For the record, I hate the word yolo. However I couldn’t resist the pun and the fun (see, I can’t help myself) it represents in relation to my recent birthday trip.

2016 has been the “year of the bucket list” yall. So when I booked my very first ever solo trip six days before my birthday I was definitely embracing this popular and annoying term.

Spontaneous, yet intentional. Yep, that about sums up the sentiment behind my decision to escape these New York city streets for some party of one fun (sorry I’m on a roll) in San Juan, Puerto Rico.

Which was huge considering the ginormous party I had 365 days ago…

My party last year was a 200+ RSVP extravaganza that people are still talking about today. It was a semi-spontaneous turn up with my birthday twin George 2.0 at a restaurant literally around the corner from my apartment.

A year later, that restaurant is closed.

However my ideas on how to celebrate my life have opened.


I was feeling significantly better about celebrating another birthday without my mother this year. Even still, had you told me on July 1st that I would be celebrating alone I would’ve laughed (or maybe even cried) in your face.

I mean, I “DO” alone. I am an only child after all. However the twist is that I am an extroverted only child, so lonely is not a exactly a word that I would use to describe my childhood.

Slumber parties and being able to bring friends on family vacations was the norm.

Another norm, was the fact that having a summer birthday as a kid sucks.

All my friends were either always away at camp or on a family vacation on or around July 15th.

However as an adult having a summer birthday doesn’t suck.

In fact it is buck (sorry I couldn’t resist).

No but seriously, it is the ultimate turn up. Travel plans still come into play, but for the most part people are glad to show up and show out on a summer night in order to celebrate your life. See exhibit A: My birthday last year.

So while I could’ve easily had another “birthday dinner” or “meet me here for drinks” party, the idea of this “typical” celebration wasn’t appealing to me this year.

That and half of my friends, like during my childhood, were out of town the weekend of my birthday. See, sometimes still sucks.

But, unlike four year old Robbie, almost 34 year old Robbie was cool with it.

Turns out the older you get, the simpler life becomes and in my case, the more you enjoy your own company.

Side bar, moving forward, I will now refer to myself as an extrovert with introverted tendencies.


Anyways, as a self acclaimed extro-intro-vert, all I really wanted for my birthday this year was to be by the beach.

I am a Cancer, so water is my jam.

Water and spontaneity…

Which is precisely how my yolo solo birthday trip came about…

I was sitting at a bar, solo, after brunch with friends (who had also just announced that they would be out of town during my birthday weekend). Again, cool with this. I have a good book in my purse and had essentially been alone all weekend.

See the day before I spent the entire day cleaning my apartment, watching Netflix and drinking Rosé. Alone. It was the best day ever.

So when I contemplated my birthday plans for the following weekend I thought…

Hey I can do just this and be just fine.


But then as I was sweeping and body rolling down my 20 foot long hallway I heard a voice say…

Celebrate however you want. But be sure to celebrate.

I half listened, half ignored this for approximately 24 hours…

Which brings me back to Sunday. Post brunch. Two friends just confirmed their birthday weekend absence. Brining the RSVP No total to “almost all my closest friends.” Good book in purse. Doing just fine.

But before I could open my book I started chatting with two ladies sitting next to me. It was a typical single black woman bar conversation. What natural hair products do you use, coupled with how are you handling dating in the city only to lead to my favorite inevitable part of: Aye!!!! Look at us and our #BlackGirlMagic! Let’s do a shot! Yolo!

However somewhere in between girl, “I love Carol’s Daughter” and “I hate dating in New York,” I mention my birthday was coming up that Friday.

They asked me what my plans were and I recited, verbatim, what my spirit had told me in my hallway the day before…

I am going to celebrate. Just not sure how. Water will definitely be involved.


“Go on a trip!,” one of my bar sistahs says.

I’m looking at her like, did she not hear me say my birthday is in six days…

“I know a lot of sites that have great deals to the Caribbean. You can probably get a good deal to Puerto Rico for less than you think,” she continues.

Then she went on and on about what hotels were the best, what restaurants to try etc. while I took notes so fast on my iPhone that I am surprised I didn’t crack the screen.

It was all so exciting. However deep down inside I knew it was going to be too expensive and I would just make a mental note to do something similar to this next year.

