How to Drop Your 9 to 5 and Move to Puerto Rico

by / ⠀Startup Advice / March 21, 2022
laying on the beach with a laptop

Where else can you find an island with hundreds of miles of breathtaking coastline, monumental castles, a  mountaintop tropical rainforest and a nightlife that envies that of Las Vegas without the need for a passport or work visa?  “La Isla del Encanto” offers not only exquisite scenery in the form of both environmental and human beauty, food that you are guaranteed to think about for the rest of your adventurous life and a lasting impression that there is truly a place to live your dream.  Often forgotten that as a territory of the US, Puerto Rico is available for open travel without hassle, so you can do just that.


“But I don’t know Spanish…”

Nonsense.  The tourist communities within the bustling capital city of Puerto Rico are full of people that have transplanted from the United States; mostly from the Northeast or Florida.  Puerto Rican students are taught English and many grow up in bi-lingual households.  You’ll pick up the words and phrases you need to know in no time.  Are your bags packed yet?  You’ve got a plane to catch.

A Room with a View

Hands down, the best bet for an ultimate experience is to live in Isla Verde.  This hub of activity can offer you quality apartments, many with ocean views, in a prime location for an affordable price.  Get a friend to share the adventure with you and it’ll only cost you $350/mo for a fully furnished apt if you shop right, and aren’t too worried about living like a king or queen.  Internet is comparably priced, and an obvious must if your internet business is what’s going to keep you afloat.  Not to worry if that’s not your gig – plenty of jobs are available in the service and hospitality industry to keep you from going broke; you can even join the hundreds of entrepreneurs that have started their own service-based or novelty business on the island after being tired of stressful lives in the states, everything from beach glass jewelry to car detailing.  Head east to Fajardo for the chance to work on fishing or diving boats if you have the affinity for it; the ones who do live a unique and appealing lifestyle.  There’s no reason to get a car, almost everything you need is within walking distance or a 50 cent bus ride away.  If transportation is truly something you can’t live without, save an extra $600 before you drop your day job and pick up a scooter when you get down there.  Besides, being on a Vespa could mean the difference between a 5 minute vs 5 hour traffic jam when the cruise ships hit the port.

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Live it Up!

Recreation, relaxation, night life.  Puerto Rico has it all, and lots of it.  Want an exquisite evening on top of the world?  Enter the rooftop uber-lounge, complete with pool, known as the Water Club and instantly be surrounded with the sweet night air, a view of the ocean and a clientèle composed of everything from swanky-clothed bachelorette-partying statesters to local fashionistas and celebrities.  Trips here must be timed right and used sparingly to keep from breaking the bank, but it is sure to impress and offer the opportunity for quality connections.  Try Al Alhambra a block away for some pre-game action, classic jukebox tunes and uniquely rude-yet-irresistable service from the locals’ favorite bartender,  “Hawaya.” Need a regular, inexpensive pre-gamer available at the local Supermercado?  “Medalla” is the local beer, only available in Puerto Rico and rates similar to your favorite domestic national brand; don’t worry, you’ll learn to love it.  Looking for a true club experience?  Brava in the El San Juan hotel is the premier destination.  Pounding reggaeton, techno-twisted laser lights and plenty of eye-candy.  TIP: Be sure you are making friends everywhere.  The local restaurant burger-grillers double as security or bartenders here.  No cover and dollar drinks are nothing to shake a stick at, just make sure you treat them well. Make sure to get comfortable with historic Old San Juan, which offers both daytime pleasantries and a nightlife for every taste; every day can be a whole new experience with dozens of bars/clubs, cigar and novelty shops, and a history that provides a very unique backdrop for it all.

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Postcard-Perfect Surroundings

This is what makes it all worth it.  The local beach is a fantastic daily destination, one end often offers swells that provide a wicked day of riding.  Need a surfing lesson, so you can catch waves and turn some heads?  Instructors await you beachside.  Countless coastal destinations each provide a unique experience.  Luquillo beach is remarkable and the local food offered in nearby kiosks will have your mouth watering.  Need a little extra adventure?  Of course you do.  Several outlying islands are a short drive and a $5 ferry ride away.  Camp on the picturesque Flamenco beach in Culebra.  Snorkel endlessly for some of the most gorgeous fish you’ve ever seen, practice your shrimp or lobster catching, and try to spot the rare conch.  Make sure that you experience El Noche Del San Juan, one of the biggest beachside gatherings you’ll ever see, complete with the climax of thousands of people flopping into the ocean backwards at the stroke of midnight.  TIP: Ocean Park in Condado is the destination for the young and affluent crowd, you won’t be disappointed.

Need a truly once-in-a-lifetime experience?  Make an overnight stop on the island of Vieques with an evening trip planned to Mosquito Bay.  Guided tours are available via kayak or pontoon boat to this magical wonder.  Within this body of water reside millions of organisms that glow bright green as a method of self-defense.  Instantly, as you enter the water and disturb their peace, you are surrounded by a magnificent bright green aura.  Few have ever been able to catch this on camera, so soak in the unforgettable experience; no one will ever fully understand the experience you have had.

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The key to integrating yourself in this culture is to embrace it as your own.  Networking skills here can provide you with a lifetime worth of experiences and stories to tell for the ages.  The locals love their island, they party like nobody’s business until 10am, and are more than proud to show the hidden wonders of the area to you.  Take them up on their inevitable offers to explore something new, step outside your comfort zone and make the best of it, you won’t soon forget.

Bought that plane ticket yet?

Contributor Drew Peneton has lived and worked in Puerto Rico and is now working on his current project transitioning soldiers into civilian life at

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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