Guest Post: Exploring The Caribbean Without Leaving the US in San Juan

About the Guest Author - Kailyn

Hi! I’m Kailyn and I have the privilege of being Kevin’s cousin. We’re only six months apart in age, so we were really close growing up. Now that we’re older and live in different countries (I live in Chicago) a shared love of travelling helps keep us close.

Update January 2020: I now have my own travel blog called Kailyn Travels! Check it out here!

My boyfriend, Andrew, and I at a Cubs game!

Kevin and I have traveled together a few times already: I visited Mexico City with him before he moved there, Kevin has visited me and Andrew in Chicago, and we’re planning an upcoming trip together this winter.

Kevin and I visiting Teotihuacan in January 2018

Puerto Rico

My boyfriend and I visited Puerto Rico for a long weekend over Labor Day and had the best time! We stayed for three nights, but I left feeling like there is still so much to see and do that I want to return, hopefully in the next year or two!

We had amazing food and drinks, drove through a rainforest, went snorkeling at a beach that is ranked as one of the most beautiful in the world, and explored Viejo (Old) San Juan. I will cover all of that and more in the following blog post as I hope to inspire all of you to visit Puerto Rico!

Viejo San Juan


If there is one thing Viejo San Juan is most famous for, it’s the architecture. All the houses and buildings have the original historic facades from the 1800s and are painted in such bright and beautiful colors.

One of many beautiful streets close to our Airbnb

If you have an extra hour or two, it’s fun to just wander around all the streets to see as much of Viejo San Juan as you can, which is definitely doable as it’s a very small and walkable area.

Paseo del Morro

There is a wall built around Viejo San Juan that was constructed in the 16th and 17th centuries to defend San Juan. We took a one mile walk around the wall and ended at Castillo San Felipe Del Morro.

The Red Gate was one of the original entrances to the city.

The walk can be brutally hot as there is no shade, but at the end of the walk you will end up with this amazing view.

View of the north side of Viejo San Juan from the Castillo
The Paseo del Morro is filled with many stray cats, how many can you spot?

El Yunque

We took a day trip to El Yunque National Forest, which is about a 45-minute drive from San Juan. I looked into bus options from San Juan but didn’t really find any, so we decided to rent a car, which was only $50 for the whole day including insurance and fees. The drive is pretty easy and there are signs for El Yunque at every turn you need to make.

La Coca Falls

Sadly, only a small portion of the park is open, due to severe damage caused by Hurricane Maria in September of 2017. Currently there is only one waterfall open, a lookout tower with amazing views, and one trail. Hopefully they continue to make progress and reopen more of the park. One of the main reasons I want to come back to Puerto Rico is to see more of El Yunque.

Yokahú Tower

The Angelito Trail is only a half mile long one way, so a mile round trip. Once you get to the first creek there is a sign that says the trail ends there, as the bridge was washed out by the hurricane. We saw many people crossing the creek anyway, so we decided to follow suit! Fortunately, there are many large rocks in the creek and it is easy to get across without getting wet.

A few hundred yards after the first creek you will come to a river with the most beautiful swimming hole with a rope swing and all. If you come on a nice day, plan on staying for an hour or two to enjoy the refreshing and clear water!

Finding this swimming hole was such a nice surprise!
Andrew having fun on the rope swing!


Wow, it is so hard to put the beauty of this small island off the east coast of Puerto Rico into words! The highlight of the trip for me was undoubtedly visiting one of the most beautiful beaches in the world according to multiple travel guides, Flamenco Beach on Culebra Island. I booked a day trip through East Island Excursions and I would highly recommend them.

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brb, applying to jobs in PR

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The trip sets sail out of Fajardo which is about an hour drive east of San Juan. You have the option of being picked up and dropped off, or driving yourself.

Our tour was on the Caribe Spirit, a high speed catamaran, and it took about 40 minutes to reach Flamenco beach where they anchored out by the reefs. They set up a deli lunch and began serving rum drinks. The food and rum are included in the price of the ticket.

The darker areas in the water closer to shore are the coral reefs we snorkeled over.

After you eat, you can take your flippers and the snorkel mask they provide and hit the reefs! I spent about an hour snorkeling and exploring. I was able to get so close to the reefs as some of them are only a few feet below the surface of the water. A few times I was almost scared by how close I was as I swam over!

