San Juan, Puerto Rico: Even Better The Second Time Around

You know, you may not be born in Puerto Rico, but Puerto Rican is definitely born in you.
— Rosie Perez

Once upon a time after an argument with the then apple of her eye, a young lady was eager for an adventure and decided to go on a 10-day trek to 7 different islands for her first international (and solo) adventure.  While on that trip, she managed to squeeze in some time to Puerto Rico, a place she had been hearing about for as long as she could remember, but had never visited. Once there, she enjoyed every ounce of her time there but only had about 60 hours in the country and nonetheless felt a bit cheated.  The young woman vowed that she would return again.  18 months later, she did.

I had quite a bit of mess leading up to my favorite holiday, New Year’s Eve, and I was not too thrilled about it.  Sometimes, when it rains it pours, and that was definitely my December.  My Aunt Agnes and Uncle Newton (married) passed 19 days within one another, I was sick, and still recovering from my shoulder injury from the last trip.  From the outside in, I can totally understand why someone might have looked at me like I was crazy when I said I wanted to get away for a few days so that I could breathe.  I was under some silly impression that I would be able to punch out a lot of blog content while visiting my family in New Jersey, but I wasn’t in the correct mind space and to be honest, I’m not upset about that because I was more present with my family.  However, it was time for a break and for me to just get some quiet time before I finally returned back to work.  I went back and forth about where I would go.  I wanted to knock down country number 18 for the beginning of the year but when I did cost comparisons, I kept looking back to Puerto Rico.  Yes, I had already been there and yes, I wanted to be in a new location but I truly did enjoy San Juan.  When I saw how cheap the flight would be from Miami on New Year’s Day, I knew I better had just go ahead and book the flight before the price skyrocketed back up.

Related Post: 3 Reasons Why I Am No Longer Against Repeat Countries

My Less Than Ideal ReIntroduction Into Puerto Rico

When I landed at San Juan’s airport, I rushed to an airport bar to see if they were showing the Cowboys game against the Eagles, and they were!  I sipped an overly expensive margarita as I cheered on America’s team, but decided that I really wanted to capture the sunset and needed to get to my hotel fast.  After discovering that it is against San Juan law for hotels to provide airport shuttles, I rushed to the taxi stand and found myself en route to one of my most favorite cities from my travels.

Now, most of you know that I really enjoy hostels.  I love the community vibe, the people I meet, and how cheap it is.  However, because I was so mentally drained, I did something I had never done in my travels and decided that I would stay in a hotel during my entire stay in Puerto Rico.  I wanted to relax, be alone, and roll around in a queen bed instead of a twin.  I was excited because after reading the reviews on Hotel Tonight, I selected a hotel with a gorgeous rooftop pool and view right in the middle of Old San Juan.  I was geeked up about the decor and was looking forward to sipping a sangria at sunset.  Unfortunately, everything you envision on your travels does not come to fruition.

After arriving at my first (yes, first) hotel after being in traffic for about an hour causing me to miss the remainder of my game, I was looking forward to a few moments of relaxation prior to chasing the sunset.  Imagine my surprise when I heard, “Oh, Ms. Cross-Johnson, no one reached out to you? We just called you.  There is an issue with…” and internally I begin to go red but I try to #KeepCalm.  Apparently, the lock on my [paid and reserved] room was broken and it would not be able to be fixed prior to my arrival.  I was irritated because checkout was hours prior so why was this hotel just noticing the issue and only reaching out to me at 4:30 when check-in started hours ago.  Thankfully, the great people at HotelTonight helped me resolve the issue with that inhospitable hotel and I was actually blessed with a discount and a better location just a few blocks down the street.  I think that was Big Homie for rewarding me for keeping my attitude in check.

