San Juan, Puerto Rico

When my friends asked me where I wanted to have my bachelor party, I wasn’t sure where I wanted to go.   I had some criteria: late February, in a warm place with a beach, nightlife, and a good restaurant scene.  I didn’t want people to have to worry about passport issues. Puerto Rico was the first place that came to my mind.

Old San Juan puerto rico

Old San Juan

At first I was a little skeptical about PR as a destination, with reports of high crime and the limited Google results for the phrase “San Juan bachelor party,” but I did some more reading and became convinced it’d be a good place.

Why was I planning my own bachelor party, you might ask? I know that’s something for the best man and wedding party to do, but I was not ready to cede control on something travel-related. Yes, I’m stubborn that way I guess.

Old San Juan

Castillo San Felipe del Morro puerto rico

Castillo San Felipe del Morro

I wanted to have a full morning to see Old San Juan, a UNESCO World Heritage site, so I arrived a day earlier with my future brother-in-law, Will. We stayed at the beautiful La Terraza, an old Spanish-style boutique hotel in the heart of historic district. With high ceilings, ornate wall paintings in the restaurant and front desk area, and dark wood doors and paneling, the hotel was replete with Old World charm. You’d think these features would ring up a sky-high price tag, but I paid $150 including San Juan’s exorbitant hotel tax, which was a song compared to our hotel costs at the Marriott the next two nights in Condado. Upon check-in the English speaking front desk girl offered me a beer while she went over the map of the neighborhood and gave me recommendations for restaurants and sightseeing. The room was awesome, with really comfortable beds, a modern bathroom, and Netflix installed on the TV. Will arrived too late for our Marmalade reservation, so we settled on a pizza tavern-type place called Pirilo, which turned out to be great.

Old San Juan cobblestone puerto rico

Old San Juan looking north

Old San Juan is a treat for the sightseer interested in history and architecture, and urban design. It’s narrow, cobble-stoned streets, lined with pastel colored buildings and plazas, are remnants from its days as an important seat of the Spanish empire.  The district has undergone revitalization in the last few years; most buildings seemed had a fresh coat of paint, and the streets were clean. Flowers adorned the balconies, adding splashes of color to an already colorful scene.

Plaza de Armas san juan PR puerto rico

Plaza de Armas

Old San Juan by Casa Blanca

Old San Juan by Casa Blanca

Old San Juan is really compact; it’s about a 15 minute walk east-west and a 10 minute walk north-south. There are six or seven east-west running streets and about eight that run north south in a neat grid. So it was almost impossible to get lost here.

San Juan cats puerto rico

San Juan was full of cats

On the western end of Old San Juan is the Plaza de Armas, an excellent example of a Spanish-style town square bounded by colorful administrative buildings. I bought a coffee at a little stand called Cuatro Estaciones Cafe that seemed to be in the main draw of the plaza. After satisfying my caffeine fix, I made my way over to Cafe Mandolin, a no-frills Puerto Rican diner, where I took the opportunity of ordering something you don’t see everyday in the US—scrambled eggs and chicken. As expected, the coffee was excellent—I didn’t have a weak cup of coffee the entire four days.

Castillo San Felipe del Morro

Castillo San Felipe del Morro

Castillo San Felipe del Morro

View from Castillo San Felipe del Morro

Castillo San Felipe del Morro san juan puerto rico fort

Castillo San Felipe del Morro

Castillo de San Cristobal san juan puerto rico

Castillo de San Cristobal

I walked along the western edge of Old San Juan, following the fortifications with the bay to my left. The old Spanish fort of Castillo San Felipe del Morro juts out into the Atlantic Ocean to the city’s west. Full of ramparts, casemates, cannons, and moats, the fort was taken over by US during the Spanish-American War in 1898. $5 gets you access to Morrdo and another fort called Castillo de San Cristobal, on the eastern edge of the main part of Old San Juan.

Old San Juan wall

Old San Juan wall

As I was adjusting my camera settings outside an old building called the Casa Blanca, I backed up into in the biggest pile of dog s___ in history. It’s funny because I didn’t see a lot of dog s___ around on the streets of Old San Juan; I just happened to slowly smush into the only one in Old San Juan. I spent the next 15 minutes on a mission to cleanse myself of this canine curse. A fountain near the Puerto de San Juan gave me a source of fresh water for my shoe bath.

