Living in Jamaica; Our Nomadic-AF Adventure Begins

Living in Jamaica; Our Nomadic-AF Adventure Begins

Living in Jamaica was our first travel adventure together and it all started because we were unhappy with life in the States. We barely saw each other, we worked non-stop, and we had no quality of life.

We had both traveled independently but never as a couple… at least not long-term. The way things were going though, we decided that we’d had enough. It was time to quit our jobs, sell everything we owned (which was almost nil) and leave the country as quickly as possible. This was January 2011.

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We Found Cheap Flights to Montego Bay, Jamaica

There is a little game that those of us living in the Upper-Midwest like to play during the winter months. It’s called, “Let’s get the fuck out of Dodge“. The goal of the game is to scour the internet daily to find cheap flights to somewhere, anywhere, warm. We played this game together religiously.

Nomad Tip
If you can be flexible on your location and time frame you can find some really great deals to some really cool places.

Websites like give you the flexibility to search by month and by region which allows you to find the best deals available on flights.

living in negril kiwi screenshot
Choosing a flexible location and date will get you the cheapest tickets.

And then one evening we hit the jackpot; $99 one-way from NYC to Jamaica! Nevermind that we were hundreds of miles from NYC. We’d figure that out later. We pondered uprooting our lives and moving to Jamaica for roughly five minutes before Natasha said, “Fuck it. Let’s do it.

Getting our Affairs in Order and Getting the F out of Dodge

living in negril virtual hitchhiking

The cheap flights we found were only good for one day, three weeks out. Plenty of time. We gave notice to our jobs, sold off what little owned, said goodbye to our friends, and that was it. The adventure was beginning.

We still had one little problem; we were roughly 500 miles from our departing airport. Enter, Craigslist’s rideshare. If you haven’t heard of the concept, which many haven’t, rideshare is exactly that. You post when/where you’re leaving from and your end journey promising to chip in for gas/snacks/tolls/etc. Think virtual hitchhiking.

Well, it just so happened that our rideshare was a guy named Jason who happened to be a real-life freakin’ rocket scientist. So, for 10-12+ hours we chatted with this dude who was beyond brainy on our way to New York to start what would be the first leg of a life-changing trip for both of us.

24 Exhausting Hours in NYC

Here’s something I am probably going to mention more than once on our blog; if you want to live a nomadic lifestyle, it pays to be flexible.

We found super-cheap flights as well as cheap transportation from Ohio to NYC. The only problem was, we were arriving in NYC 24 hours before our flight departed. Time to get flexible.

We already knew the amount of money we had available for this adventure of ours was pretty low. Just one night’s lodging in NYC could pay for weeks worth of beach-time in Jamaica. So, we cheaped that shit out.

We spent the next 12 hours checking out all of the cheap\free tourist attractions we could find in the city. The following 8 hours were spent playing games and sleeping on the floor at JFK Airport. Glamorous, I know.

living in negril - sleeping in JFK
Cheaper than a hotel and no bed bugs.

Finally, four hours before our flight, we were allowed to check in at the gate and pass through security. Nope. Another freakin’ hitch. The not-so-friendly gate attendant (probably because it was 4:30 am) decided that since we didn’t have proof of onward travel we couldn’t board the plane.

Oh, come on! After speaking with several managers, we were able to convince them that we’d take the risk in Jamaica if we were refused entry for not having proof of onward travel.

Nomad Tip
Like most nomads we only travel on one-way flights. The problem is if you’re flying internationally the country you fly into will want “proof of onward travel”; a bus or plane ticket that proves you will leave the country before your visa expires.

There are a number of websites where you can “rent” a plane ticket for proof of onward travel to avoid the situation we just found ourselves in.

If we get deported before touching foot on the ground, that’s all on us! Good news folks, we breezed through airport security in Jamaica. But the entire plane ride we were a nervous wreck for sure! From then on, we always have proof of exit when heading to a new country.

Getting from Montego Bay to Negril, Jamaica

Finally, after nearly 40 straight hours of traveling, we were in Jamaica. We were still 2-3 hours from Negril though. From our research, we knew that the 3-4 hour trip from Montego Bay to Negril was going to cost about the equivalent of one week’s rent in our apartment.

We were on a super-tight budget and there was no way in the world we were paying that. We spent 20 minutes asking around and finally found a friendly shuttle driver with two empty seats on his bus. We quietly slip him $20 and we’re off.

Well, horror of horrors, it turns out we’re on a shuttle to the Hedonism Resort…and Swinger’s Week has just started. Fuck! Every freakin’ one of those creepy-ass old couples asked us if we were excited about the upcoming festivities. Gross! Since the average age on the bus was around 60, 25-year-old Natasha was getting a lot of attention. Blah!

Trying to keep to ourselves we took in the gorgeous views, treacherous roads, and more than one moto accident. We were already smitten. It was warm, colorful, and just the escape we needed. We were in heaven.

After dropping off the swingers at their resort, our driver decided his job was done. He booted us to a taxi run by his friend for the remainder of the journey. A little shady but whatever, we saved around $80. Do you have any idea how much rum you can buy in Jamaica with $80? A whole fucking lot of it, trust me.


