Best Things to do in Old San Juan, Puerto Rico: How to Go on a Self Guided Walking Tour

Home » Best Things to do in Old San Juan, Puerto Rico: How to Go on a Self Guided Walking Tour

Last Updated on April 7, 2020 by Paroma

Puerto Rico, formerly a Spanish armed force and naval base, is an U.S. territory and a small island in the Atlantic Ocean, with tropical climate and beautiful, sun kissed beaches. Most people flock to this island to enjoy their time on the beach resorts in the newer Condado part of San Juan. However for lovers of some old world charm will find solace in the beauty and vivacity of old town Puerto Rico which is a bridge and 10 min drive from the Condado/airport area. There are plenty of things to do in old San Juan during your Puerto Rico itinerary, which will mesmerize you with its beauty, colonial architecture, colorful houses and of course, a lot of history hanging on to its air like a musty cobweb. 

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I have visited this city twice and have explored the old San Juan attractions simply by walking everywhere on its cobbled streets. So here is an account of my self-guided tour of old San Juan, which covers most of the sightseeing in old town if you have three days in hand. So here my take on this part of the capital city, with tips on where to stay in San Juan, Puerto Rico, things to see in old San Juan, places to do some old San Juan shopping, and of course, tips on where to find some of the best restaurants in old San Juan.  

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Best things to do in old San Juan

There are so many things to do in Old San Juan and the best way to explore them is by foot since the city is spread out like a grid and is thus very walkable. If you have semi-winged appendages, i.e. overly eager feet and are a  champion walker, you can explore the entire old town in two days. If walking is really not your scene, take the free green trolley to the major attractions of old San Juan that have several stops all over town and the stops are clearly demarcated. Here are some of the top things to do when you are exploring old San Juan:

 

1) Admiring the colonial architecture

Old San Juan is indeed a beauty with her wares on full display, seeped in history starting from when Christopher Columbus first landed foot in 1492 to the modernities of today’s age reflected in the cafes, occasional fast food chains and other amenities jostling for space with the historic buildings. The houses hark back to the Old Spanish colonial style, with dark wooden doors and windows that are slatted, beautiful pastel, neon and all other shades of colored walls and inner courtyards, very much in the Andalusian style. This website has a brief history of the Old San Juan architecture and its primary attractions and is a fun read for history aficionados.

This is a guide to the best things to do in old San Juan and features the top Sn Juan attractions

Some of the best places to view colonial architecture in old San Juan are the following:

a) Calle de La Fortaleza: This is the artery of old San Juan and is flanked by beautiful, colorful homes on either side

b) The Casa Blanca (White house): this National Historic monument, built in  the 1520s for the Ponce de León, stands pristine on Calle San Sebastian and is home to a museum.

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c) San Jose Church: An excellent example of Spanish Gothic architecture, this beautiful church is located on Plaza de San Jose.

d) Palacio Rojo: This Baroque style building is on one end of Calle La Fortaleza and houses administrative offices

e) Palacio Episcopal: This continues to serve as the private residence of the Bishop of San Juan and is located on the Avenida de la Constitución.

One of the best things to do in old San Juan is explore Calle Fortaleza
Calle fortaleza in old San Juan

 

 

2) Visiting the Spanish Forts

Old town boasts of the two Spanish fortresses Castillo Morro and Castillo Cristobal, two must visit World Heritage sites in San Juan that were built by the Spanish to protect this good port (i.e. Puerto Rico) from being invaded by other European forces (Dutch/French). These fortresses stand tall and proud on the north and east ends of the city and are must visits.

Castillo Cristobal was built in 1634 and was once considered the Gibraltar of the West Indies. This fort is one of the largest defenses ever built in the Americas and is currently a World Heritage and National Historic Site managed by the U.S. National Park Service.

Castillo Morro overlooks the San Juan Bay and is the labor of love of Spanish engineers over a period of 250 years (1539-1787). This was considered to be the grandest fortification built by the Spanish in the Caribbean. Once atop the fort, you will get one of the best views in Puerto Rico of the old town shoreline along with a peek at the dotted white tombstones of the cemetery below. You can either walk along the guarded wall or adjacent paved way from one fort to the other or simply take the trolley.

