The ‘Roady just got back from a weekend of fun and sun in the U.S. territory of Puerto Rico and I’ll be spreading out the tale over at least a couple posts here.

Breeah and I arrived last Friday afternoon and had enough time to take in the beach, food and Isla Verde avenue before settling in. Our hotel of choice? The InterContinental in Isla Verde – a throwback-style resort that was probably my last choice two months ago but comes highly recommended after spending a weekend there. The catch – we hit P.R. right in the offseason (I’m always surprised there is an offseason in these parts of the world) and Priceline gave us an unreal $82/night deal (high season apparently throws the rate to AT LEAST triple that…)

'La Rogativa' sculpture, a comfy bed for a cat...

The difference between my stay at the InterContinental and Melia Caribe Tropical in Punta Cana, D.R. a couple months ago was apparent from the outset. I didn’t get hassled for timeshares (only once was offered a room upgrade and wasn’t bullied after a polite denial) and we were right smack dab in the middle of a Caribbean metropolis – with old school hotels towering above the beach and a character of the place that hasn’t changed much in 50 years (see: The Rum Diary this weekend in theaters for compare) but has Americanized while staying true to the local flavor (fast food stores and Walgreen’s abound, but don’t necessarily feel out of place).

Breeah in front of Banco Popular in Old San Juan

Oh – let me get one more thing out of the way before I dive into our Saturday activities. I decided to rent a car for this adventure (I am the Roady after all) – but was met with dire warnings about driving in and around San Juan and especially Old San Juan. OK, maybe it was because it was offseason – but the driving around here, while erratic and aggressive at times is not much more (if any more) of a challenge than driving in D.C. (or any other Northeast Corridor metro area for that matter). There were a couple instances of red lights being run, drivers forcing themselves into lanes to make illegal left turns and nearly no signaling, but I never felt unsafe or not in control. Take it for what it is, but if you’ve experienced enough difficult driving conditions on the mainland, then you should be experienced enough to drive on the Isla del Encanto.

A beautiful side street with inviting shade, also home to a lot of...

We decided to hit Old San Juan early and beat the tourist jam-up (if there was going to be one). Outside of the 5-minute drive to the hotel on Friday (p.s. DO NOT USE GPS data from Google Maps on a Garmin, it may get you to the vicinity, but I spent about 20 minutes on the right street going the wrong direction looking for the hotel) this was our first real island driving experience (ok, we drove on Price Edward Island earlier this year…, far different than this). The drive really takes you back to a 1970’s Miami postcard skyline. Then you get tossed right into the 16th century as you make your way into Old San Juan, waves crashing on the shores to the right and ancient city walls and fortresses welcoming you to one of the oldest European-established cities in the Americas (and the oldest under U.S. jurisdiction). The transition from the smooth highway to one-way cobblestone road is almost immediate and – thankfully – my trusty Garmin led us right to the parking lots on Recinto Sur (Tip – we took the first parking lot, which is a bit more pricey than the second one as it is attached to the nearby Sheraton, but it seemed to be more spacious and less of a hassle than the one further down the street).


I was somewhat surprised we made it into the old town with so much ease, but here we were, at the heat of the morning (and it was hot! As I found out throughout the trip, the morning sun beats down here, it actually gets cooler as the tradewinds pick up later in the day).

The wall around the old city is huge!

You’re immediately transplanted into the pastel poetry of Old San Juan the moment your feet hit the ground here. It’s a constant kaleidoscope of reds, baby blues, pinks, yellows, greens and purples. It’s magical. It’s something you don’t see every day on this side of the world. This a colonial city in the U.S. – it’s very bizarre. The only thing that kept reminding me that I was still in my country was the majority of tourists being from mainland U.S. (and the Burger Kings of course).

Pink before pink was cool...the Casa Rosa

I’ve never been so excited to visit a part of any city in the U.S. as I was with Old San Juan. I’ve over-read reviews, travel guides and seen episodes of Man vs. Food and Ghost Hunters filmed here, but those only served to heighten my curiosity – not spoil the fun. Believe the guidebooks, my fellow roadies, Old San Juan lives up the hype – if only to walk around the ancient walled city and take in the colors, the music, the food and the general ambiance of a city with many tales to tell.

El Morro and the Morro Esplanade

The shops – working on island time, it’s very rare you see posted hours anywhere – hadn’t quite opened for the day and the foot traffic was sparse, so we made our way up to Parque de las Palomas where we saw our first views of the San Juan Harbor – with the Central Mountains making up the view to the right and El Yunque towering above the San Juan city skyline on the left. Pigeon-like birds were out in full force as we turned up onto Cristo Street (one of the main drags of the town). Cats also rule the roost here, and were nestled up on ledges, monuments or crawling around streets and sidewalks at their leisure.

The Magadelena Cemetery looms just outside the fort's wall

The city is essentially walled in – as the old forts of El Morro and San Cristobal dominate the coastline – similar walls to those of the forts also protect the harbor. In a way this protection could draw comparisons to the Vatican City or other “walled-in cities” and gives the feeling that you truly are in a protected, exclusive place, even though the iconic garitas (a symbol that the Puerto Ricans use on their main license plate) that dot the walls and fort are unmanned in the present day.

A garita overlooking the ocean

We walked past the Casa Rosa – its pink colors piercing through the greens and greys alone on the northwwestern side of the city. This building – a former barracks turned day care center – hardly looks 200 years old.

