Home Americas How To Go On A Self guided Tour of Old San Juan

How To Go On A Self guided Tour of Old San Juan

written by ParoChak May 29, 2016
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

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 (85F throughout the year) and beautiful, sun kissed beaches. Although most people flock to this island to enjoy their time on the sand and under the sun, stay in the resorts and hotels that have mushroomed in the Condado part of San Juan, the capital, and generally get smashed at the numerous surrounding bars, my idea of holidaying does not include any of these. I am not a beach person, I generally abhor water, I do not like lying down and doing nothing  (that too under the blazing sun) and I clearly do not like the idea of a vacation with alcohol racing through my veins. So no Condado for me por favor, it has to be the old world colonial charm of Old San Juan, a bridge and 10 min drive from the Condado/airport area, which is full of beauty, amazing architecture, houses painted in myriad colors and of course, a lot of history hanging on to its air like a musty cobweb. Old San Juan, with its painted homes and cobbled streets is one of my favorite cities to visit and revisit and this time, I explored it quite a bit via my self guided tour of Old San Juan. So here my take on this part of the capital city, with tips on where to stay, major attractions, places to shop and of course, lip smacking restaurants.  For more ideas on Puerto Rico, read my other blog post on traveling solo here.

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

Old San Juan: STAY

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

Old San Juan has a good mix of stereotypical touristy hotels (new establishments), apartments/houses with Airbnb and historic establishments such as the El Convento hotel (a 17th century convent now converted to a luxe hotel with a beautiful dining courtyard) or Hotel Casablanca, a Moroccan themed hotel on Calle Fortaleza, in the heart of the city. 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. 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 wash rooms 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. 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! 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. It’s centralized location is a big plus for your self guided tour of old San Juan.

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

Old San Juan: EXPLORE

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

Old San Juan:HOMES

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

Old San Juan is a series of cobbles streets criss-crossing each other in a grid and is thus very walkable. If you have semi-winged appendages, i.e. overtly 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 that have several stops all over town and the stops are clearly demarcated. But honestly, just get out of your hotel and start walking around and I guarantee that you will have to stop every few steps to take in the breathtaking view of the surrounding riot of colors, the beautiful colonial architecture of the homes, the fiery reds and pinks of the tropical flowers such as the Delonex regia (“Krishnachura” in Hindi/Bengali) and Bougainvilleas and the intercepting greenery of the almond trees and other tropical plants that you will be hard pressed to find in the upper 48 states. 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.

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

Old San Juan: ATTRACTIONS

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

All attractions of Old San Juan are majorly navigable on your self guided tour of old San Juan, thanks to the pint-sized city and its walkability, and is a nod to its past history. Old town boasts of the two Spanish fortresses Castillo Morro and Castillo Cristobal, which were built by the Spanish to protect this good port (i.e. Puerto Rico) from being invaded by other European forces (Dutch/French) and are declared as World Heritage sites. These fortresses stand tall and proud on the north and east ends of the city and are must visits. Once atop the Castillo Morro, you will get a breathtaking view 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.

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico

If you are into museums, I strongly suggest the Museo de Americas in old San Juan, which is one of the most beautifully curated museums that I have ever visited. 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. There is an entire section 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.

Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
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Old San Juan Travel Puerto Rico
Old San Juan Travel Puerto Rico
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Old San Juan Travel Puerto Rico

My favorite exhibit though was the first gallery which focused on the 20 indigenous native tribes living in USA, mesoamerica and the Amazon valley, that have somehow survived the hundreds of years of European conquest and the death and destruction brought in its wake. These tribes range in number from a few hundred to several thousands and their way of life is rapidly being washed away by modern man’s greed, yet they somehow hold onto what is sacred to them. The most moving part were the twenty cast iron statues of real tribe members that were made by an European guy who had flown into these remote areas to meet the tribes, choose his model, get their plastered moulds and make the statues. There is a very nice video that showed footage from the artists quest of making these sculptures, as a means to respect these tribes and make amends for the cruelty inflicted on them by people invading their way of life and taking away their land. As another brown person who has been influenced by the vestiges of western colonialism, I could not help but empathize with the brutality that native tribes have endured all over the world as they watched their way of living being snatched away from them. Very poignant and a beautiful reminder of vanishing cultures and the price one pays for human greed and disrespect. I highly recommend this museum for fellow history and culture lovers.

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I also peeked into the Museo de 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.

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Old San Juan Travel Puerto Rico
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Old San Juan Travel Puerto Rico

Finally, there is a beautiful promenade towards the harbor side called the Paseo de la Princesa, that you must take a stroll along in the evening 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. At the center of this promenade 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 Americas)-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.

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Old San Juan Travel Puerto Rico
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Cut to modern day politics and that is exactly what you will find along the Avenida de Constitucion that skirts along the Castillo Cristobal, where  the Captiol is located as well as other administrative buildings are, which again are anything but the staid, plain government buildings that we see elsewhere in USA. Brightly colored with ornate architecture, they too are very picturesque. 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. The capitol is also open to visitors, but I was running low on time 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.

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Old San Juan Travel Puerto Rico Barrack Obama US President 44
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Old San Juan: SHOP

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Shopping in Old Town can be somewhat of a disappointment for those looking for local artisans and boutiques. Most stores sell cheap souvenirs and trinkets, catering to the tourists and the remaining are the impersonal chains such as a Coach factory or Tommy Bahamas. I still managed to find two pretty gems in this sea of commercialization, who represented a slice of this town in their works. 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 in the city and can be customized with your name. They were so beautiful that I simply had to buy one (see photo below). 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).

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Old San Juan: EAT

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San Juan is having its moment of glory in the American Culinary scene and Old town’s restaurants are a testimony to the creativity that is overtaking the island food. So pretty please stay away from all the tourist traps selling garbage and follow the monkey’s trail for lip smacking food that fits all budgets. 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, 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 Dragon Fly, 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) and 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 Casa Cortez chocolate bar and finally some Mallorca (sweet bread with powdered sugar) at the famous La Bombonera cafe. Puerto Rican food comprises mainly of meat and fish (I had my fill of the latter) but sides such as rice, beans, plantains (island staples) can help tide the vegetarian folks. Read my detailed blog post on food here.

This in a nutshell, was my take on 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. Thanks so much for stopping by!

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Old San Juan self guided tour

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10 comments

April Rodrigues August 30, 2017 at 5:18 pm

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!

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Leigh August 31, 2017 at 3:52 am

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!

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Ufuoma August 31, 2017 at 10:55 am

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.

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Kareemah Ashiru August 31, 2017 at 11:29 am

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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ELT August 31, 2017 at 11:30 am

Stunning pictures and seems you have got yourself throughly acquainted with this “pint-sized” city 😉

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Suzanne Ball August 31, 2017 at 11:38 am

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!

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Jess // writinginredlipstick August 31, 2017 at 3:02 pm

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!

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BONNITA ALUOCH August 31, 2017 at 6:34 pm

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.

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Jen Horsfall September 1, 2017 at 7:34 am

Wow your photos are stunning, such a detailed post too. Puerto Rico is on my bucket list for sure.

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Julia September 1, 2017 at 1:58 pm

Literally a rainbow on earth Old San Juan! I just love how authentic the street art looks too!

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