Ever wondered what it’s spend a few hours under the Caribbean sun in the one of the oldest cities in the Americas- getting lost in the cobbled stoned streets, striking up conversations with locals (who all seem to oblige your requests to take a photo of you with a smile, so if you are a solo wanderer like me, don’t fret), to be carried away by the sounds, colours and excitement that you won’t even second guess why you’re not lazing around on a white sand beach?

You are after all, on holiday in the Caribbean.  If you have, keep reading and perhaps at the end, you’ll find yourself getting a ticket to San Juan, PR so you can journey through the “calles” of Old San Juan. 

If you aren’t staying in Old San Juan, you’re probably staying in Condado (where I stayed on this recent trip), Miramar, Isla Grande or one of the other neighbourhoods in San Juan. I recommend staying in Condado as it has a few beaches of its own, good restaurants and decent nightlife. An evening stroll along the main road, Avenida Ashford, which runs through the nieghbourhood, is reminiscent of Miami Beach due its Art Deco buildings, coupled with modern upscale condos and hotels. Condado is a brisk 30-40 minute walk to Old San Juan, or an 8-10 minute drive, traffic depending.

I tried to wrangle a couple of my friends that I was on the trip with, but it was their birthday trip and their main agenda was to get some R&R. Plus, they had arrived two days before me and had taken an evening stroll through the old city; and even though I knew there was more to see, I relented, hopped in the car and within 10 minutes found myself parked on Calle del Sol, in Old San Juan. 

I couldn’t help but to let out a chuckle after parking because the street I ended up parked on, Calle del Sol, translates to, “street of the sun” and as someone that is an avid lover of the sun- it’s warmth and light, I found it rather serendipitous that I would begin my journey through old San Juan on this street. Now, this wasn’t my first time in the old city, as I had visited PR in September 2015, so I knew a bit of what to expect, but I was still excited about exploring new corners, stumbling on new murals, chatting it up with shop owners and enjoying the rich vibrant textures of the buildings.  My first encounter was with a familiar sight, a cat- one of many you’ll see around the old city, mostly taking refuge from the glaring hot sun and occasionally getting up to stretch.

As I continued up the street, I asked a local to direct me to a mural I had visited before, a rather popular one in Old San Juan that I intended to use as point of reference in my city strolling.

 While walking towards the mural, I spotted a picture perfect home, painted in a mix of turquoise and cyan blue, with a large potted plant in front, as well the Puerto Rican flag waving above. I did what you are bound to do countless times whilst exploring the old city, which was to pull out my phone and start snapping some images. I felt like the scene was too perfect not to insert myself, so I scanned the street to see who could take my photo. I saw someone who not only had an iPhone in hand, but also a camera backpack, with a tripod on the side. Perfect! I was confident that he would be able to capture the image I had in mind, which as a traveller who largely relies on strangers to take my photos is a blessing. I handed him my phone, stood in the middle of the street and he began snapping. Since the house was at the corner of an intersection, a few cars kept passing by, but not one of them honked their horn for me to get out of the way, and some even waited until he finished taking the images before driving by.

I also took a few images of him on his phone and asked for his Instagram, so I could credit him when posting the image.  Turns out, he  is a bit of a traveller himself, as well as a photographer and was visiting by way of New York City as well. Do check out his page when you have a moment.

Soon after, I turned on Calle San Jose, where the mural I was in search of is located. It’s called “La Puerta de la Bandera” and a local artist, Rosenda Alvarez, first painted it about seven years ago. It’s now somewhat symbolic to the identity of the island, which is why in 2016 she repainted the red, white, and blue bandera in a more somber black-and-white reimagining. It was meant to highlight the newly imposed fiscal oversight board on the island which I can only guess was not met with welcomed approval from most locals and it still remains black to raise awareness to the devastation caused by Hurricane Maria in 2017. I’ve been fortunate enough to see it in both renditions and I can attest that regardless of its colours, it is worth pausing at and admiring.

Aside from revisiting “La Puerta de la Bandera”, I had nothing else planned, which is how I think you should go about exploring Old San Juan, little to no guidebooks or maps (unless there’s a particular shop or street you want to find), but rather following your senses; let your eyes guide you through  vibrant pastel coloured buildings,

speak with locals and get their suggestions of their favourite places for lunch,

let the faint ocean breeze pull you from the cobble stoned corridors to Castillo San Felipe del Morro, a 16th- century citadel on the banks of the San Juan Bay, that is also a UNESCO World Heritage Site where you can rest your legs on the lawn and fly kites.

Let your ears take you to Plaza de San Jose, popular for its bars and lively music, find shade under the recent umbrella art installation on Fortaleza Street while sipping on a pina colada from one of the nearby restaurants

and if you’re feeling slightly adventurous, head to Parque de las Palomas. It’s a small outdoor park that not only boasts some pretty gorgeous city and ocean views, but also is home to dozens of pigeons that will without hesitation climb on your arms, shoulders and other body parts if you are offering them food. I see more than enough pigeons in New York, so I wasn’t as inclined to feed, let alone have them climb on me, but you know it’s one of those things you can say you’ve done. 

 So, what are you waiting for? Go get lost in Viejo San Juan and find your own journey!