We winded our way back into town and up Del Morro street, and there it was – Fort San Felipe del Morro (more commonly  known as “El Morro” – one of the most recognizable forts in the western hemisphere, if not the world). Here the Spanish set up shop for some 350 or so odd years, holding strong against various pirate and colonial attacks. It’s an imposing structure for anyone hoping to enter the harbor and cause a ruckus. The fort juts out at the extreme Northwestern neck of San Juan island and seems to be one with the landscape as the rocky coast merges seamlessly with the ancient, ocean-worn stones of El Morro.

Inside El Morro

Today the ravages of war have given way to a beautiful recreation area, the Morro Esplanade (or Explanada del Morro). Families from the mainland and Puerto Rico alike were out picnicking and flying kites. It’s a beautiful walk on the grass to the fort and Breeah and I couldn’t have asked for a more beautiful day to roam these historic grounds.

The world's most eye-appealing slum...La Perla

This visit also knocked a rather tough-to-get National Park Service site off my list as well. It is the only NPS-protected site in Puerto Rico, which encompasses both forts (San Cristobal being the other) as well as El Canuelo (a small fort and old leper colony located across the bay) and most of the walls of the old city. No worries for english-speaking visitors – a visit to these forts will just like any park service site on the mainland (except for architecture). Signs are in both English and Spanish and park rangers dressed in familiar garb speak very good English.

A view from the northside of town down the narrow roadway

I will admit Breeah and I were both far more fascinated with the photo opportunities the fort provided (not just of itself but the surrounding coastal views and that of La Perla – more on that in a sec). However, we did take the time to view a 10-minute movie and read most of the signs we stumbled across.

A view of El Morro and La Perla from a San Cristobal bunker

As noted above, the views of La Perla are extraordinary. La Perla (“The Pearl”) is a squatter-town, nestled right on the coast just outside of the gates of Old San Juan (and literally huddled up right next to the Santa Maria Magdalena de Pazzies Cemetery) and squeezed in between the two fortresses. It’s accessible – if you dare. However, I feel this drug slum is likely over-hyped for it’s dangers and has become more legendary for this image than it likely is. That said, it is what it is and for Joe Tourist – like you and me – I chose to stay inside the wall and enjoy the colorful houses perched along the rocks from a distance. The police were on patrol, likely warding off tourists accidentally (or purposely) wandering in. We saw one car full of stateside tourists go in and, no less than 20 seconds later, drive back out the same way.

The skyline of San Juan

We walked the northside of town (via the picturesque Plaza Del Quinto Centario) looking for food and found La Tortuga – a fun little pub and eatery that served up a great pizza (very similar to the thin crust, yummy sauce style of pie that Grotto Pizza serves in Delaware). Our waiter was more than friendly and when the food was taking awhile to prepare he came over to set our table, saying “It will be right out, believe me, I am good to my people. We’re no rush here, right?” The laid back and cool atmosphere (with flat screens tuned to ESPN) and amazing food (and pina coladas) gives this place a big thumbs up – even though it’s mysteriously missing from most guides I’d studied up on.

and the skyline of Old San Juan

After chowing down we headed out to Fort San Cristobal, the second and newest of the two forts. The walk through this area of the old town has a different character than that nearer to port. It’s quieter and mostly consists of various apartments. A statue of Abraham Lincoln at a school named for him completely caught me off guard (we didn’t know it was Lincoln for sure until we saw the name of the school). We headed up to the main boulevard by the coast (directly behind La Perla) and entered San Cristobal.

Each street has it's own flavor

San Cristobal was more or less created to protect the city from land attacks once or if El Morro couldn’t do enough to protect the waters. In it’s 220-odd years it was featured in two major attacks – one from the British (in 1797 – just ten years after completion) and, of course, in the Spanish-American War of 1898, the battle that eventually ended in Puerto Rico becoming a U.S. Territory).

A "hotel" near the San Juan Bautista Cathedral

San Cristobal keeps the same flavor as El Morro and is built in generally the same manner – but the courtyard and interiors borrow more from Romanticism – something you don’t see at El Morro – which is a straight up post-Renaissance fortress. Cristobal is definitely not as “gritty” as El Morro and provides better views of – you guessed it – the city proper and old town alike (which explains its location for land based attacks, despite it also hugging the coast).

Smallest row house ever?

At $5 per person, snatch up the two-fort pass. For one week (if you wish to visit San Juan multiple times on your stay) you can see both forts. While San Cristobal seemingly plays second fiddle to El Morro, both forts are worth seeing for the views alone and both bring plenty of history to the table.

The tomb of Juan Ponce de Leon

We ended our day in Old San Juan back on the main roads. The crowds were in full force as the afternoon came but we managed to pick up some tasty pastries from the highly recommended La Bombonera (as seen on The Food Network) and souvenirs from one of the many affordable shops lining the San Francisco street. We weaved our way back to the El Convento hotel (where we strayed towards Casa Rosa earlier) and entered the Cathedral of San Juan Bautista – the second oldest cathedral in the Americas and the final resting place of one Juan Ponce de Leon.

A storm looms...

The beautiful day quickly turned into a late afternoon rain shower. The clouds that once loomed over the mountains had made their way north. We jetted out of Old San Juan via the harbor road and averted a flash flood that nearly blocked off the other side of PR-1, causing a huge jam-up that we happily weren’t apart of. We hit up a trendy little tourist-friendly Mexican place called Lupis – owned by former New York Yankee pitcher Ed Figueroa (who adorned the outside wall of his restaurant with photos of past Puerto Rican baseball greats). The must-have fried ice cream is unreal.

Maybe this is what they meant by nightmarish traffic jams...flash flood!

Old San Juan is truly a priceless treat that is worth the price of admission into Puerto Rico alone. But we weren’t done – a full second day was looming and we had plans to tackle the jungle, namely El Yunque!

For more photos from this day, check out my outtake gallery on flickr.

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