At first glance, flying in on a tiny, rickety prop plane from St Thomas, I wasn’t overly impressed with San Juan, Puerto Rico. From the air, it just seemed like a huge, sprawling city, and from the ground, it seemed like a foreign and chaotic maze of multi-laned highways and questionable driving tactics that had me seriously doubting my decision to rent a car. But after a solid night’s sleep, I was ready to give it a chance to dazzle… And dazzle it did. Puerto Rico-21

As soon as the AC in my hostel dorm switched off at 7am, I braved the streets for the second time, feeling much better about the whole driving situation in the light of a new day. Parking on the edge of Old San Juan, I grabbed my camera and peanut butter sandwich and set out to Explore.

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As I walked down the bright cobblestone streets of Old San Juan, I felt as if I were somehow magically transported to Europe. Colorful homes lined the narrow, winding streets, their balconies overflowing with potted gardens and cats. Lights were strung up back and forth across the streets, and music and laughter spilled out of the corner cafes (along with smells that made my peanut butter sandwich seem a tad less desirable than normal.)

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Nestled in the shadow of the towering wall that has stood guard over Old San Juan for centuries, the quaint, charming, sun-sparkled city takes you back in history and makes you never want to leave.
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I started the morning by walking the Paseo del Morro, a 1.5 mile path at the outside of the wall that winds along the coastline with beautiful views of the El Morro Fort (Castillo de San Felipe del Morro,) San Juan Bay, and Fort San Juan de la Cruz on the other side of the bay. The wall is staggering, and I took entirely too many photos of it but it was impossible to stop. Coupled with the deep blue of the bay opposite it, it was an idyllic setting that made the artist in me do a little happy dance.

Puerto Rico-29Puerto Rico-8Puerto Rico-26Since I was there early, I was the only person on the Paseo… except for the cats. After spending just a few hours in Old San Juan, I began to think that the cats roaming the streets were as plentiful as the cobblestones under their paws. They kept me company on the walk—all colors, shapes, and sizes of them, some rather ferocious, and others supremely cuddly. There are signs posted around the city warning visitors not to feed them, which I thought was terrible until I saw these clean, well-stocked stations throughout the city. Old San Juan takes care of their wild cats: huge bonus points. Puerto Rico-36Puerto Rico-19Puerto Rico-32After finishing the Paseo (there was a rainbow waiting at the end,) I went through the Red Gate to explore the inside of that staggering wall. The San Juan Gate was built in 1635, and dignitaries arriving from Spain or other countries would enter the city through its doors. Entrance to (and exit from) the city was controlled through five gates around the city, but this one was the formal (and most impressive) entrance. I walked through with a one-eared cat on my shoulder.

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I wandered along the colorful cobblestones toward El Morro, one of the walled city’s two forts, which have seen an equally colorful history of wars and rulers under three different flags: Spain’s, Puerto Rico’s, and, finally, that of the United States. As the gateway to the Caribbean, Puerto Rico has always been a key strategic spot, which is why it was so highly desirable—and so heavily walled and protected.Puerto Rico-31    Puerto Rico-51

If walls could only talk… 

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I’d love to hear the stories that the old walls of San Juan’s two forts, El Morro and San Cristobal, could tell. They’re worth seeing, if only to appreciate the historic architecture, gorgeous views, and the lighthouse at San Cristobal. If you’re lucky, you might even get to see a mystical dragon (aka an iguana) like this beautiful creature who had climbed all the way up to the tippity top of the wall to keep an eye on things.
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Although the vibrant streets of Old San Juan are overflowing with quaint cafes, spectacular dining options, and shops of every flavor, my favorite part, as usual, was simply wandering the streets and allowing myself to be enveloped in the magic that was so reminiscent of other favorite places I’ve visited, and yet also uniquely its own. Sophisticated, while somehow remaining whimsical. Each cobblestone, painted wall, and sunlit alley breathes a kaleidoscope of colors that surround and entrance… it’s like a splash of the subtle allure and charm of a coastal town in Spain, right in the middle of the Caribbean. That’s the magic of Old San Juan, Puerto Rico.  Puerto Rico-85


If you plan to walk the Paseo del Morro, keep in mind that the sun gets hot fast and there is no shade along the path. I’d recommend getting an early start, wearing a hat and plenty of sunscreen, and carrying water with you!

Entrance to the forts (Castillo San Cristobal and El Morro) is $5, but it allows access to both for a a few days so be sure to keep your receipt! Entrance is good for a few days, but it is easy to see both in the same day if you choose. *A little helpful hint if you’re a female visiting the forts ~ they are extremely windy. You might want to avoid wearing a short skirt or dress. I probably wouldn’t have noticed as much if I hadn’t been wearing a little sundress… 

If you’ve rented a car, don’t bother trying to drive into Old San Juan — the streets are narrow and mostly one-way, and there’s nowhere to park, anyway. Park on the outskirts of the historic area at the Doña Fela Parking Garage (Estacionamiento Doña Fela) — it’s extremely cheap, and within walking distance to everything.

There is a free shuttle that circles Old San Juan, and if you are short on time or tired of walking, you can catch a ride to the popular tourist destinations, or just stay on for a “driving” tour of the city. But if you’re up to it, walk! That way, you don’t miss any of the magic of the old city’s charm… And, nothing is really that far apart, anyway (including both forts on either end.)

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