Where to Go and What to Do in Puerto Rico if You're Hot, Sexy, Single or... None of the Above

I initially went to Puerto Rico to clear my mind, relax, get sh*t-faced drunk, and party. Little did I know that I would be doing some soul-searching and discover a thing or two about myself in life and love.

Before heading to Puerto Rico, I did little to no research on what I would do once I arrived. I had seen that commercial they air on TV and I thought, 'it's an island - whatever it is, I'll find it. I'll just walk along the beach until I get there.' It would be an adventure. Well, let me tell you now that Puerto Rico is much larger than say, Alcatraz Island. "What?!?" you say, "But I've never seen a Puerto Rican in my life, besides in New York and those baseball players and that one guy Manny Pacquiao beat up." It's true. Puerto Rico is huge and there is much to do. Walking along the beach all the way around would've probably taken me a year. In fact, it would take about a day to drive around the main island along the coast.

I did have an AMAZING time on my one week stay, but looking back, there are a few things I would've done differently.

Let me get some important particulars out of the way first:

Population: About 4 million
Language: Spanish, but most people speak English as well
Currency: U.S. Dollar (USD)
Economy: $17K+ Median Household (About half of Mississippi, the poorest in the U.S.)
Average Temperature: 82 Degrees
Passport: Not needed if you're a U.S. citizen
Hotness of Women: 5 Miss Universes in their history - making them one of the most successful participants ever
Gambling: Legal
Closing Time of Bars/Clubs: Varies on day of the week, area, but generally 2am, unless located in a hotel, then 5am+


So I began my trip with 5 nights in San Juan, Puerto Rico, and left my last 2 nights open to adventure or "wingin' it". I knew when booking my hotel that I wanted to stay someplace ON the beach. While there were many hotels in Puerto Rico, it was important for me to find one where I could walk straight from my hotel room in board shorts right into the ocean. I booked at La Concha Renaissance, by far the hippest, most modern hotel around San Juan. If you're young, hot, and single, this is the place for you. That's not to say there are no families or couples, because there are, and they far outnumber the single, but this place had a great combination. When you think of this hotel's style, think The W, or The Standard. (See pics below)

Other hotels I would recommend on the water would be the El San Juan Hotel and Casino, which has a great nightclub located inside. It's a Waldorf Astoria hotel, so it's classy and classic in feel. The ambiance is nice, but the lighting and vaulted ceilings would make it intimidating for some to hit on women.

You could also try the Ritz-Carlton, but let's face it. That hotel is for old, rich people who go to bed at 10pm and drink Apple Martinis. If you want to brush your teeth with a bottle of Jack - La Concha is probably a better fit.

These are amongst the nicest hotels in the area and are priced accordingly. Either bunk with a few roommates to reduce cost or go to Hotels.com for some better deals.


Admittedly, most people will tell you that Sunday, Monday, and Tuesday night are relatively dead in Puerto Rico. This is true, because Lord knows I tried going everywhere I could. Typically, by rule-of-thumb (or common sense), ask the hottest people in your hotel where to go each night. Also, this gives you an "in" and the possibility she might want to come with you.

A great place to go for happy hour any day of the week or after-hours (Sun - Tues) is a place called The Brickhaus in Old San Juan. The owner's name is J.P., who hooked me up with a few of his rum drink specialties - and they're darn good. You'll find a mixture of locals just getting off of work and tourists. Afterall, it is right behind a Senor Frog's.

On Wednesday and Thursday, you'll want to go to an area called La Placita, which is essentially a row of bars that fill up a block. Most of the people spill out into the streets and most of the bars are open-air. There's not much dancing that goes on here (think Pacific Beach), but a few places have dancing towards the back. The drinks here were the cheapest that I found around San Juan (about $5), whereas at the hotel I was paying about $10.

