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Caribbean blogger

There are many dream jobs out there. Teacher, stock broker, business owner, boat captain, it all depends where your passions lie. What about Caribbean Blogger, would you add that title to the list?

Since 2009, I’ve been lucky enough to have the title, Caribbean Blogger, behind my name. I’m not here to boast or blow my own horn though, quite the opposite. I’m here to give you a look at the “REAL” life of a Caribbean Blogger. I want to give you a behind the scenes look at how this pirate was first inspired, stays inspired, and the pros and cons of what many consider a fantasy job. It’s not all rum punch sunsets and island hopping adventures, there’s a lot more to it.

I wanted to write this story to shine light on what myself and other bloggers/writers do. Why? Because I see a lot of comments on the RSR Facebook, Twitter and Instagram pages from people asking to be my assistant, saying I am lucky, or wishing they were me. While that’s nice to hear, there’s far more to it than just taking pretty photos and traveling to exotic island locations. Allow me this introspective brain dump and I’ll tell you the REAL life of a Caribbean blogger.

The Move

To learn the complete story of Mr. RumShopRyan, you have to start at the beginning. It started in 2001 with a move from Kansas to Naples, Florida. I had just graduated college from Pittsburg State University and didn’t want to move back to Kansas City like most people. I knew I wanted to live where people vacation.

I did the pros and cons on several states and finally decided that if I was going to go south, better go all the way. So I moved to Naples, Florida without a job and didn’t know a single person. Despite this, I was strangely absent of fear. It’s good to be young and dumb. But it ended up being one of the best decisions I’ve ever made.


I would get up every morning, run on the beach, then send out resumes. Three weeks later I got a job doing graphic design and launched into adulthood full steam ahead. All the while I was completely in awe of my new surroundings.

Towering palm trees, calm Gulf waters, and warm winter weather surrounded me. I was living in a tropical paradise where everything was new. I thought, how could there possibly be a place that could match the beauty of southwest Florida. Those are the thoughts of a naive Kansas boy that had yet laid eyes on the Caribbean.

The Trip

In 2007, a couple friends of mine decided to tie the knot and wanted a special destination wedding. Two years before that in 2005, Kenny Chesney put out his Be As You Are album which does an amazing job of capturing the laid-back island vibe. It’s a vibe that my friends and I lived every weekend. We would sip rum on the beach and skim across the waves in boats and jet skis and basically live the life Buffett and Chesney sang about. Be As You Are was the sound track to our salty lifestyle.

Because of the connection to that Chensey album, my friends chose St. John in the USVI as the location to exchange their vows. Attending that wedding was the beginning of my island addiction. Nothing would be the same after it.

St. John Trip RumShopRyan

We rented a villa on top of Jacob’s Ladder overlooking Turner Bay. Days were spent beach hopping in Jeeps and nights we bar hopped in Cruz Bay. They said their “I Do’s” on the soft sand of Hawksnest Bay. It was a magical moment, it was a magical week. It’s a week that I’ll remember forever and it ended up changing my life.

The trip only lasted a week, but somehow I felt at home. It’s as if the island wrapped its arms around me and gave me a warm Caribbean hug. It’s hard to explain, but I knew I had to find a way to visit St. John and explore all the island as much as humanly possible. That mindset ended up giving birth to an idea.

The Site

I’m not a rich man. How would I make my dream of exploring the Caribbean a reality? Though I didn’t have a lot of money, I did have a little creativity and a mountain of ambition.

Pittsburg State University gave me the graphic design skills that would help build a brand. A failed restaurant review company I started taught me how to build a website and write a somewhat coherent thought. Using those tools, I set out to create a website that would hopefully help me realize that Caribbean dream and inspire others to do the same thing. was born in 2009. It was a place where I could share the southwest Florida lifestyle with others that also seek a tropical escape. In the beginning I would share photos of Naples, Bonita Springs and Ft. Myers Beach. I would spend hours researching then writing about the Caribbean destinations that filled my thoughts.