I met Will back at the hotel. Before meeting our friends at our hotel in Condado, we ate lunch at Café St. Germain, an almost Parisian café restaurant known for its sandwiches and salads as much as for its ambiance. The upstairs rooftop bar is apparently the place to go at night.

Children's musem san juan

Children’s musem


We took a cab to the Marriott and hung out in the late afternoon as everyone trickled in from their different flights. It really meant a lot to me that my friends would travel from as far as California to be with me at my bachelor party 4 time zones away. It was also cool to have my friends from my different stages of life—childhood in NJ, the Army, grad school, and DC—finally meet each other.

We met in the lobby and headed to the Cigar House in Old San Juan to hang out before dinner. Cigar House is the ultimate hang out place for guys. It’s in an old building, fronted by a cigar shop with all sorts of paraphernalia like lighters and cigar boxes. In the back there’s a lounge area with big couches and tables and old-time decorations. Even further in the back there’s a bar with a huge selection of Caribbean rums, including my favorite—Ron del Barrilito 3 Star. We hung out on the couches and each tried the obligatory cigar. I accidentally inhaled my first puff, coughing as I laughed.

We had the kickoff dinner at Aguaviva, a Latin seafood place that reminded me a lot of a place you’d see at Miami Beach, with neon lights, an open kitchen, and waiters dressed in white. We loved the food, including the oysters, but everyone went nuts for the fried chicken dish, which is weird because the restaurant is known for its seafood. The fried chicken had a darker color than what we’re used to on the mainland. I have to look up the recipe.

At the recommendation of a waiter, we headed to a bar called La Factoria. As the name suggests, the bar occupies a former factory. The bar has three big rooms. The first room you enter is a regular bar; the second, through a door a little behind the bar, is a small seating area for eating; the third, a big bar area with a stage with a DJ playing a mix of Latin and pop music. The décor was–I can’t put my finger on it–shabby chic? Tile floors, string lights hanging above, walls with faded paint. The rooms were of intentionally run-down but in a cool way. It reminded me of the “ruin pubs” I saw in Budapest (see my blog post on Hungary). We asked the bartenders to cook us up rum-based cocktails, which were all amazing on both the sour and sweet end of the spectrum. I only regret not taking note of the drink names so I could try to recreate at home.

El Yunque National Forest

The next morning, after a substantial breakfast at Orozcos, a few blocks down from the Marriot Stellaris, we met our tour guide, Raul, for a short day trip up to El Yunque National Forest, the only tropical rainforest in United States Forest System. 7 of the 12 guys at my bachelor party (including me) went on the day trip. Originally I had 12 people going, but I think I scared a few of the guys by including the word “hiking” in my email describing what the day’s events were. I think hiking was the last thing on some people’s minds after a long night of drinking and gambling all night at the hotel casino. That was fine; I didn’t want to drag anyone along on the trip if they didn’t want to be there. Plus, we’d be back at 330pm so we’d still have a lot of time to hang out.

The seven of who went had an awesome time. The trip didn’t really involve hiking at all; in fact, the only hiking we did was go up a steep but short hillside to a cool waterfall and natural pool. The ride to El Yunque gave us the chance to chat with each other and ask Raul questions about Puerto Rico. Raul drove us to several points of interest in the rainforest, including the visitors center, an overlook tower where we could see all the way to the Atlantic Ocean, and two waterfalls.

El Yunque puerto rico

El Yunque waterfall

The highlight was another set of waterfalls—the one with the steep climb—in the middle of the rainforest where we swam in the crystal clear rainforest water pool at the base of a long waterfall.

El Yunque puerto rico

Raul laying making a hat out of a leaf

El Yunque puerto rico

Climbing up the second waterfall

El Yunque puerto rico

Juan Diego’s double waterfall (first one)

Puerto Rico rainforest waterfall

Me taking a dip in Juan Diego’s double waterfall (2nd one)

For lunch, Raul took us to La Muralla, located right in the park on one of the main access roads. It looks like a ramshackle roadside restaurant from the outside but the food turned out to be one of the best meals I had in Puerto Rico. I had the fried chicken, rice and beans, and beef plantain pocket. We enjoyed dining inside the covered patio seating area, next to a huge boulder that makes up one wall of the restaurant.