Vacation Mode: All The Way Turned Up

For those of you who have been following my blog since the beginning, you know that I typically book my lodging with AirBNBs and hostels.  If I choose a hotel, it is for one night only but because I was in dire need of relaxation, I wanted to be on chill for all four evenings.  I chose to stay in Old San Juan for two nights and Condado Beach for the latter two.  So, after checking into the hotel I rushed upstairs because I was determined to capture the sunset every day I was in Puerto Rico.  The view was totally worth it and as I was upstairs I heard some music and people celebrating around the corner.  Being as it was still New Year’s Day, I opted out of the nap I had planned on taking and decided to check it out.  I walked towards the cathedral and the plaza and witnessed people singing on the stairs, the street, and in a parade of sorts.  I don’t know what everyone was singing, but it was pretty dope to see a random assortment of people come together and keep moving in the holiday spirit.  I was happy to be back in a city that brought me such joy and the fact that it was a holiday was just icing on the cake.  

I had been doing a bit of research for some new restaurants to try out in Old San Juan as well as checking to see if my favorites from my first trip had been open.  I had some non-negotiables and also wanted to check out some Puerto Rican dishes like pernil and mofongo.  In addition, since it was still technically Winter, I wanted to knock down as many glasses of coquito as possible. When I tell you all that I ATE and ate WELL in Puerto Rico, I did.  I was not concerned about how I would look in a crop top or my bikini because I was quite full and happy and since I was on a solo vacation, I did not have a soul to answer to.  

Food & Liquor Runs In San Juan:


Adding a Bit of New With The Old.

I enjoy exploring new places and getting lost, but I must admit that I had a calmness about me because of the familiarity I felt with Old San Juan.  I remembered the streets, the names of landmarks, and where I enjoyed my time the most.  I knew I could walk around the entire span of OSJ and be relatively safe.  I also had enough Spanish under my belt to be able to move around if I encountered someone who did not understand English.  

I was so enamored with Old San Juan when I visited Puerto Rico the first time, I did not step foot on the beach which is extremely rare for me.  I am usually running towards the sand first, but I loved the culture of the old city and that was where I stayed.  This second time around, I wanted to be by the beach and get some time in with the water and observe the sunrise / sunsets up close.  I was worried that Condado was going to be overpriced and super touristy, but it wasn’t.  Perhaps I was visiting San Juan during a low season, but at times the streets were quiet and I enjoyed slowing my pace down.  The beaches had some rocky areas but the water was so warm, I did not mind.  I spent some quality time reading a new book and just writing in my journal.  It was what I needed as I was coming to terms with everything going on back home and attempting to mentally prepare myself to head back to work for the first time after almost a month.  

I was happy that I added in a separate hotel stay at Condado because I was able to see areas of San Juan I had not seen before.  I saw more street art, authentic eateries, and a continuation of the Puerto Rican’s love for tiles.  I could walk up and down the street smelling salt water and feel the breeze that I couldn’t capture in the walled neighborhoods of Old San Juan.  I was able to watch cruise ships come in and airplanes take off.  I was not always pushing and prodding my way through the streets because the Condado was not as inhabited.

What made the second time around better?

Overall, I think that San Juan is just a super FUN city to be in.  Puerto Rico is sexy and you cannot help but feel the pulse of the island and want to get up and salsa at the lounges (which I embarrassingly attempted to do).   I ran into a friend from college (Go ‘Canes) and we were able to eat, drink, and get caught in a pop-up storm.  The shopping was still great and my favorite place ever, The Poet’s Passage is where I could grab a cup of coquito and read poetry.  

I walked with my head higher because I was in familiar territory and felt like I dived in a bit deeper.  I think that everyone should have a special place that they retreat to for a quick recharge (this does not have to be an international destination either).  I was in the same city, but I had a different experience.  I knew what I wanted to see the second time around and had fun moving at a slower pace because I did not feel as rushed as I did during my first visit.  Sure, there were still some things I did not do but I am not worried because Lord willing, it will be there waiting on me for when I come back (third time’s a charm right?).  

Have you ever been to Puerto Rico?  What did you enjoy about it?  What’s your favorite destination that you retreat to? I am always looking for suggestions so talk to me!