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).

Costa Rica

“The best adventures, if you just let them be, are the unplanned ones.”

After experiencing Prague earlier this year, my intention was to go to San Juan, P.R. in late summer. But when I learned that my oldest would be studying abroad in Costa Rica, I did a little research (like, 5 minutes) and added San Jose, Costa Rica to my Hopper watch list. That’s pretty much all I did in terms of planning 🙂

In June I was able to grab a $370 roundup trip ticket on American Airlines, my preferred carrier. Not bad, right? Extending a layover can be an inexpensive way to get bonus time on a holiday. On my excursion to Prague, I was able to take a walking tour of Berlin and a leisurely afternoon people watching from a coffee shop near Piccadilly Square in London. On this trip, AA offered Dallas or Miami as waypoints. I chose Miami both ways, 6hrs on the way out, and overnight on the way back.

I’m very committed to “no stress travel”, and it almost cost me this trip. Almost. Because upon my leisurely arrival to the airport, about 1hr before departure time, I was informed that I’d missed the cutoff for checking in my luggage, and would either have to do carryon or take a later flight. With a long layover in Miami I really didn’t want to be dragging a suitcase around, but I also knew it was too large to go in the overhead bins. What to do? Well, I recalled from seat selection online that the flight was fully booked, and so I pulled my trunk through security, making a very experienced bet that they would offer free bag checks at the gate. And they did. Phew. I was already $25 ahead on this trip!

While my arrival in Miami was uneventful, there are two observations I’m going to make that apply to many US cities. 1) too often, the directional signs seem to assume you step off your flight and have some level of familiarity with the airport. What would really help is a simple sign when debarking the jetway that would simply tell you what Terminal, Gate, Level, etc. you are on. I spent way too much time just locating the Shuttle/Pickup area. 2) While I hate the asthetics, front license plates are really, really helpful when you’re looking for your Uber. Ok.

With the temperature expected to be in the 90s and humid, I did not relish sitting outside all afternoon in Miami, so I took a chance and Uber’d to the hotel I would be staying at on my return, the Hotel Cadillac by Courtyard on Miami Beach, figuring I could hang out in the lobby or poolside. If I were to be asked if I was staying there, I was sure t
hey would understand and consider the fact that I would be a guest 5 days later. It never came up, so I was able to relax in comfort there and at the little market/sandwich shop across the street. Given the early hour that I’d left, it was a nice respite before the 3hr flight into San Jose.

Now, Barcelona is one of my favorite travel memories, and so I was looking forward to a similar climate and possibly culture. I did begin to do a little more reading on Trip Advisor, Wikipedia, if only to get a sense of the climate, tourism, history, and economy. What I discovered was that I would be experiencing a very traditional Spanish city with a very proud a vibrant heritage, good food, and a busy urban city. While I considered staying on the outskirts, in the hopes of spending some time with my son on his arrival, I decided to stay in the city. Next time.

After a great Airbnb experience in Prague, I was set on the same type of lodging. And while there were some beautiful condos available for $75-100/nt or less, I decided to leverage my Expedia points and see what I could get. So, sadly, no penthouse suite for me. Instead, I ‘settled’ for the Park Inn by Radison, where a 4nt stay only cost me $270! I made a point of contacting the hotel on their Facebook page before my trip, and was pleasantly surprised to get a

response back from the Manager, welcoming me. While I can’t say for sure the upgrade to a King Executive (from 2 Qns) was a direct result, I was both pleasantly surprised and appreciative.The hotel is relatively new, spotless, and only a 5 minute walk from the main streets of the city. A free breakfast buffet each morning is a great start, with a nice assortment of eggs, meats, beans & rice, pastries, fruit, and cereal. Most of all, the staff was always helpful, smiling; it’s something I will always remember when I think back on my stay there.

I’ve learned that the best way to experience a city is with your own two feet – I walked 5 miles on average each day, with no
real agenda but a fairly good idea of where I was, interesting sites to look out for, and (most importantly) a general idea of how to get back to the hotel. As with Prague, people watching and exploring the various markets, alleyways and
random events was exactly what I’d hoped it would be. But I was surprised to discover that English is not spoken commonly nor found on much signage, and that made for some interesting attempts at conversation. I finally resorted to using Google Translate to see the phrase I was attempting and then verbalizing it, and that helped. Still, I will make a point of having a small vocabulary next time.

Food. Because I was in the city, there were many of the US fast food restaurants available, which I shunned. I did find the one and only Starbucks
, but I consider that more of a mecca, and therefore felt obligated to attend service there. It was kinda odd though, that even though it looked like every other ‘bucks, there too English was not spoken. But I survived, because Americano is universally reckognized. I enjoyed shrimp and that was fantastic.
Beans, rice, pork and chicken in some fashion was enjoyed every day and I loved it. The Central Market had several food stalls to choose from, and so I through caution to the wind (but not my Immodium or Pepto-Bismol) and partook with no side effects.

I did decide to try and do one ‘activity’, and that was ziplining, with tours that would take you into the jungle for what would be 2-2 1/2 hours of zipping through the forest. Sadly, because of the rain they were experiencing and the fact that I wasn’t willing to pay double because I was traveling alone, it didn’t work out. A little disappointed, but again, I’m in Costa Rica on holiday. Perspective 🙂

As I m
entioned earlier, I decided on an overnight layover in Miami on my return. Partly because I wanted a slower acclimation back to life, but mostly because I could. The Zika virus seemed to have impacted tourism a bit, because there were many good and economical choices near the airport, figuring I could take an Uber to the beach. On a lark, I decided to dust off my Marriott account and discovered that I had enough points there to stay on Miami Beach. The oceanfront room was fantastic, as was the experience of being able to just relax on the beach and really thank God for a great holiday time. All together, the trip was way under my budget, but provided the time for reflection, relaxation, and new experiences that I really look forward to.



Starwood Hotels Disappoints, Mocking My Loyalty

Maybe I’m just tired from working too long hours, in too many cities lately.  But take a look at this web page below and tell me what you think:


I think this says:

  1. Your award nights are given for eligible stay dates between 04/30/2009 and 09/27/2009
  2. Your award nights have to be used between 04/30/2009 and 09/27/2009

Well, guess which one Starwood thinks it means?  #2, of course.  Which I learn tonight when booking some time away for the family.  Grrr.

For spending 50+ nights a year at Starwood hotels, is this how they treat their Platinum members?  Creating a personalized website that can be be misinterpreted? 

So, I called the Platinum Customer Service Desk (ooooh!).  They politely reminded me that the Terms & Conditions “…clearly spelled out that the days had to be used by 09/27/2009…”  Of course, when I explained that I never got a copy of the T&Cs, the representative offered to find a copy and send me the link.  10 minutes later she found it.  Which proved my point – they never expect members to read them, and don’t make them easily found.  At the very least, they could have link the relevant T&Cs to each of the Award Descriptions the member was eligible for, would have taken less than an hour to set that up programmatically.  And don’t get me started on how someone would book by 09/27/2009 and stay 09/27/2009.

I’ve got more than enough points, but was looking forward to using this reward and keeping the points for our bi-annual Disney World trip, maybe a few other excursions.  I’m just upset, and slightly peeved that I got suckered into heaping platitudes on this company, only to find that they may not be as loyal to me as I am to them.

I’m writing them an old fashioned letter now, even left an email with their Customer Service department.  Surely someone there will realize that a) they could have done a much better job of explaining the award rules, and b) this isn’t worth losing an extremely loyal (and lucrative) customer over.

But just in case, I think I’ll dust off my Hilton membership card.  Because I despise bad customer service and don’t tolerate stupid policies either.