Puerto Rico

San Cristobal

As the lights of San Juan showed up on the horizon I started getting excited to land. I hadn’t been to Puerto Rico in 4 years and then it was only for 5 days with the company I worked for. While I had seen some really great things in that trip, I was excited that I’d get 10 days on the island this time and only half of it was with work. Beyond that, I was really excited to see my girlfriend for the first time in almost a month.

As I got off the plane in early May, I was met with 80 degree temperatures, incredible humidity, and the sound of the tiny Coqui frogs singing in the night. The bus ride from the airport to the Caribe Hilton where we would be staying took about 10 minutes, which is about 10 less than if he had continued straight on to old San Juan. San Juan is a tiny island which is attached to the rest of Puerto Rico through short bridges and roads. Our first five days would be spent in the relatively newer, less historic part of San Juan where the Caribe Hilton is located along with some shopping and other large hotels.

Caribe Hilton
The view from our room at the Caribe Hilton

The Caribe Hilton is the disputed location of the creation of the famous drink, the Pina Colada. The drinks in the hotel were running between $15 and $20, so after meeting up with Sissy, we hung out with my coworkers while some of them enjoyed their outrageously priced drinks and we walked around on the hotel’s private beach. The tri-level pool and surrounding beach were great, plus there’s a grove of palm trees right by the water with hammocks hanging for guest use whenever they’d like.

Cueva ventana

One of the first things I was dying to do was to revisit an amazing cave I had seen 4 years prior, Cueva Ventana. I had been taken there by a local tour guide/cab driver previously and remembered the experience vividly. We had parked at a seemingly random gas station, headed up a dirt path, and hiked through some short caves with no other visitors in site, holding a flashlight from his glovebox. We traveled through a final pitch black cave before coming to the namesake of the cave, which is the “window” portion. The cave opens to the side of a mountain you are on, and drops hundreds of feet straight down. There’s a phenomenal view of a river running through a valley from here, while bats fly in and out of the cave above you.

Most of my coworkers were excited to join, so we asked for a van to drive us to and from at the cab stand of the hotel, which is where we learned what taking a cab in Puerto Rico would be like for the rest of the trip. The drive is an hour west of San Juan, in the town Arecibo. For 8 of us to and from the cave, plus the hour the drive would wait, we were given the “low rate” of $250. Soon after we would learn that no matter the length of the cab ride, by admission of multiple different cabbies, the charge would always be $20+. 10 minute ride from our hotel to old San Juan? $22. Airport to our hotel? $20. For all the great things we would see on the island, a cab meter wasn’t one of them.

Cueva Ventana
Cueva Ventana’s entrance

As we arrived at Cueva Ventana there were some obvious changes from the last visit I had made to this time. We parked in front of a sign reading, “Cueva Ventana Ticket Center”. Tickets were now required to enter, and each one cost $19. As we paid and headed uphill we were met by workers handing us hardhats. We were led by a tour guide past the cave entrance I remembered using the trip prior, to a different entrance. The tour was pretty well run, however other tourists were moving in and out of the cave as we were handed flashlights and guided in.

Cueva Ventana Entrance
This is the entrance we used the first time I went

The caves were as beautiful as I had remembered, and the end of the path leading to the window was still great. The view is something that needs to be seen in person. We were instructed not to go to the edge of the cliff as the earth could potentially break away causing us to fall down the cliff. I had fond memories of standing on the edge and looking out on the island, so as others had done as the guide headed back to the start of the cave, of course I headed to the edge to survey my new surroundings. Heading back to the hotel I reflected on the past hour or so. The cave was as beautiful and awesome as I had remembered, but I also lamented over the commercialization of its beauty. It somehow seemed less special now, maybe due to the large groups moving through it, the hardhats being worn while walking upright through the cave, or the loss of the adventure it had held previously. I’d still tell anyone who asked that they should visit, but only with the expectation being what it has now become.

Cueva Ventana
Sissy and I at the window the cave is named for
Cueva Ventana Edge
The opening is larger than it looks!

Icacos island

After a day of required work activities, we followed it up with a sailing tour on a catamaran out to Icacos Island. I’m not a big boat guy, in fact later in this post you’ll really see what I mean, however this boat ride was a really great time. We shuttled to Fajardo, which is about 45 minutes from San Juan, and arrived at a busy marina. As we got under way and the sails went up, we cruised at a surprisingly fast pace toward some islands on the horizon. After 45 minutes of sailing we stopped at Icacos Island and got to put the water slide attached to the back of the boat to use. After jumping off the top of the boat for a bit and shooting down the water slide, we snorkeled a bit to see what we could find. There were few fish in this area, so not a lot to see, but we were having fun just swimming and jumping anyway. The boat pushed off and headed a short way from the island, where we were told the snorkeling was better. Here we saw small groups of small fish, nothing overly exciting, but still a good time. The sun decided to come out for our trip back from the islands to the marina, which lead to a very warm and relaxed nap for most of us on top of the boat. The entire trip probably took 4-5 hours, and though not very adventurous, it was nice and relaxing.