Castillo Cristobal and Castillo Morro are two must visit sites on your old San Juan self guided walking tour
Castillo Cristobal and Castillo Morro are two must visit sites on your old San Juan self guided walking tour
 cemetery at the foot of Castillo Morro , Old San Juan

 

3) Exploring museums

i) Museo de Americas

San Juan is home to a few small, yet lovely museums hosting exhibits that you will not find elsewhere in USA, thanks to it being a territory and not a state. If you are a history buff, I strongly suggest visiting the Museo de Americas during your old San Juan walking tour which is one of the most beautifully curated museums that I have ever visited and one of the hidden gems of Old San Juan.

Museo de Americas is a must visit if you are an art and history buff

At a ridiculous entry free of $6, you get to see painstakingly detailed exhibits spanning the history, origins and anthropology of Puerto Rico, the folk art of the island, the information on the original Taino people who inhabited the island, the  arrival of the Europeans and finally the advent of the African slaves. All three races have influenced the island’s checkered and often turbulent history and left their mark on its cuisine, culture and music.

Museo de Americas, Old San Juan, Puerto Rico

There is an entire section of this old San Juan attraction devoted to the horrors of slavery as a part of Puerto Ricans to understand their African heritage, and this is something you will not see anywhere in mainland USA. So prepare yourself to encounter a very vivid narrative of a very dark past of the Americans, that includes a display of the torture devices to punish the runaway slaves. Although I pride myself on having an iron stomach for most atrocities in man’s history, this was something very difficult to accept visually. Some of the exhibits on the lighter side were paintings on modern day symbolism and holograms of famous personalities, showing two sides of a coin.

Museo de Americas is one of the many old san juan attractions
Museums of old San Juan
Slavery exhibit in Museo de Americas in old San Juan

 

 

ii) Museo de San Juan

I also peeked into the Museo de San Juan, another one of the many things to do in old San Juan, which is a free one and had only two galleries, one of which was devoted to the different translations of Don Quixote, the famous book written by the Castilian author Miguel De Cervantes and is the most translated book in the world after the Holy Bible. I managed to take photos of the books translated in Indian languages such as Hindi and Bengali, but apart from that the exhibit had nothing much to offer unless you are a true blue linguist.

Museo de San Juan, another one of the many things to do in old San Juan, which is a free one and had only two galleries, one of which was devoted to the different translations of Don Quixote
Self guided walking tour of old San Juan

 

4) Walking down Paseo de la Princesa

Paseo de la Princesa should definitely be on your self guided tour of old San Juan. This is a beautiful promenade towards the harborside where you can go on a tranquil evening walk to catch the last rays of the sun glistening on the waters of the Atlantic. You will see the Governor’s palace, a beautiful garden with a small fountain (called fountain of youth), ships passing by and a trail that leads to the Castillo Morro. The red San Justo gate stands tall and proud at the point where the trail starts and it is considered to be the entry way for Spanish Officials into the island starting from the 1500s.

Paseo de la Princesa should be on your Puerto Rico itinerary

At the center of this old San Juan point of interest stands a statue made of several figurines that depict the spirit of Puerto Rico, its people, its origins and its hopes and aspirations. A fountain caresses this statue which was unveiled to coincide with 500 years of Columbus’s arrival on this island. There are several other statues found in the plaza (called Plaza of the Heritage of the Americas) nearby which were sculpted by Jose Buscaglia which represent the various sources of the heritage the Americas (Fuente de la Herencia de las Américas)-that of faith, blood, Hispanic heritage and Intellectual heritage. There is also a small garden with the statue of Elisa Rincón de Gautier where you can sit and relax.

