My Holiday in San Juan, Puerto Rico

I wish I had posted this months ago. The past week, I’ve been heartbroken as I’ve learned of the devastation that has befallen Puerto Rico. While it’s sad to think that much of what I share in pictures below has been irrevocably lost, I feel it’s important to share in the hopes of at least encouraging each of us to keep them in our prayers.

You know it was a good holiday when you smile every time you think back on it!

In sticking with my $1,000 budget, it was down to Cartegena, Bolivia or San Juan, both of which I had not visited or even considered much before.  But with July quickly approaching, I needed to make a decision. Both represented a culture and climate that I was very interested in experiencing, and the lodging was similarly priced. So it was coming down to airfare, which I really needed to be around $500 or less. Finally, at the end of June, I was able to score a flight on AA (my preferred) for $475!

Now it was down to lodging. Normally, I would search for Airbnb with these filters:

  • Entire Place
  • < $100
  • Wifi
  • Kitchen

Then, I would do some research to find the optimal area to stay in to best experience the area on foot. But this trip would be a little different. I wouldn’t be traveling alone. {da da dah!!!}.  I know. I was in shock too! Well in the past year I’ve been blessed with a wonderful girlfriend who, while “totally ok” with me going alone, convinced me this would be a good opportunity to see if we could stand 5 days together on an island. knowing what’s good for me, I agreed. So, (being not married), I changed my filter to < $200 and a 2br/2b arrangement.

Next was deciding on a location. One of the benefits Airbnb affords is that you can find places that immerse you in the daily life of the local people, which is something I enjoy. Still, there was a decision to be made: stay near the beach or in the “Old San Juan” area. Both had their plusses and very few minuses. What is came down to was simply the idea that being near the beach would require taking an Uber or public transportation to visit OSJ. And while sun & surf were on our To Do list, we really looked forward to exploring the history of the city and its people.

That meant we still had about 25 places to choose from, all between $75-$175/nt, a nice problem to have! So the next few weeks were spent reading reviews, going through the posted pictures of the homes, and using my awesome Google Map skills to visually pinpoint where each place was – very handy when you’re thinking about what the walkaround experience will be like.

The place we ultimately chose was exactly what we’d hoped for, situated in the heart of OSJ, with both a balcony and a patio. Despite the fact that Airbnb doesn’t provide you the address until after 


purchase (for security reasons), I was able to find it by using Google Streetview and basically ‘walking’ the general area, looking for clues based on the exterior photos. I cut it close, with just 2 weeks to spare! #geek

Airfare and lodging squared away, I ‘lightly’ put together an itinerary of restaurants, sites, and activities, with the only real commitment being to spend at least one day at the beach. Other than that, each day would be an adventure unto itself – the best way for me to be relaxed on holiday.

The flight was early morning (6am) with a short layover in Miami, but with an empty seat between us it was really easy to spread out and relax. It also meant that we were able to get to our villa by 4pm, so there was still plenty of day left for us to enjoy after getting unpacked.

What struck me most about San Juan was that, while it is a U.S. Territory, you feel worlds away from the U.S. mainland. From the vibrant colors and styles of the local architecture, to the people and prominence of Spanish speech, it can very easily confuse you into wondering whether you need to keep your passport handy (you don’t). Also, it can’t be stressed enough how clean and safe it is. Particularly the parks and historical sites, you didn’t see the typical littering you find in stateside, which made it very welcoming to while away time sitting on the lawns or strolling the streets late in the evening.

Food. Oh my, the food! From the first evening to the last afternoon, save for a couple of personal failures (Wendy’s and Starbucks, natch), we ate or meals at local restaurants and thoroughly enjoyed ourselves. My vote for “Best Dish with the Sketchiest Name” has to go to the local dish called Mofongo, which is mashed fried green plantain, seasoned with garlic and spices. You select your choice of protein (mine was skirt steak) and then serve it piled high. After seeing others dine on it for a few days, I finally enjoyed it myself at Barrachina, a very nice restaurant that also happens to be the birthplace of the Pina Colada. We didn’t confirm. My girlfriend was just as adventurous and was duly rewarded with the best fish tacos she’s had on several occasions. I also want to call out Casa Cortes Chocbar, the only place we at ate twice because they had a really great breakfast. And chocolate. Lots of chocolate.

The proud history of San Juan, which is on the northeastern coast of San Juan, is very evident, displayed most prominantly by the two forts and wall that surrounds most of what is now called Old San Juan. For the incredible price of $5 per person, you have 7 days to explore both forts at your leisure. And because they assume the best of tourists, there are very few barriers to experiencing the magnitude of the fort itself. You can literally walk up to the edge in many places and casually fall over the wall, plummeting 50ft or more to your death. It makes for great photos, but you might want to keep a close eye on your kids.

There are several really great beaches in the San Juan area, that is for certain. But I really wasn’t looking forward to spending a few hours with 100s of others, vying for both real estate and a calming experience. Our housekeeper shared with us that there is a beach behind the capital, about a 15 minute walk from our house. There, we found a really nice area with about a dozen people spread over a good 1/2 mile of shore. It was fantastic!

I’m sorry it has taken so long to write this, and deeply saddened that the Puerto Rico I fell in love with has been so badly affected by both Mother Nature and the Trump Administration. Yet, I know that the heart of Puerto Rico will strengthen the people through this difficult time, and I look forward to returning to once again be among some of the best people.

Footnote: There are many, many well intentioned organizations out there for you to support. I will suggest one, One America Appeal which, with the support of former US Presidents, helps our fellow citizens in Texas, Florida and the Caribbean as they recover and rebuild. 

The government of Puerto Rico has also launched a guide that details how individuals or companies can donate emergency and construction supplies (from bottled water, hand sanitizer and formula to extension cords, tarp and safety glasses). The National Voluntary Organizations Active in Disasters (VOAD) is coordinating many of these donations here (and corporate giving here).