Bio bay

That night we would head to one of my favorite parts of Puerto Rico, the Bioluminescent Bay. We set out from San Juan around 6:15pm in a shuttle that the kayaking company, Kayak Puerto Rico, sent for the reasonable charge of $30 per person. Funnily enough, we shuttled back to the marina in Fajardo we had been at just hours before. When we were ready to set out around 8pm it was pitch black and in the high 70s outside. We put on our life vests and waded through the warm Caribbean water to get into our kayaks. After paddling through the bay, we reached the mouth of the river that we’d be kayaking through in the dark to reach our destination.

Fajardo biobay
I’d love to put pictures of the bioluminescence up, but it can’t easily be captured by cameras

In my opinion, the journey to the bio bay is phenomenal. When else will you kayak through a narrow river, typically 10-15 feet wide, in the dark, surrounded by mangrove trees and all kinds of wildlife on all sides? Sissy and I were lucky enough to get to the front of the line and get into the river before anyone else, which is the only way to go. Behind us we heard people crashing into mangroves and struggling to paddle in unison as the kayaks are two seaters. We got to paddle easily and blissfully down the river, pretending, at least in my mind, to be in a scene from Pirates of the Caribbean.

After a 20 minute journey through the river, going around bends in the dark and having a great time, we saw the mouth of the lagoon open up in front of us. As we paddled, I told Sissy to look down as she stroked through the water. The paddle lit up a fluorescent blue as it pulled us through the water. As we journeyed in further, the bioluminescence grew stronger, at times looking like a scene from the movie Avatar. After a quick rundown on bioluminescent plankton and what produces the blue color, we set off to explore on our own. Sissy and I headed pretty far out in the lagoon, which is rather large. We would come across areas where fish were lighting up brilliant blue in the water, and areas where the glow would fade. After about 20 minutes we were almost out of sight of the rest of the group, when a kayaker came and found us. He turned out to be a guide and told us we were missing the rest of the group leaving.

We unfortunately had to head back out of the lagoon much sooner than we would have liked, we were having such a great time we may have never left given the option. Now we were stuck at the back of a 15 kayak long line, and it seemed that about half of that number may have never kayaked before. We were stuck in the back of a line that at times would literally move backwards, as the ocean flows into the lagoon, meaning we were paddling against the current now. After passing some fellow tour members who had crashed into mangrove trees, we finally got back to the marina and hopped out, reflecting on one of the most amazing natural sights we had seen.

El yunque rainforest

The next day we would taxi with a tour guide (you’ll find most taxi drivers double as tour guides) to El Yunque rainforest, which is the only tropical rainforest in the USA. This was my second time there and I don’t think a guide is necessary, but this time I’m glad we had the guide we did. He mentioned that Mina Falls, the popular waterfall you can swim at the bottom of, would be very crowded that day. He brought up a waterfall with a pool to swim in that his friend had journeyed into the jungle and found. He didn’t know of anyone but his friend having been to it, and wasn’t 100% sure on where it was, but had a good idea. We eagerly jumped at the opportunity, and soon we were parked on the side of the road near a bridge and heading off to find this place.

El Yunque
Our guide taking us down toward the waterfall

As we journeyed we soon found that there was no path, and every way we turned there were spider webs at eye level with large arachnids staring at us, sometimes within inches of our faces before we noticed. Our guide began carrying a stick to knock down the webs before we ended up covered in them instead and we traveled on. After about 30 minutes we came upon a beautiful waterfall sloping about 25 feet down into a crystal clear pool at the bottom. Our guide headed around the pool, which had a rock wall coming up out of it that he was walking on when he tripped on a vine and fell, sliding a bit and coming within a foot of falling off of it. His leg was cut, pants were ripped, and he was bleeding a little, but luckily that was the worst of it for him. He was lamenting more about how he didn’t bring his swim trunks to test the pool, so I jumped in and tested it out for him.

