Itinerary Ideas: Caribbean Island Hopping (Puerto Rico)

By Lynna - February 25, 2018

If I had to pick only one trip that I would relive over again in a heartbeat, it would hands down be my trip to the Caribbean islands -- it was chock full of misadventures and hilarious shenanigans and moments so beautiful and poignant there are no words to describe the feelings that overcame us.  There are enough memories from this trip to last a lifetime; needless to say, the islands will always have a piece of my heart, and the ocean will forever be calling me home.

The first island we set foot on was Puerto Rico... a mischievous place full of life and vitality. Come here if you want to relax, chill on the sand, eat incredible food, and party all night!  Not to mention some other hidden gems like majestic ruins steeped in rich history.

I think one of my favorites parts about this trip was that we really didn't have an itinerary planned out, we just kind of had a very loose list of items that we possibly wanted to see, but really nothing was set in stone, everything was kind of up in the air and we didn't have any idea what to expect which was why the trip was full of spontaneity and serendipity which made it so fun.  We didn't come with any expectations at all which was why we were blown out of the water by everything.  We just showed up, ready to receive, and the universe surely delivered!

Day 1 - Ocean Park Beach, Castillo San Felipe del Morro, Old San Juan

After landing, we immediately hopped into a taxi and got dropped off at our Airbnb. The hot humid air that engulfed us as soon as we departed from the air conditioned airport terminal told us we were definitely in the tropics.

We checked into our Airbnb quickly, got ready, and without even having a clue about where we were going to go, we traipsed out the door with only the thought of the beach on our minds.

The oh so colorful streets of San Juan
The first meal of the trip was an incredible Puerto Rican traditional dish - mofongo which is made of fried green plantains with a choice of filling (steak, chicken, seafood, etc.)  We tried it from a tiny mom and pop shop right next door to the Airbnb.  Just absolutely incredible!

Keep the margaritas comin' please!

Delicious mofongo!
 After a delicious lunch, we asked the waitress how to get to the nearest beach and she said it was literally only a block or two from where we were!  How awesome is that?!

Cute wallart photo op!
We walked through the neighborhood, found a couple of cute photo ops along the way, and arrived at Ocean Park Beach few minutes later to be greeted with one incredible view.

The water is just always this crystal and aqua turquoise... and warm like a warm bath.... I was in heaven!!!  It was impossible to leave.  It was official, my love affair with the Caribbean Sea had begun and there was no going back.

After spending a couple hours playing and splashing in the warm waves, we decided to continue exploring the island since we only had this one day and then we'd be hopping onto the next island.  (But no worries, we would be returning to Puerto Rico at the end of our trip for a final hurrah!)

We hailed a cab (or rather, hopped into an Uber) which took us to Old San Juan.

The drive into town was simply intoxicating, we sailed through the warm breeze, right along the seagreen coast.

We were greeted with another surprise as we got dropped off right in front of the Castillo San Felipe del Morro which is a 16th century fort that guards the San Juan Harbor.  We had no idea that these forts even existed so we were completely taken by surprise and in complete awe of this magical place.

View from the castle walls
The energy here is so grand and magnificent, the enormous castle standing tall and imposing over the dramatic cliffs high above the waves crashing down below.  It was the perfect setting for a dramatic historical movie.

Completely enamored by this beautiful fort, we spent the next couple of hours exploring its nooks and crannies and pranced all about the castle grounds, having the time of our lives.

Dancing on castle walls

I felt a bit like Indiana Jones

Glorious sunset over the magnificent fort.
As the golden orange Caribbean sun set over the cerulean waters, we reluctantly left our beloved castle and walked into Old San Juan, falling more and more in love with this city by the minute.  It is so rich with history, culture and character.

We window-shopped a bit, bought a ton of gorgeous gemstones from a hidden spiritual shop that we randomly stumbled upon, and after that, we finally decided we were ready for dinner.

To say that dinner was absolutely delicious would be the understatement of the century. I'll let the photos speak for themselves...

I got a wet burrito and Tiffany got tacos.... All of it was completely mindblowing.
Once our bellies were full and happy and our appetites satiated, we asked a couple of locals where we should go for a fun nightlife scene.

They told us to go to the most famous bar on the island called "La Factoria" which apparently is where all the cool kids hangout at.  Soon enough, we found ourselves in a cab and on our way to this legendary bar.

The entrance was so hidden that we walked by it a few times, but we couldn't help noticing the area which we got dropped off in was practically swarming with young hip groups of people dressed to the nines!  It was definitely the hotspot of town and was so crowded it was almost difficult to walk around at times!

Look how crazy crowded it was!  It looked like this on every single street....insane!
Alas, we found the entrance to La Factoria and went inside .... to be greeted with a cozy intimate room with dim lighting and atmospheric electronic music playing.  We were completely intoxicated with the vibe here.

The reason La Factoria is such a popular place is because there isn't just one large room. but rather a series of doors and doorways that lead you further and further into the building, each leading into a different room.  Overall I believe there are around seven to eight different rooms, all with their own different themes and crowds. Imagine a cozy intimate wine bar in one room, then a door leading to a hip hop dance floor in the next, and the next beyond that, an arcade with a pool table.  It was so cool!  We had a really fun time here and could really get a better gauge of the Puerto Rican way of life.

The intimate wine bar
Exhausted from our highly eventful day, we retired to our Airbnb for the night after a few fun hours mingling and dancing at La Factoria.

This concludes our first day in San Juan, Puerto Rico (it was only the first day and we had already fallen head over heels for this place), but stay tuned for upcoming posts about the rest of our trip!  The very next morning we woke up early to hop on a plane and continue our adventure to the next island!

Island hopping via mini seaplane!!!

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