I went in with the mindset that wasn’t just going to be a blog, it was going to be a business. It would be something I would work at nearly every day.

I learned that consistent content creation is the key to building an engaging audience. A large engaging audience is the key to attracting the attention of PR companies, advertisers, and business owners that want exposure. Grabbing the attention of PR companies and Caribbean businesses is the key to not only getting free Caribbean travel, but also getting paid to do it.

That’s the dream, getting paid to do what you love to do. Turning a passion into a business and inspiring others to follow their island dreams, that’s what is to me.

The Reality

That’s the dream, getting paid to do what you love to do. While this Caribbean blogger does get paid to go to some pretty amazing places and makes a little money from advertising, it’s not enough to live on. This is the reality from most bloggers, Caribbean or otherwise. While I do know a few who have managed to cross the magical threshold, quitting their job and writing full time, I am not there… Yet.

One of the most common questions I get is, “Is this your full time job?” No. During the day I work as an Inbound Marketing Agent for Impulse Creative, a marketing and website design agency here in Fort Myers, FL. Funny enough, I was hired because of my success with So you never know what doors can open from pursuing a passion.

Caribbean blogger

The reality of being a top Caribbean blogger is that it’s hard work. It’s coming home from work and then sitting back down at the computer to hammer out a story. I did this for the first 4 years, Monday thru Friday. It hurt my social life. It hurt my love life.

I had a past girlfriend tell me I spent too much time on the website. After awhile, she grew to resent the site and my island loving lifestyle. Finding the right partner that shares your same dreams and lifestyle is so important, that’s what I found when I met Castaway Crystal. The best part in finding a partner like this is that you have someone to share these experiences with. I’ve been to some pretty amazing places by myself. While solo travel is exciting, I’ve found that sharing it with someone who shares that passion is far better.

The Benefits

The benefits of being a Caribbean blogger are, in short, fantastic. They make all the hard work worth while.

After you have worked hard enough, long enough, and grown your audience to good size, the benefits will start to happen. What size of an audience do you need to start to garner the attention of the businesses and agencies that will want to send you to the islands? That’s hard to say, it’s different for everyone. All I can say is keep working and make connections with people.


Caribbean blogger

Travel is one of the biggest reasons I started It is the vehicle that allows me to visit the islands as much as possible, and do some pretty amazing things. I’ve judged rum competitions, sailed through the Tobago Cays in the Grenadines, pet nurse sharks in the Exumas, hiked to the top of a Caribbean volcano on St. Kitts, sipped a $1200 bottle of Cuban rum on Grand Cayman, danced the night away at a marina in Grenada and so many other experiences. I’m just a simple Kansas kid and it still blows my mind that I’m lucky enough to be able to do these things. And do them in the name of journalism.


Caribbean blogger

Born to Rhumb St John boat Charter

It’s always comes down to people–amazing, talented, generous people. Becoming a Caribbean blogger has allowed me to meet and proudly call some pretty amazing folks my friends. There’s rum writers, rum makers, sailers, musicians, bartenders, business owners, other bloggers, my readers and so many other people that has allowed me to cross paths with. The website wouldn’t be anything if it weren’t for all the Castaways reading the travel stories and drink recipes, for that I am truly thankful. For all the others, you know who you are, thank you. Getting to know you and traveling with you has been an amazing journey.


Caribbean blogger

After you have built up a website to a large enough size, a certain level of notoriety can happen. It can be a benefit if you like that sort of thing. I’ve been called famous before, but I think that’s far from reality. Internet famous maybe, which is an Everest step below being actually famous. Sure, I get noticed around southwest Florida, Key West and the USVI, where I spend most my time, but I wouldn’t necessarily call that fame. I relate it more to a guy who has his face on a quirky roadside billboard that people remember. Is that guy famous? Nah.