After snorkeling, they move the boat a few hundred yards closer to the beach and you get to spend the last few hours of the trip relaxing on the beach and drinking rum.

Food and Drink


The most famous dish to come out of Puerto Rico is called Mofongo. Mofongo is made from unripened plantains that are fried, then mashed together. It is then stuffed and topped with your choice of meat. I sampled it from two different restaurants, Punto de Vista Rooftop, and Los Yeyos.

Mofongo with fried pork and garlic sauce from Punto de Vista

Punto de Vista Rooftop is one of the top rated restaurants on Yelp, which is how I found it. It was delicious and I would definitely recommend it, although there will probably be a wait during popular dining hours. My boyfriend and I shared the Mofongo with fried pork and shrimp with garlic sauce; I recommend both!

Kioskos de Luquillo

After leaving El Yunque, we wanted to make the most out of the rental car we had for the day so instead of heading west back to San Juan we headed east to check out Fajardo. 

On the way there we spotted a crowded area right along Route 3 nested between the highway and Luquillo Beach, and decided to stop in. There are a long row of little shacks all crammed in right next to one another mainly selling fried food and alcohol.

Unfortunately I didn’t snap any pictures, but we had a few seafood empanadas, took a walk on the beach, and continued back to San Juan.


On our last half day in Puerto Rico before our flight, we took a tour of the Bacardi Distillery. It is across the bay from Old San Juan in Cataño which is about a 15 minute Uber ride. There is also a ferry that only costs $0.50 each way, but Bacardi is still about two miles from the ferry terminal. We chose to Uber there, and to leave, we took a taxi from Bacardi to the ferry and then the ferry back to Old San Juan.

Complementary souvenir cups and drinks come with the tour.

Bacardi offers multiple tours, all which include a Bacardi beverage before or after your tour as well as a commemorative cup. We chose the “Historical Tour” which was the cheapest option at $15. They also had a tour plus rum tasting as well as a tour plus mixology class, both of which were around $60.

All in all the tour was fun, but if your vacation in Puerto Rico is short and you’re pressed for time, you won’t be missing too much by skipping this.

Other Food

In addition to more traditional Puerto Rican food, we also had pizza and tacos! For our first meal in Puerto Rico, we just stumbled into this cute little Mexican restaurant right in Viejo San Juan.

Tacos from La Guerita

We also decided to go to Pirilo which is a pizzeria (although they do have traditional Puerto Rican food for appetizers.) It is next to Punto de Vista Rooftop, and seemed to always be crowded and popular with the locals.


One of the reasons that makes travelling to Puerto Rico so fun is how easy it is. American citizens don’t need a passport to go, which means you can avoid the customs lines you would have to wait in to visit most other Caribbean islands. You also don’t have to bother with currency exchanges and exchange rates. I had good AT&T service in all the areas I visited without any international charges (although I cannot speak for other service carriers).

There are direct flights to San Juan from most major U.S. airports, and the airport in San Juan is only about a 15 minute drive to Viejo San Juan, where my Airbnb was located.

Viejo San Juan is only a small part of San Juan and has strict building laws due to the historical architecture there. Because of this, there aren’t many hotels located right in Viejo San Juan; most are located 2 to 5 miles away. I chose to stay in an Airbnb as there were many options in Viejo San Juan, and they were cheaper (we paid about $100 a night) than the hotels that were farther away. The Airbnb I chose was a block from the ocean and the historic wall surrounding Viejo San Juan.

A Note on Uber in Puerto Rico

Uber is available on all parts of the island except leaving the airport. You can Uber to the airport but you will have to take a taxi from the airport to your hotel or Airbnb, and they have standardized rates to each area. It was about $20 to Viejo San Juan.

Upcoming Trips

Thanks for reading my first ever blog post! I hope it will encourage you to visit and learn more about this often overlooked piece of America.

Stay tuned: for my next big trip I’ll be heading to Mexico to explore the Yucatán Peninsula with the Caffeinated Wanderer!

~ Kailyn

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This Post Has 2 Comments

  1. Chantelle

    First of all, Kailyn is your cousin? Mind blown, small world. Lol. Moving on … I love San Juan and seeing pictures of mofongo make me miss it more! I regret not getting out to el yunque as it was our original plan. I love reading about different experiences from places we’ve been to see how we can go again and have a explore in a different way

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