest church in the Western Hemisphere, dating back to the early 16th century (wow!). The cathedral was originally built in 1521, making it one of the earliest examples of Spanish colonial architecture in the Americas. 

However, due to frequent attacks by European invaders and hurricanes, the cathedral underwent several reconstructions and renovations over the centuries, resulting in its current Baroque-style appearance. Pay special attention to the striking façade that are characterized by carvings, ornate columns, and a grand entrance adorned with statues of saints.

Stop 9: Visit Castillo San Felipe Del Morro Fort

Only a short walk from the San Juan Gate and the museum, you can explore the El Morro Fort, a 16th-century fortress with stunning views and rich history. On your way there, you may see the famous La Perla, where Despasito was filmed, as well as the famous San Juan cemetery. 

While it’s beautiful to look at from the top, it can be a bit dangerous to go inside La Perla, so I’d not suggest going there by yourself without a tour guide or someone local. However, you can easily visit the cemetery on your own if you have extra time! Alternatively, you can also look at the cemetery from the top overlooking the castillo wall. 

History of El Morro Fort

Castillo San Felipe del Morro, commonly known as El Morro Fort, was constructed by the Spanish starting in 1539, with expansions over the next 400 years. Though its entire purpose has been to defend the San Juan Bay and the city of San Juan from seaborne enemies, such as the English and Dutch who attacked El Morro in the past. Besides protection, El Morro also allowed for controlled access to the bay and the city, which made it a key port in the Spanish Colonial Empire. Today, it’s still a symbol of Puerto Rico’s rich history and the importance in the Caribbean in the past centuries. 

Tip: Stay there for the sunset and enjoy the best sunset views of the island or buy/bring a kite to let it fly through the sunset with other Puerto Ricans.

large land covered in grass with people walking and el morro in the distance contrasting with the sunset

Dinner: Best Restaurants Near El Morro

After visiting the Gate and the Fort you’ve likely already walked for a few hours and walked off the breakfast. These have been my favorite lunch places near the fort:

La Casita Blanca

La Casita Blanca not only specializes in traditional Puerto Rican dishes but the atmosphere is made to be as if you were to visit your Puerto Rican grandmother’s house. All ingredients are locally sourced as the restaurant prides itself in its representation of the islands’ culinary traditions.

Best thing to try at La Casita Blanca:

  • Bacalaitos – Codfish Fritters
  • Mofongo – Mashed plantain with meat or seafood 
  • Arroz con Gandules – Rice with pigeon peas
  • Asopao – Savory Puerto Rican stew with chicken or shrimp
  • Flan de Coco – Coconut Flan

El Jibarito 

Alternatively, you can also go to El Jibarito that’s also a great spot for authentic local cuisine. Located in the heart of Old San Juan, it’s highly regarded for its food, and you can immerse yourself in the island’s culinary heritage. Loved not only by tourists but also by locals (a great indicator of great local food), it gives you everything your heart could desire for lunch.

Best things to try at El Jibarito:

  • Mofongo – mashed plantain with meat
  • Chuletas Can-Can – pork chops
  • Arroz con Pollo – chicken with rice
  • Camarones al Ajillo – garlic shrimp
  • Flan

Evening: Best Tours in Old San Juan

Sunset Walking Tour in Old San Juan – Old San Juan sunset just hits differently among the landmarks, especially as the city’s lights come up in the evening.

Take a sunset walking tour where you can see the city from a different light during the golden hour – book here!

Not really a people person? No worries, I’m not always either! Check this self-guided walking tour that will take you everywhere at your own pace (without the need to interact either) – book here!

Old San Juan Nightlifebuildings and city lights at night in old san juan

I highly suggest checking out some of Puerto Rico’s top nightclubs and pubs if you’re not too exhausted from wandering around and want to get your groove on to some Spanish music!

Though, if you’d rather go on a bar crawl experience, get this one here!

Here are some ideas:

  • La Factoria, which is crowned to be one of the best bars in Old San Juan
  • Club Brava
  • Any of the rooftop bars that you can find on almost every corner of the town

Though, if you get to the Condado area, you will find plenty of bars and clubs to choose from. Many will even have live music and specials on the drinks during happy hour.

Distrito T-Mobile

If you’re down to take Uber to go outside of Old San Juan, you should consider going to DISTRITO T-Mobile that was about a 10-15 minute Uber drive, costing us around $7-8 (this price will depend on the time of the year you’re going and the demand in your area). It’s free to enter the district with a ton of stuff to do and live music.

La Placita

Alternatively, consider also visiting La Placita which is popular for restaurants, bars, and clubs and it’s only a few minutes outside of Old San Juan. It’s popular with the locals and also has a farmers market during the day that’s mostly visited by locals with delicious mangoes and coconut water – so, if you have more time on your hands, definitely pay it a visit!

See my full San Juan nightlife guide here!

Last Thoughts

I hope you enjoyed this 1-day Old San Juan itinerary! If you need ideas for a short day trip and want to see as much as possible in little time, this guide will come in handy. You’ll have the right amount of fun, art, culture, history, and cuisine to keep yourself entertained all day – and you might even decide to stay for longer!



I may collect a small commission from the links on this page if you decide to book a stay, it helps me keep the blog up :) Listed prices are accurate as of the time of publication.

Anna is a traveler, blogger, and entrepreneur who can’t keep herself still. She’s always on the move, whether working hard on a new passion project or exploring a new city as a part-time digital nomad. Dare to keep up? Check out The Tatted Nomad for everything digital nomad, social media marketing, mental health, and travel (and to see her latest addition, Novah, her service dog and travel companion). As a psychotherapist (to be) she also offers insights about your mental health related questions – anything you see that isn’t covered but you have questions about? Let her know!

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