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One Day in Old San Juan, Puerto Rico - Calculated Traveller

A Walking Tour Itinerary for One Day in San Juan Puerto Rico

Author Mary Chong
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San Juan, Puerto Rico, is such a great port stop – you are right in the middle of Old San Juan, and it’s a very accessible access point for sightseeing, shopping, good eats and, of course, exploring the culture – all within walking distance.

This one-day itinerary is focused on someone travelling by cruise ship because that’s how we usually visit San Juan. But, this tour is adaptable to anyone who is in a time crunch and only has one single day to explore this historic city.

A Walking Tour Itinerary for One Day in San Juan, Puerto Rico

One Day Tour Itinerary for Old San Juan Puerto Rico by Calculated Traveller

1. History of San Juan Puerto Rico

The capital of Puerto Rico, San Juan, is filled with history and is becoming one of the most popular Caribbean tourist spots. From pirate attacks to naval battles, the rich history of San Juan is evident as you walk through the centuries-old blue cobblestone streets (The cobblestones are made from the broken pottery from the ships that were originally used as ballast). Originally founded by Ponce de Leon.

Today visitors flock to San Juan for the arts, culture and vibrant nightlife. The old city is filled with carefully reconstructed buildings from the 1800s, like churches, museums and homes. With a wide variety of landscapes within a radius of the city, you can be in a tropical rainforest or lounging on the beach in no time. For Americans, another draw is you don’t need a passport as you are on American soil.

San Juan is also one of the most important ports in the Caribbean to deliver not only tourists but there are also refineries producing sugar, pharmaceuticals, oil and more. It’s easy to see why San Juan has become a popular destination, especially for cruise ships! Although ideally, you could spend a week here or longer, many times when you are visiting on a cruise ship, you may only have a day to see everything this old city has to offer.

2. Start at the Port Terminal Calle Marina

One Day in Old San Juan Puerto Rico

Grab a big breakfast this morning and a comfortable pair of shoes as we start this adventure! Your cruise ship will likely be docked at the Port Terminal Calle Marina. Once you leave the ship to spend some time on the water’s edge, there are shaded benches along the way as well as a nice breeze. Continue over the bridge to the park.

One Day in Old San Juan Puerto Rico - Bahia Urbana San Juan

3. Bahía Urbana Waterfront Complex

Bahia Urbana One Day in San Juan Puerto Rico

This is an entirely new waterfront park that opened in 2013. It is still being developed and things are constantly changing. There are some lovely sculptures and fountains, a café and open-air concert area, so take a brief stroll through and take it all in.

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4. El Capitolo de San Juan

El Capitolo One Day in San Juan Puerto Rico

The Capital of San Juan, built in the 1920s is home to the House of Representatives and Senate. You are free to enter the building, and you really should take the time to visit there. There is a beautiful mosaic ceiling in the central hall. Make sure you continue through the building and out the back entrance.

The capital is open Monday to Friday, 8:30 am to 5:00 pm.

One Day Tour Itinerary for Old San Juan Puerto Rico by Calculated Traveller. Photo of the ceiling of the Capital Building. #SanJuan #PuertoRico #travel #Caribbean

There is a lovely view of the ocean from the street as you continue your journey toward your next stop, but if you take the stairs down, you’ll come to Playa Pena – the only beach in Old San Juan. There you can relax for a moment in the sand or dip your toes in the crystal-clear water.


One Day in San Juan Puerto Rico - Playa Pena.

5. Castillo San Cristóbal / Fort San Cristóbal

One Day in San Juan Puerto Rico - Castillo San Cristobal

The fort was built between 1634 and 1790, and is part of the National Park Service, and Ranger-led tours are available, or you can explore on your own. If you go to the top south wall of the upper level, there is a doorway that provides great views of the cruise ships down below, and it makes a great photo spot!

Open daily from 9:00 am to 6:00 pm – except on Easter, Thanksgiving and Christmas (age 16+).

Read more in the article Fort Castillo San Cristobal in Old San Juan, Puerto Rico

6. Plaza de Colon

Plaza de Colon One Day in San Juan Puerto Rico

Named for the explorer Christopher Columbus, this plaza and statue were built to commemorate the 400th anniversary of the discovery of the island. This plaza is a favourite spot of ours. We like to have a rest in the square, people watch, and always visit the local food court on the north side of the plaza (free restroom inside) to taste the roasted pork and empanadas. Continue along Calle San Francisco and check out the shops as you make your way to our next stop.