Paseo de la Princesa is a top attraction in old San Juan
things to do in old san juan puerto rico, Paseo de la Princesa
Paseo de la Princesa
Paseo de la Princesa sculptures

 

 

5) Checking out Avenida de Constitución

Of all the things to do in Old San Juan, I really enjoyed my walk along the Avenida de Constitución that skirts along the Castillo Cristobal, where  the Capitol is located along with other administrative buildings. These were are anything but the staid, plain government buildings that we see elsewhere in USA. Brightly colored with ornate architecture, they too are very picturesque.

Check out Avenida de Constitución during your 3 day visit to old San Juan

Avenida de Constitución is one of the many old san juan attractions

As you walk down this one way street, you will see 8 bronze statues of American President (including President Obama) on the pavement called Presidential walk. These are of the sitting presidents who have visited Puerto Rico while they held office.

Puerto Rico capitol building on Avenida de Constitución

The capitol is also open to visitors, but I was running low on time during my Puerto Rico itinerary and thus had to be content by clicking photos from the outside. In addition, there is the Puerto Rico police memorial as well as the holocaust memorial for the Jewish population inhabiting the island.

What to see in old San Juan-Avenida de Constitución
Avenida de Constitución
President Obama on Avenida de Constitución

 

6) Souvenir shopping in old San Juan

Shopping in Old San Juan can be somewhat of a disappointment for those looking for local artisans and boutiques. Most of the old San Juan shops sell cheap souvenirs and trinkets, catering to the tourists and the remaining are the impersonal chains such as a Coach factory or Tommy Bahamas.

things to do in old san juan puerto rico, street art of San Juan

I still managed to find two amazing old San Juan stores in this sea of commercialization, who represented a slice of this town in their works and recommend them as places to shop in old San Juan. My favorite was Mi PeQueno San Juan (152 Calle Fortaleza) which is an artists shop selling replicas of real Old town doors, handmade from scratch. These were mini versions of the beautiful andalusian architecture that you will find yourself surrounded by, during your old San Juan walking tour, and can be customized with your name. They were so beautiful that I simply had to buy one (see photo below).

shopping in old San Juan on Calle Fortaleza

The other store is called “Sea Foam Rare and Authentic” (101 Calle Fortaleza) and here I found the prettiest, nickel free copper earring etched with delicate patterns (see photo below).

What to do in old San Juan, self guided walking tour
Colonial architecture of San Juan

 

 

7) Eating out in old San Juan

San Juan is having its moment of glory in the American Culinary scene and Old San Juan’s restaurants are a testimony to the creativity that is overtaking the island food. So if you are wondering where to eat in Old San Juan, you will be spoiled for options. Please stay away from all the tourist traps selling garbage and follow this foodie’s, aka my, trail for lip smacking food that fits all budgets. Here are some of my suggestions on where to eat in old San Juan:

Best places to eat in old San Juan, San Juan street food, Piragua

i) Old San Juan street food: Start off with some fresh coconut water (straight out of a coconut) or Piragua (Puerto rican crushed ice with syrup) at one of the vendor stalls in the city squares

ii) Old San Juan restaurants: Have a quiet breakfast in the serenity of Patio del Nispero in Hotel El Convento, get hold of some amazing Latin-Asian fusion food at DragonFly, try some sumptuous mofongo (Puerto Rican mashed plantains stuffed with fillings, a food of African origin) at its sister establishment Aguaviva (right next door) or the amazing four/five or six course menu at Marmalade (Best restaurant in San Juan, hands down and right across from my hotel and has a whole vegetarian section).

street food in old San Juan

iii) Old San Juan Cafes: Don’t forget to get breakfast La Parisian style at Cafe Berlin (lots of vegan/vegetarian choices available including vegan mofongo), cold drinking chocolate and chocolate-hazelnut paste filled croissant at Chocobar Cortes chocolate bar and finally some Mallorca (sweet bread with powdered sugar) at one of the best places to eat in old San Juan, i.e. the famous La Bombonera cafe. 

San Juan buildings

 

Where to stay in Old San Juan, Puerto Rico?