On Friday and Saturday, you should get dressed up. Start out with drinks at La Concha, where a mix of beautiful locals congregate, then head over to Club Brava (above), located inside El San Juan Hotel. Afterwards, if you're still not satisfied or want something more dress-casual, check out a place called Taiguey Beach Club. This place was full of locals and mixed in a DJ with karaoke (my fave!). Here's a word to the wise, never try to intermix Bon Jovi when the locals are having fun dancing salsa. Who knew that 'Livin on a Prayer' would kill the party? Not to mention, who knew that Bon Jovi could hit ridiculously high notes? I couldn't. That guy deserves an award. I literally had two fans singing along as everyone else watched the 'gringo' kill the party. (Well, f*ck you! Cause I'm never going back there again anyhow! LIIIIVIN ON A PRAYERRR!!!)


What kind of bachelor blog would this be if I didn't give you some tips to success? Not that I had any, I mostly ended up with my face laying on the toilet seat and yelling out towards the banging door: "uno momento!" But this is what I saw from other people when I was nervously peeking out from behind the speakers:

- Learn just a bit of the language - no matter what country you're in. It's more endearing then someone just assuming they know your language. If you're not going to make an effort, why should she? Hola, Como Estas?, Hablas Ingles?, Como Te Llamas?, De Donde Eres?, Me gusta hacer el sex contigo. See? That's not so hard to learn.

- Take some salsa lessons or just watch some free videos on YouTube. Practice it, because the folks in Puerto Rico like salsa. It's a beautiful, sexy dance. If you're not comfortable with it, stick with the mega clubs and tourist joints.

- Put in the time. I found this country to be one of the least slutty countries I have ever been to. Whereas in the states, or Argentina, or Brazil, you'll routinely see people making out on the dance floor. Not so much in Puerto Rico. You're better off sticking with a tourist if you want to go home with someone that night. If you have time, ask the girl out for dinner the next day, etc. THEN try and shove your tongue down her throat.

- Do not sing 'Livin' on a Prayer'.

In closing, while Puerto Rico has had a disproportionate amount of Miss Universes, particularly in comparison to their population, I found the women to be VERY hit or miss. Like Brazil, there is a great mixture of dark and light skinned women, but unlike Brazil, there was just no consistency in looks. One thing that should make all men happy is that the majority was largely female at almost EVERY place I went. I also felt very unintimidated by the guys, who I didn't find to be that good looking, nor that aggressive - which is very rare for a latin American country (or in this case, Commonwealth).


Not all beaches are created equal. (Read my Best Single's Beaches in the World.) When I laid eyes on Flamenco Beach (or sometimes called Flamingo Beach) on the island of Culebra, I fell in love.

No where else on the big island of Puerto Rico can you find such clear, calm waters. One of my favorite things to do on beaches is to lay right on the sand where the water can gently lap over your body. The water was too rough around San Juan. Check out the map below. The islands of Culebra and Vieques are to the right.

If I had to do it all over again, I would have spent 3 days on the island of Culebra, 1 day on the island of Vieques (a cool little beach town feel with a lot of gringos), and 3 nights in San Juan.

Go to Sun Bay on Vieques, but as soon as the taxi drops you off, walk all the way to your left side of the beach to set up camp. The water is clearest and most peaceful in that area.


Like Costa Rica, one of the best parts of my trips was something unplanned. In CR, I had rented a car with a stranger - spur of the moment - and we drove 5 hours through the countryside to the zip line tours in the rain forest and stopped in little towns along the way. This time around in Puerto Rico, I specifically left two nights where I had made no arrangements for accommodations. I figured I would rent a car and see where that took me.

Well, in talking to people, it was apparent that I needed to make my way to Vieques and Culebra in search of the best beaches. So after a night of Saturday partying and 30 minutes of sleep, I packed up a toothbrush, board shorts, and an extra t-shirt, and took off to the Ferry about an hour away. In Vieques, I met some cool guys from Texas who I chilled the afternoon away with on Sun Bay. Later that day, I made my way to an area of the island called Esperanza and walked up the street stopping at each place, inquiring about available rooms.