Check out this article to read more about my favourite empanadas in Old San Juan.

7. Cathedral of San Juan Bautista

Cathedral of San Juan Bautista One Day in Old San Juan Puerto Rico Calculated Traveller

The Cathedral is open daily and is free to enter and tour. Be aware that regular church services occur daily, so you will need to be mindful and respectful of worshipers. Built in 1540, this is the oldest cathedral in the US and territories and also is where the body of Ponce de Leon is entombed.

8. La Rogativa

La Rogativa One Day in Old San Juan Puerto Rico

Standing twelve feet high, this statue commemorates San Juan’s 450th anniversary and also offers some amazing ocean views. Completed in 1971 by Lindsay Daen, this bronze statue is a must-visit. After your visit, head back down the street to the red-walled entrance to the lower wall.

9. Old San Juan Wall

One Day in San Juan Puerto Rico

Walk along the water’s edge, where you can see how well-fortified the Old City of San Juan truly was. Watch out for the feral cats that seem to be everywhere along the path – they are harmless but plentiful. There is also a massive banyan tree just through the gate, which provides a nice cool shade to go with the cool breeze of the ocean. If you aren’t interested in shopping (see B and C below), walk along the wall and the tree-lined Paseo de la Princesa so you can see the most beautiful of water fountains Raices Fountain.

Raices Fountain One Day in Old San Juan Puerto Rico Calculated Traveller

10. The end of our tour

By now you’ve followed along the many cobblestone streets and window-shopped the many liquors, silver jewellery and artisan wares. The cobblestones are a distinct blue and are made from the broken pottery from the ships that were originally used as ballast. At this point in this little tour, you are back on the waterfront, where you can perhaps hire a horse and buggy, visit more vendors or walk back to the ship.

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Optional Stop A. Castillo San Felipe del Morro / El Morro

El Morro One Day in San Juan Puerto Rico

This 16th Century fort is what you likely saw as the ship sailed into port. It’s a huge fortress with six levels of fortification and something that everyone should tour at least once in their life. The only downside is that it’s a bit of a trek out and will likely take time away from other sites in Old San Juan.

Open daily, 9:00 am to 6:00 pm. $5 (age 16+)

Nearby El Morro, you’ll find Santa Maria Magdalena de Pazzis Cemetery. Dating back to 1863, this cemetery houses some of the most powerful and famous people in Puerto Rico. Not only do you visit for the history, but it also has breathtaking views.

A Guide to San Juan by Calculated Traveller. Santa Maria Magdalena de Pazzis Cemetery | #SanJuan #PuertoRico #guide #tour #travel

Optional Stop B. Shopping Old San Juan

Yes, of course, there are regular tourist shops for handicrafts, t-shirts and jewellery, but in the area of Calle del Cristo and Calle Fortaleza, you will find a few designer outlets such as Coach, Ralph Lauren and Dooney and Burke.

One unique shop is the Butterfly People Art Gallery, 257 Calle Cruz, just north of Calle Tetuan. They have the most amazing works of art entirely made from butterflies.

Looking for a Panama hat? Visit world-renowned Olé Curiosidades at 105 Calle Fortaleza (between Calle del Cristo and San José). Owner Gustavo Lerner has made hats for some very famous people, and you could just be one of them. Each piece is measured and customized for you.

Optional Stop C. Barrachina Restaurant

Barrachina Restaurant is said to be the place where the pina colada was first made in 1963. I don’t know about that being true, but the décor is nice, you can taste some Puerto Rican cuisine, and Friday and Saturday evenings include entertainment and dancing. Also to note is that they also offer a free luggage storage area for customers (9 am to 5 pm) if this is your last day in town. We’ve used this service before and had no issues at all. We spent the day touring and then returned to our luggage and had dinner before our flight home.

One Day Tour Itinerary for Old San Juan Puerto Rico by Calculated Traveller | #SanJuan #PuertoRico #tour #travel #walk

Please check out our Caribbean archives for more itinerary suggestions for other ports on your cruise holiday.

Exploring further? Read our travel guide 10 Absolute Best Things To Do In Puerto Rico


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