El Yunque Waterfall
The pool we found after hiking for 45 minutes

To my surprise, the pool must have been 20 feet deep or more and felt amazing. The water was perfectly clear and not too cold. Sissy and I swam around for a bit, enjoying the beautiful surroundings, before we dried off and started the trip back. Going back we made great time and got to the van within about 20 minutes since we knew which way to go now. As she and I got in to leave, our guide was busy showing pictures and video of the place we had found to some small groups of tourists passing by. It sounds like that pool will eventually be his new tour, once he brings his machete to cut a path. Unfortunately that place may never again be the way it was this time, but it was great to experience it while it was still relatively untouched.

old san juan

The next day we would switch from the Caribe Hilton to the Posada San Francisco hostel as my coworkers left for home. The Posada San Francisco is directly on the Plaza Colon, within a hundred yards of Castillo San Cristobal, one of the two fortresses in San Juan. The hostel is on floors 4-8 of an old colonial building with an elevator from the early 1900s bringing you up and down. At $50 a night for a private room for two, it was the least expensive accommodation that we found with decent reviews. The hostel has a very religious tone, with a cross hanging over every bed, and what appears to be Mary holding baby Jesus on every key card.

We walked around the city most of the day, checking out San Cristobal, Calle Hospital, the pink house of cats, and eating lots of delicious local food. Pork mofongo was one of my favorite local dishes, which is mashed plantain, garlic, and some sauce, along with meat usually. The rum capital of the world has some great mojitos and pina coladas and if you find the happy hours, two for one deals aren’t uncommon. We learned that old San Juan is a cat lover’s paradise as there are more stray cats here than anywhere I’ve been. Luckily the residents of the city enjoy their feral cats and put food out on the street for them and care for them to a degree. There are plenty of sickly cats wandering around, but most seem to be in pretty good shape with the possible case of fleas being their biggest threat. Hospital street is a great pedestrian only street leading toward the pink house of cats which is lined with strays lazing about. The house is south of El Morro fortress and is there to care for stray cats. You’ll know which one it is by the dozens of cats outside of it and the great view of the ocean from the city wall in front of it.

Old San Juan
Sissy petting one of her new friends on Calle Hospital
Old San Juan Cats
Cats in front of the pink house of cats
San Cristobal
Looking out from San Cristobal toward El Morro in old San Juan

scuba diving

The following day we had booked a SCUBA trip from Fajardo with a local shop, Seaventures Puerto Rico. We were shuttled there by the company, which will drive you to and from Fajardo for $30 per person from San Juan. The shop offers dives for certified divers and for first timers as well, which cost $120 for 2 tanks if you’re certified, or $150 for a short first dive and then a full second if you aren’t certified. We headed out for a long ride to Palominito Island, the same island where Jack Sparrow left Angelica a pistol and one bullet in Pirates of the Caribbean 4. With the island in the background, we headed out on our first dive. The ride there was really choppy to say the least, with waves smashing into us the entire way. Most of the divers had a tough ride getting to the dive site, with sea sickness occurring left and right. Once we got in the ocean things calmed down and we were lucky enough to see turtles, giant lobster, all kinds of fish, and even spotted eagle rays. The dive sites were well chosen and worth the discomfort of the sea sickness I experienced. Sissy had no problems with sea sickness, but she was one of the only people that can say that!

Seaventures Puerto Rico
Our second tank dive with Seaventures
Spotted Eagle Ray
One of the spotted eagle rays we swam with


The next day Sissy convinced me to make a great choice in renting a car. It was a choice I was very reluctant to make as I don’t have a great sense of direction and prefer cabs, but the cab fare was outrageous on the island and we planned to venture a decent ways away. We took a taxi back to the airport to rent a car from Alamo. It was $23 a day for an almost brand new Toyota Yaris, which was cheaper per day than the 15 minute cab ride to the airport to pick it up. There are tolls on the major roads on the island, which the cab drivers will moan about and charge you extra for, however they’re under $2 each time you hit one and there are only 2 major ones we ran into on the 120 miles or so we covered in either direction from San Juan.

We decided to head to some local beaches for the day, ideally away from other tourists. We took a 45 minute drive from the airport to a great beach called Mar Chiquita which is west of San Juan before Arecibo. We hardly saw any other tourists there, two that I recall out of a large crowd of locals. The beach is beautiful, there is a volcanic rock wall that formed along the ocean. The ocean pushed its way through the rock over the years (centuries? Millennia?) and formed a large, sandy pool, protected from the ocean’s waves by the volcanic rock wall. It’s a truly unique beach that doesn’t seem to have been discovered by many tourists yet. The swimming is great, the sand is nice and fine, and the best food we had on the entire trip, and coincidentally the cheapest as well, was in a food stall here. There are palm trees, coconuts, and plenty of spikey volcanic rock to make you feel like you’re on another planet.