I strongly recommend Hotel Casablanca, a Moroccan themed hotel on Calle Fortaleza, in the heart of the city where I stayed during my second visit and loved the convenience and service! Seriously, If you are looking for a budget boutique hotel in the heart of old town, Casablanca is possibly one of the best hotels in San Juan. Unlike what it says on the website, the hotel now has a functioning elevator so you don’t have to huff and puff up the stairs with your luggage in tow.

Hotels in old San Juan-Hotel Casablanca

The hotel is very vintage, very quirky in its choice of wall paintings (eclectic, pop-art kind of) and has delicate Moroccan touches such as lamps and chandeliers. The rooms are very modest with a bed, two side tables and separate washrooms for bathing and doing your business. There is also a flowing mosquito net that hangs from the top and  lends a touch of bygone-era class to the otherwise spartan decor. The funniest thing that caught my eye at that time was the continuous playing of the famous movie “Casablanca” on loop on the hotel lobby monitors.

View from the rooftop of Hotel Casablanca, one of the best budget hotels in old San Juan

The rooftop offers a good view of the city and is free to all guests. The room rates are surprisingly on the cheaper side (less than $130/night) for the location and popularity of the hotel. The front desk is active 24/7 and you can request them for any reasonable amenities. Finally, there is free WIFI which you cannot beat! Again, I HIGHLY RECOMMEND this charming, quaint hotel in the heart of Old Town in lieu of the monstrosity of the resorts in the Condado area that you’ll encounter during your San Juan, Puerto Rico vacation. It’s centralized location is a big plus for your self guided tour of old San Juan.

 

This in a nutshell, was my take on things to do in old San Juan, a city I revisited this year and the one I love coming back to. I hope you get to visit it someday too in your travels and enjoy its offerings and beauty as much as I have. Do share your travel experiences with me and let me know if you found my tips helpful. As promised, click below to download your free PDF itinerary of old San Juan.

DOWNLOAD THIS FREE OLD SAN JUAN ITINERARY NOW!

 
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Old San Juan self guided tourThis is a complete self guided walking tour of old town San Juan, the best part of Puerto Rico, USA. This post is a must read for discovering the best things to do in San Juan's old town and includes a budget boutique hotel, plus a walking tour of the city's vibrant art, architecture and museums. Pin this to your USA or Caribbean travels board now! #USA #Caribbean #PuertoRico #SanJuan

 

This is a complete self guided walking tour of old town San Juan, the best part of Puerto Rico, USA. This post is a must read for discovering the best things to do in San Juan's old town and includes a budget boutique hotel, plus a walking tour of the city's vibrant art, architecture and museums. Pin this to your USA or Caribbean travels board now! #USA #Caribbean #PuertoRico #SanJuan

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10 thoughts on “Best Things to do in Old San Juan, Puerto Rico: How to Go on a Self Guided Walking Tour”

  1. I’ve been to Puerto Rico several times, but have not made it to Old San Juan yet! I just love historic cities like this! We have been to Rincon several times…..you have to visit if you ever get a chance!

    Reply
  2. Great list! I’ve twice had all-day layovers in San Juan (en route to St Croix) and have wandered around Old Town both times – I love how colorful the buildings are!

    Reply
  3. Absolutely love this post as it reminded me of my time in San Juan. I love your photos and this is very detailed information.

    And like you, definitely not one to stay in the beach throughout my holiday. I’ll get bored out of my mind and my adventurous side will be screaming for an escape. I do love some time by the beach towards the end of my trip though. Just so I can end it on a relaxing note.

    Great post, thanks for sharing.

    Reply
  4. Very informative post on Puerto Rico. I plan on going there soon. I’ll be saving your post. BTW is that rooster real?

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  5. I was in San Juan about a year ago, and you have perfectly captured the city! I’d love to get back. It’s safe, friendly, and historic. Great job!

    Reply
  6. These photos are so stunning! I’ve never been to San Juan, but I would absolutely love to go! Will definitely keep your recommendations in mind if I ever make it over there!

    Reply
  7. More than anything else, your vivid description and stunning photos makes me want to jump from where I am right into the photos! Very nice captures! Keep up.

    Reply

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