For me it’s weird. I have two sides of my personality that do battle when it comes to notoriety. On one side I do like the attention, it feels good to be noticed for all the hard work and to bring people island inspiration. Then on the other side, I’m really not that big of a people person. It’s an on-going internal battle between an extrovert that wants to be cool and an introvert that just wants to chill and quietly soak in the world.

The Drawbacks

While traveling the Caribbean for free is amazing, there are some drawbacks. There’s the long hours, frustration from lack of progress, strain on relationships, frustration from not know knowing how to build a website or design a logo, lack of marketing strategies, and poor writing. I’ve experienced all of these, but if you want something bad enough, you’ll knock down the walls of limitation and learn the skills it takes to make a successful travel blog work. It all comes down to how badly you want it.

The Public Eye

Sometimes people suck. If you choose to put yourself out there and share your life with people, there’s going to be people that feel the need to be negative. I believe that putting yourself out there is a great way to make your brand personable and relatable. People want to see that there’s a human behind a logo, this is especially important because we are talking about a blog.

When you do this though, you open yourself up to the haters. I’d say that 99.5% of all the comments and messages I get are positive. You Castaways are truly a great group of people. Then there’s that .5% where some thick skin is necessary. I’ve had people call me fat, bald, tell me I have bad teeth, sweat too much (hello, it’s the Caribbean!), am boring, am a shitty writer, and probably some other things that I can’t and don’t care to remember.

I laugh at these comments and move on. You can’t dwell on the negative, there’s rum drinks to pour and beaches to explore! But if you do choose to make a serious go of being a travel blogger, then you’re bound to run into this. It’s a drawback, but not one to pay much attention to.


Time, there’s never enough of it. As I mentioned earlier I have a day job. Island hopping is not my full-time occupation. After working 9-5, I get a quick workout in, have dinner with my beautiful girl, and then jump into the office for an average of two hours. It’s takes time to write a good story, edit photos, plan out a week’s worth of content, respond to comments, and try to grow the brand.

Another time drawback you might not think about is getting enough vacation time from your job. On average, most people get 3-5 weeks vacation from their job depending on time worked. That time vanishes pretty damn quick when you want to explore the islands. I’ve had to turn down numerous press trips in the past because my employers at them time wouldn’t give me the time off. I’ve even quit a job because one boss wouldn’t give me the time off so I could go to the Castaway Beach Bash I had put together on St. Thomas. F*** that guy!

I’m now lucky enough to have an employer (whom grew up sailing the Caribbean) that offers unlimited paid time off. A benefit that is nearly priceless for a pirate like me.

Stopping To Soak It In

It took me a while to realize that this is a drawback, but it is. I catch myself getting so excited to capture a place, that I forget to actually slow down and enjoy it. Often times I’ll be so busy taking hundreds of photos and shooting just the right video, that I miss the feeling of the place. I’m getting better at this though. Sometimes you just have to downshift into island time and go slow for a Caribbean minute.

The REAL Life

While I’m sure I’ll always see the comments that saying that I’m lucky or living THE LIFE, I want people to realize that the REAL LIFE of a Caribbean Blogger is more than just flowing rum and footprints in the sand. Don’t get me wrong, it’s an amazing ride for sure, one I wouldn’t trade for anything, but there’s also a lot of behind the scenes details that aren’t that glamours.

Caribbean blogger

If you have aspirations of traveling the Caribbean, or anywhere else in the world for that matter, I’m happy to help you build a blogging website that can make your wander lust come true. Just hit me up on the Contact Page or message me on the RumShopRyan Facebook page. I do blogger consulting and can help you develop a plan that fits your ambitions.


Caribbean Instagram

P.S. – Leaving soon? These recommended links below will help you save money and book your trip:

We use all the companies listed here or on the resource page. By booking through these links, the small commission we earn helps us bring you more Caribbean content so that you can save money and have a better island vacation. Crystal and I greatly appreciate any support!

About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.