Mar Chiquita
The picture doesn’t do it justice, Mar Chiquita is definitely worth a visit

After spending hours at the beach we decided to move on to La Poza del Obispo, a bit west of Mar Chiquita and just outside of Arecibo. This beach is another locals beach with no other tourists that we saw. There are no real facilities here to speak of, no bathroom or food around, just a nice pool of water connected to the Caribbean with an amazing show being put on every few minutes. As you look toward the ocean, there’s a volcanic rock wall to the left, and when a big wave comes in it slams into the wall, shooting water up 40 feet in the air. It’s a great time swimming in the pool and having ocean water rain down on you as it slams into the rock. After watching the show for a while and swimming around a bit, we took the hour drive back to our parking lot in old San Juan near the harbor.

culebra island

For our final day on the island we drove the 45 minutes back to Fajardo to the ferry terminal and bought tickets to ferry to Culebra, an island about an hour from Puerto Rico. We got in line around 8am in order to buy tickets for the 9am ferry for $4.50 round trip per person. I took some Dramamine so I could ensure I didn’t have a sea sickness repeat from our SCUBA trip. When we boarded I found the boat to be nicer than I had expected for the price paid. It probably fits 200 people or so, was clean, and relatively modern. After getting up so early to get to the ferry terminal, I slept like a baby until we arrived at Culebra.

The major attraction in Culebra is Flamenco Beach. It’s consistently rated one of the top beaches in the world, and we’d find out later that day why. We decided to try to beat the crowds to a smaller, less crowded beach that is known for its snorkeling. We took a taxi for $5 each to Tamarindo beach, which is a thin strip of rocky sand that overlooks a bay that opens to the ocean to the left. Swimming out toward the opening and looking into water revealed sea turtles under and around us, eating sea grass and swimming about. There might have been 10 other people at the beach at 11am, but the cab driver told us he’d drop 20 people off or more in the next half hour, so we enjoyed our time with the turtles while we could. We probably saw 8 turtles or so in the small area we explored. There are said to be rays in the area as well, although we didn’t end up seeing them that morning. After a bit we saw a large group of large tourists wrapped in ill-fitting life vests wading into the water 100 yards away, so we swam back to the beach and called a cab to take us to the famous Flamenco Beach.

Tamarindo Beach
One of the many turtles we saw at Tamarindo Beach

The 10 minute cab ride was another $5 each and we got dropped off in a busy parking lot with food stands and lots of tourists. We were there on a Monday in May, I can only imagine the crowds on a Saturday or Sunday in summer! We grabbed some food at one of the open stalls, avoiding the shark fin option as we both disagree with mass execution of sharks for their fins. After finishing up we walked toward the beach, which is hidden from view by palms trees and bushes. Getting our first glimpse of the beach as we neared the end of the short path, we immediately understood the reason it’s talked so highly of. The sand is the nearest to a white sand I’ve seen, and I’ve never felt finer anywhere. The water has two distinct colors, for the first 100 yards from the beach it’s a vibrant turquoise, after that there’s a sharp line where it changes to darker, ocean blue. Palm trees line the beach, giving shelter from the bright sun, and leaving coconuts lying around.

Flamenco Beach
Sissy and I on Flamenco Beach

Immediately after finding a nice coconut tree to set our towels under, we regretted not staying on Culebra for a night or two. Flamenco is about as perfect as a beach gets, and after 5pm when the ferry leaves back to Puerto Rico I’d imagine it’s even more magical. The only negative things to be said about the beach are that the tourists don’t seem to clean up their trash very well, which leads to small pieces of trash on the beach that Sissy and I couldn’t help but spend some time picking up, and the area used to be a military site which you can see by the abandoned tanks at the far end of the beach. Even with those two flaws, I couldn’t imagine a place I’d rather lay and let all my worries dissipate than there. We spent hours walking around the beach, swimming, and napping, before reluctantly heading back to the ferry.

Flamenco Beach
The more crowded side of Flamenco Beach

That night would be spent saying goodbye to old San Juan, packing up, and caring for Sissy’s toenail, which ended up coming off after she stubbed it the night prior. The amount of pain she went through losing her big toenail, and me running around old San Juan finding bandages and disinfectant still couldn’t put a damper on the amazing day we spend on Culebra. The next day we would return the rental car, drink a bottle of wine on the curb in front of the airport, and fly to Chicago, where we’d part ways for the next month and a half until our big journey began in Iceland!

top things to to

– Rent a car

– Spend more than a day on Culebra

– Stay in old San Juan if you’ll stay in San Juan at all

– Order rum drinks if you’re drinking

– Check out the caves

– Definitely SCUBA if you can, snorkeling is pretty great in the right places too


Make sure to check out our adventures in Iceland!

Our video of Puerto Rico



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