4 Days in San Juan, Puerto Rico

Puerto Rico was always one of my dream destinations in the United States (Others in the list include Hawaii & Alaska). I was enamored by what I had seen in music videos and documentaries. So when we had a week off during the holidays in December, we booked our trip to Puerto Rico. While the flight tickets from the continental US could get really expensive during winters, we traveled on Christmas eve to save some money and returned before the New Year’s eve. We were a group of 6 people and booked an AirBnB in San Juan which fit our budget.

While Puerto Rico is a territory of the United States, it’s a very unique island with it’s own culture and heritage. San Juan is the capital and largest city of Puerto Rico. The flag of Puerto Rico represents and symbolizes the island of Puerto Rico and its people. 

Accommodation Tip: Drawing from their personal experience, few of our friends advised us to book the AirBnB in a safe location based on reviews (even better if you can score accommodation from AirBnB certified Super-Hosts!). Some neighborhoods are shady and better left alone.

Day 1 – Aventura Cueva Ventana

Our group flew from Boston to San Juan on Christmas Eve in a Jet Blue flight and checked into the AirBnB late at night. We picked up our car rental from the airport for the entire duration of the trip ( booked in advance). After a good night’s sleep, everyone was excited to explore San Juan. We began the day with a quick breakfast at a local cafe nearby. The neighborhood where we stayed (Calle Benitez Castaño) is no-frill and authentic. Right outside our apartment, we spotted a wild and splendid graffiti wall, Since it was Christmas day, most of the restaurants and excursions were closed for the day. However, I had researched in advance and got confirmation from Aventura Cueva Ventana through email that they were open. It was an hour drive from our accommodation in San Juan.

One of the most beautiful caves in the world, Cueva Ventana sits atop a limestone cliff in Arecibo, Puerto Rico. We were taken on a short guided group hike up to a window overlooking a beautiful valley. The view was dreamy, unlike anything I had ever seen before. Cueva Ventana itself means ‘Window Cave‘. Make sure that you are wearing comfortable and grippy shoes as it could get slippery specifically close to the cave which is the main highlight and final destination of the hike. We were also given helmets to protect ourselves just in case. The hike was easy in my opinion and totally worth it. The caves close at 4:30 PM and it’s highly recommended to reach in time to make the most of the hike and spend quality time at the top. There were also some local vendors on the way out selling artisan jewelry and other souvenirs.

By the time we got back, we had built up quite an appetite and started looking up restaurants that could possibly be open on the Christmas day. We hit the jackpot with Playa Brava Beach bar. Patio dining with gorgeous views of the ocean and delicious cocktails & food. The weather was perfect that day. After our meal, we walked out to the deck, soaked some more of the ocean views and headed back to our AirBnB in San Juan.

Day 2 – Old San Juan

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500 years of history, beautiful colonial architecture and tropical colors make Old San Juan one of the most enchanting destinations in the Caribbean. This UNESCO world heritage site is best explored on foot. Everything from the cobblestone streets to the houses, restaurants to the monuments are a colorful blend of Puerto Rican culture and lifestyle. Bright colored Spanish colonial buildings with distinct balconies and doors can be found throughout the neighborhood of Old San Juan.

Our first stop was the Castillo San Felipe Del Morro, a 16th century Spanish fort with jaw dropping ocean views. Located at the entrance to the San Juan harbor, the fort also known as El Morro played a significant role during the Spanish American war. You can get in for a small entry fee and go up to the top of the fort. Check out the Garitas, small enclosures where the Spaniards stood guard during the war. They offer gorgeous views and are a perfect place for your insta worthy shots.You will get a lovely view of Santa María Magdalena de Pazzis Cemetery, one of the most beautiful cemeteries in the world. The cemetery can be accessed through a tunnel and is the burial site of some of the most prominent people in Puerto Rican history. Gaze at the Atlantic Ocean and catch a glimpse of La Perla, the neighborhood where Luis Fonsi filmed his music video for “Despacito.” La Perla was formerly home to slaves and homeless servants who were not allowed to live within the city walls. The expansive gardens around the fort are impressive as well.

Walk for 15 minutes and you’ll reach San Juan Gate also known as Puerta de San Juan. It was the main entry into the walled city during its Spanish colonial era. We walked out the gate from the city and were greeted by blue waters of the bay. There is an inscription on the gate ‘Benedictus qui venit in nomine Domini’ . It means ‘Blessed is He that cometh in the name of the Lord’. Everything we laid our eyes on was beautiful. Old San Juan is unlike any town I have ever been to. It’s unique, vibrant and seems to have preserved it’s legacy over the years.