But still I went home and looked online. And to my surprise, she was right, the deals were great (great considering I haven’t been on a real vacation in years, so I have actually have no clue what great is).

I saw one of the hotels she mentioned, 5 stars behind it’s name and I clicked “buy” all in less than 10 seconds.

10 seconds after that, I was body rolling down my (clean) 20 foot hallway, off to try on swimming suits.

It has the best and I was so excited running around the city the next couple days preparing for my trip.


The lead up was all a magical blur. One day I’m dancing around my apartment in New York city only to find myself pumping out the same silly dance moves in my hotel room in Puerto Rico four days later.

And the moment I inhaled that salt water air, every single misconception and fear I had about traveling alone disappeared…

I wasn’t afraid.

In fact I felt free.

I wasn’t lonely.

In fact I was surrounded by the best love there is. Self love.

And I wasn’t alone.

In fact I met some of the most incredible humans ever…

There was Jeff from Chicago who was down to stay up until midnight at the bar just so he could tell me happy birthday. He too was about that yolo life since we both knew he had to be at the airport by 4:30 a.m. Good thing we both like Macallan single malt scotch whiskey. A commonality amongst many. My second favorite shared interest being our childhood love for Squirt soda.  So random, so wonderful. I can hear his laugh right now as I write this…

Then there was Joe from New Jersey. He’s the real MVP. His passion for education was infectious. I almost messed around and applied to be a high school teacher when I got home. I spent hours on my birthday with him and he was the third person in less than 24 hours that told me I was brave for traveling alone for my birthday weekend. Third person to say it, but the first time I heard it. His heart was just pure like that.

He was so great that I was tempted to spend the whole day and evening with him after he offered to meet me for my birthday dinner.

But I knew I had to do this part of my trip solo. It was going to be the greatest challenge and I wanted to face it. To see how it felt, to see if the loneliness I expected traveling alone to provide would join me at dinner…

It didn’t.

I had the MOST AMAZING MEAL EVER! I drank red sangria so strong that it would lay most people out under the bar and I had the best service on the planet.


The entire experience was truly magical. No tears, no sadness.

Okay, there was one time that I almost did cry.

The bartender was so inspired by my solo yolo trip that I almost turned on the waterworks when she told me I was brave in Spanish.

Eres Valiente.

Our entire conversation that evening was a beautiful Spanglish melody. And while the lyrics were difficult to follow the tune of her sentiment was not.

Cue the tears now…

As I was getting up to leave the bar, she says, “Espera espera (wait, wait)!” And then, better than the fireworks show on my fourth birthday at Disney, was a show that I will never forget.

All the servers and my bartender hermana surrounded me, clapping their hands and singing the birthday song just how the Cali girl in me likes it…with rolled “R’s.”

The waterworks are close…

I feel a body roll coming on…

However the real tears came when I tasted how marvelous the cake was.

Note, Cancers are not only spontaneous water lovers, they love food so much that it can easily bring them to tears. Me at this moment = case in point.

On my way back to my hotel my poor Uber driver probably thought I was crying because I was alone on my birthday, and was sad because of it.

When the truth was I was alone on my birthday, and I was glad because of it.


I could go on and on yall, but I need to go plan my next yolo solo trip.

Sike. Who am I kidding? Spontaneous women, even at 34, don’t plan anything!

Because Lord knows, I certainly didn’t plan for this trip to be one of the best gifts I could’ve imagined.

Now excuse me while I go and put a big fat check next to Travel Alone on my bucket list!

Where are all my travelers at?! I need suggestions on where I should go next. Leave them below.


2 Responses

  1. So very happy you enjoyed your time in PR. It always brings me such peace and joy whenever I am there – I was there for my birthday also, the day before. Perhaps try driving through our beautiful country…it has so much to offer! I particularly enjoyed the west – Oregon, Washington, Vancouver (BC, Canada), Montana and Minnesota. Good luck with your future trips and plans! If you need additional information, don’t hesitate to reach out. We could always meet up for drinks in Harlem. Take care.

    • Hi Melissa!

      Thanks for this. I am totally a beach girl, and can’t believe we were in PR almost at the same time!?

      I also love a good road trip, so I’ll be adding these suggestions to the list for sure. xoxo

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