puerto rican cuisine Muralla

My brothers at La Muralla

El Yunque restaurant La Muralla

El Yunque restaurant (La Muralla)

puerto rican cuisine food

Fried chicken, rice and beans, beef plantain pocket

After lunch Raul took us to an area outside the park where there is a natural rock-water slide. I think his company, Natural Wonders PR, has a special relationship with the landowner; he paid a guy at the house we stopped at, and we made our way down the hill to the river. We had tons of fun sliding down the wet rocks on our butts and into a cool pool at the base of the slide. My friend Jon had his Go-Pro camera, which got us some great videos of ourselves going down the slide. It was a lot of fun. Raul’s only instructions were to lean forward in a seated position, keeping your arms to your side to guide you, and to keep your feet together. Raul said that when he was “50 lbs lighter,” he used to be able to “surf” down the slide in a standing position.

natural waterslide puerto rico

Me halfway through

natural waterslide puerto rico

The guys taking a dip after the slide

natural waterslide puerto rico

My brother looking huge

Natural Wonders PR was great. They worked with me to tailor my itinerary to fit a bachelor party’s needs (i.e. not starting the day at 8am); and offered a good price that included both the water slide tour and the waterfall tours—a combination that’s not included in their normal set of itineraries. Raul didn’t get antsy when my friends showed to the lobby 15 minutes late, and he even provided a cooler full of beers, cokes, and rum. One of my friends went down the waterslide with a beer in hand.

Dinner that night was at Yerba Buena, a Cuban restaurant right near the hotel. I figured it’d be easier to go to a restaurant that we could all walk to rather than have to take cabs to the fancier Santaella that I had a made a reservation at. Yerba Buena was beyond awesome—Will couldn’t stop raving about how great it was. The service was superb, they gave us welcome shots, the food was excellent, the drinks selection was great, and the prices were fair. For many of us it was our first taste of mofongo, the distinctly Puerto Rican dish consisting of fried plantains, yucca, and other ingredients. A lot of us got the dish called Chuletas “Can Can,” a pork dish with a lot of delicious fat and meat on it, topped with crispy pork skin. Probably not the healthiest dish but it was really good.

La Placita

We spent the rest of the evening exploring La Placita, an area with a cluster of bars and restaurants in the Santurce district. I wish I had time to see this area during the day, as the architecture was pretty cool. Next to a beautiful market building called Plaza del Mercado was Asero Cubano Kitchen and Bar, where we hung out for a while enjoying the cocktails and the lively scene. Again the décor inside was shabby-chic and the place had a hipster vibe to it. House music played at low enough volume and we could actually talk to each other.

We ended up back at the hotel at the casino to wrap up the night. Some of us won back the money lost earlier in the weekend, so no one went home broke. The next morning we chilled at the beach until our flight times creeped upon us, becking us to rejoin civilization at home. I felt a tinge of sadness.

All in all, this was an awesome bachelor party and a perfect send off by my friends and brothers into marriagedom. It was also a reminder that I have some really great friends who I would be able to count on in a pinch.

 Travel Map


Kevin is based in Washington, DC and writes about his travel adventures in the Mid-Atlantic region and around the world. Through entertaining writing and eye-catching photography, he aims to provide readers with useful information as they plan their next trips.

  • Donald

    So great. I have someplace a picture of Emily and Carolyn at the same waterfall


  • Joanne Craw

    I truly enjoyed reading this blog entry! You describe PR and other places so well that I want to visit or revisit as in this case. I loved it there also and think I was at that same town square! I’m so happy that you had a great time and that your brothers and friends were there to celebrate your bachelor days with you! Lots of love and happiness wishes to you! XO mom
    PS Suggestion! maybe you could do an Oakland NJ post on your next visit up!!!!

    Sent from my iPhone


  • Gia Newman

    I’m so glad I stumbled upon this blog before my trip to PR, we just got back from a week trip. I visited El Yunque and we had dinner at La Factoria twice. I really think Puerto Rico is underrated as a travel destination, it has so much more to offer than just beaches and resorts. The culture, history and natural wonders gave us such a rich experience. Next time you go I recommend the Caves of Camuy and the bio-luminescent bay in Fajardo (be sure to book the bay tour early, we also did the electric boat option instead of the kayak and I think we enjoyed it more than the people in kayaks). Thanks for sharing!

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