About 6 stops later, I was hot, sunburnt, and starting to worry. Then... I stopped. I grabbed a Gatorade from the fridge and began talking to the gal at the front desk for about an hour. We just talked about life and the choices you make. I told her I wasn't worried about finding a place tonight, something would happen. She leant me her cell phone and I began calling almost every place in town. No luck. Last place: Casa De Tortuga. It just so happened they were right up the street and they had an opening for one night.

If you go to Vieques, I highly recommend you stay at Casa De Tortuga. It's like staying at your buddy's place, only a lot nicer and cleaner. The guy who owned the place, Matt, from Colorado, was about as accomodating as they come. In the morning, we "winged-it" and he found me a charter flight to Culebra. There was a gas shortage on the island, so Matt ended up driving me to the airport himself.

Once in Culebra, I knew I had to make my way to Flamenco Beach and there was only one place to stay on that beach. If that didn't work out, I had to stay on the other side of the island. Rather than walk and take that chance, I rented the last vehicle they had - a golf cart. My first stop was Flamenco Beach. And it lived up to its hype. I needed there to be an opening at the villas on this rather secluded beach. Please. I drove up the gravel road feeling like there would be no chance. I was livin on a prayer. And. That. Prayer. Was. ANSWERED!!!! One villa left, so I checked in, threw my stuff down and made my way to the beach.

I needed an umbrella to protect my sunburnt body and I scoured the beach for the right spot for the guy to plant the umbrella. He asks me if I'm by myself. I say yes. He says I have the perfect spot for you. And he places me right behind 6 single women from Minneapolis. They literally turn out to be some of the coolest, non-pretentious girls I have ever met. We talked the rest of the afternoon until they had to catch the ferry, but I have a feeling we'll be keeping in touch.

Later, after a nap, I was ready to see if there was any nightlife to be found on this tiny island. It is a Monday night. I get into my golf cart and make my way down the forested gravel road. There are no doors or windows on my golf cart and it goes about 15 mph on the bumpy road. It is pitch black and about half a mile to the main road. All I could think about was Texas Chainsaw Massacre and what I would do if my golf cart broke down. Book it for the road, or head back to the villa? What if it broke down right in the middle? I tell myself not to look behind me. I do. It is pitch black, but I keep thinking that someone is going to be sitting in that back seat staring at me.

Finally, after wetting my pants several times (thanks goodness for board shorts!), I make it into the tiny downtown area. I end up hanging out with a couple from Portland and a couple from Louisiana. They're both camping out on the campgrounds on Flamenco Beach. I offer them a drunken ride home, because there are pretty much no other cars on the road and I'm told it's okay to drink and drive, so I put my drink in the cupholder and we hit the road. Once we get to the campground, one of the guys says he's got a half bottle of the best rum in Puerto Rico. Heck, it could've been the worst bottle and I would've been in.

We all sit around in the darkness, toes in the sand, waves lapping in the background under the brightest, most amazing number of stars you've ever seen. As I ask the married couple how they knew, I couldn't help but think about how great it would be to enjoy this with my own loved one. They went on to tell me that they were relatively well-off, used to the finer things, and roughing it by camping on the beach for a few days. It wasn't easy, but they were doing it together and challenging each other with their love.

You may think I love bachelorhood - and this blog does nothing to refute that - but I love the idea of love more than anything else. It's just that I won't settle.

It breaks my heart not to be able to share these moments with the woman I'll grow old with. As much as I love a night out, drinking, dancing, and partying - there was no better moment for me on this trip than sitting on that beach at 3am, vulnerable, open, honest, and real.

Seeing genuine love is beautiful. It hurts, but lets me know I'm alive.

Thank you, Puerto Rico.

Kevin L.
The Silicon Valley Bachelor

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  1. these girls on the beach don't look to bad.. ;)

  2. Yeah, they're okay. Haha, they're beautiful!


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