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Walk inward towards the city for 5 minutes and you will come across the San Juan Bautista Cathedral. This oldest church in United States was visited by sailors and travelers entering San Juan thanking God for a safe journey through the ocean. It has been rebuilt over the years after being hit hard by multiple hurricanes. The church is located on a street called Calle del Cristo which is one of the most beautiful streets in Old San Juan. Afterwards, we strolled the town for a while spotting graffiti, buying souvenirs and just loving the vibe altogether.

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After a quick bite and a cup of coffee, we left for Fortaleza Street also known as the ‘Umbrella Street‘. It is a sight to behold. It had started raining slightly. The narrow street with cobblestones and pastel colored buildings has colorful umbrellas floating above (See the featured image of this post on top). There are one of a kind boutiques and stores around the street. Use the free trolley if you are not in the mood to walk uphill or downhill while exploring the town. There are 2-4 routes on any given day. It could also help you save time if it’s a short trip and you only have a day in Old San Juan.

Day 3 – Isla Verde Beach & Bioluminescent Bay Tour

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Day 3 was all about relaxation, at least during the day! For the night we had booked a Bioluminescent Bay tour which included 1.5 hours of kayaking under the starry sky.

I picked up breakfast from the neighborhood cafe third day in a row. Being an early riser and someone who needs food within 30 minutes of getting up, I had made it a routine to go grab a nice hot cup of coffee and pick breakfast for the group. As we had planned to spend an entire day at the beach, we were in no rush.

Isla Verde beach is located at the glitzy resort strip 15 minutes away from Old San Juan. While the surrounding area is busy, the beach was very laid back and quiet. One of the best urban beaches on the island, it is a long beach with wide expanse of soft golden sand.

At a walking distance from our beach was the Alambique Beach Lounge. We had a scrumptious meal there and picked up a bottle of homemade Cocito from the bar. CoCito is an alcoholic mixed drink, containing Coconut rum, Coconut Milk, Condensed Milk, Cream of coconut, Eggnog, Cinnamon and Nutmeg. It’s the most delicious cocktail ever! We kept going back to the bar the entire afternoon to refill our bottle with Cocito.

After enjoying the beach for a few hours, we went back home to freshen up, grab a meal and drive to Fajarda for our Bio Bay Tour with Pure Adventure.

Bioluminescence is a phenomenon that causes the water to glow bright blue with every splash and movement. It is caused by single-celled microorganisms called dinoflagellates which light up and cause this magical effect. There are only 5 bioluminescent bays in the world which can be visited to witness this enchanting phenomenon. You are only allowed to swim in a few of them. There is an online calendar available to see how clear and bright it will be based on the cycle of the moon.

Our tour started at 8 PM. We were 2 people each on a Kayak and our group followed our guide through a narrow dark river. The only light we had was from the sky (stars and moon). We did not carry any phones with us for safety. Finally we reached a lagoon and all the kayaks huddled together to experience the bioluminescence. While we had read that all pictures available online are edited and the real experience is not as mesmerizing, we didn’t anticipate it to be so disappointing. The effect, if any, was minimal and nothing like what we see in pictures online. Again, we could be unlucky as there are other environmental factors affecting the intensity of the phenomenon but it was nothing like we had anticipated. However, the experience of kayaking under the starry night was very exciting. The guides were knowledgeable and helpful.

Casa Bacardi Tour & La Placita de Santurce

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Puerto Rico is home to Bacardi’s largest rum factory in the world. With capacity to produce 100,000 bottles every day, it is a haven for rum lovers. With 3 different options available, we had booked a guided tour in advance. The story of Bacardi family is legendary and it was a nice touch with all the personal mementos and artifacts from all those years. Get to know how Don Facundo Bacardí Massó immigrated to Cuba, revolutionized rum-making and then set up home in Puerto Rico! The process of making rum and the respective equipment is very cool and getting to experience it was truly rewarding. The tour ended with a cocktail and souvenir to take back home.

After heading back to our apartment and resting for a few hours, it was time to party during our last night in Puerto Rico! La Placita de Santurce is the ultimate party place in San Juan. Lively and fun, the street was full of people out in the open drinking, singing and dancing! I had heard a lot about the Puerto Rican party spirit but to be a part of it for real was out of this world. We partied hard, hopping from one bar to another until we were sloshed for good. We couldn’t have imagined a better last night on this Island or a more perfect ending to our lively trip!.