Our taxi got incredibly lost trying to find our ‘hotel accommodations’. And for good reason. We knew the general area where it was supposed to be located (past the 7-mile beach, past the roundabout, and towards the cliffs) but didn’t realize it would be hidden behind a giant hardware store down a dirt path that was lined with wild goats.

cheapest possible living in Negril
Cheapest possible living in Negril, Jamaica.

As the taxi pulled up, we started to get an idea of what we’d gotten ourselves into with the world’s cheapest rent available in Negril. The first person we met was Rasta John…an old white dude that was constantly high, drunk or both. Usually both. He was harmless though and turned out to be a really nice guy.

First impressions are everything though, and this guy did not disappoint. He ran up to our taxi and, no joke, fell down shit-faced drunk (it’s before noon btw). He stumbled and caught himself a total of three more times before getting us to the ‘reception area’ (which was just the owner’s house).

There we met the owner. Another very interesting fellow, and another old white dude. Apparently, there was a problem with our ‘reservation’ (Rasta John forgot to tell the owner we were coming) and we had to wait a while on the porch (alongside several feral and flea-ridden dogs) while they cleaned our room. 

Finally, after a LONG couple of days of travel, we were moved to our room for some much-needed R&R. We were hot, sweaty, and exhausted but also enlivened. Our room consisted of a single bed, one window, and about two feet of walking space. Everything else including the bathroom and kitchen was shared with several locals who worked/ran the hostel for free rent.

Cooking and living in Negril
Cooking and living in Negril

We spent almost two months living in our little shack. We were steps from the beach and a short taxi ride to the cliffs. We made a lot of really good friends living there and were quickly adopted by the locals we lived on the “compound” with.

Nomad Tip
Speaking of taxi rides in Negril, check out our blog on how to get around Negril on the cheap using route taxis. They’re so much cheaper than private taxis or shuttles.

In retrospect, out of nearly 8 years of traveling now, that may have been the best couple of months we’ve ever had in our travels.

The St. Anthony Soup Kitchen in Negril, Jamaica

An expat we met one day mentioned that she volunteered at a local soup kitchen. Paul and I were intrigued. This was about a month into our adventure and, believe it or not, getting shit-faced drunk on the beach every day can get kind of boring.

We met with the boss of the soup kitchen, Ms. Pearl, and offered our services. Working the soup kitchen was an incredible experience for both of us but especially for Paul. He got to work alongside numerous Jamaican women cooking some of the most authentic Jamaican food we’ve ever eaten.

I mean, these women were tough as nails, generous AF, and oh-so-inspiring. Ms. Pearl had her own restaurant and still volunteered 3 days a week to feed the homeless. She also took care of little ones before and after school and did so much more for her community in her free time.

living in Negril - St. Anthony Soup Kitchen.jpg
St. Anthony’s Soup Kitchen

The soup kitchen served nearly 200 starving Jamaicans 3 times a week. We saw some really sad sights but it definitely opened our eyes. “Workin’ gals” would drop their babies off to be watched while they went to make some money and homeless men would save soup bones in their pockets so they could gnaw on them until the next time the kitchen was open. It was 100% an eye-opening experience that was both depressing and inspiring.

While Paul and the gang cooked, I helped with the front of the house handing out tickets and organizing the line to get people fed as fast as possible. Seeing children with almost nothing so happy and healthy gave me a whole new perspective on life. Yes, they don’t have shoes… but they make the most of what they do have. They appreciate EVERYTHING. They embrace school, learning, and family. They are rich in their own way.

The soup kitchen was generous to us too. When Paul got deathly ill with parasites due to drinking contaminated water, the church helped take him to the hospital and get his meds. When we left, the girls in the kitchen loaded us down with a variety of local spices to get us through our impending trip back to the states. We have never met a kinder bunch of folks throughout our travels.

If you feel so inclined any donation, big or small, would really help the soup kitchen out.

Paradise in Orange Hill, High Above Negril, Jamaica

While working at the soup kitchen during the first month, we met a gal we’ll call Julie. She was a small white girl who seemed A-okay. We were kinda sick of shuffling back and forth each night in our single bed and she just so happened to have a cabin for rent up in the mountains above Negril in an area called Orange Hill.

Living in Negril Orange Hill
Paul checking out the new yard in Orange Hill.

We went to take a look and WOW what views. Our little cabin was perched on the edge of a cliff over-looking the Caribean Ocean. We took her up on her offer and gave her $200 for the first month’s rent. Well, paradise quickly changed.

We were at least a 30-minute uphill walk, through ganja fields, to anything… including the nearest taxi stand. This made getting food and drinking water near impossible without a car. Julie had promised that she went to town at least 5 times a week, so figured we could catch a ride with her whenever. That’s until she ghosted on us.

living in negril - our shack in orange hill
Our little shack in Orange Hill.

About a week after we moved in our little gringa went on a 5-day heroin binge!!! She had locked herself in the house and only sporadically made attempts to drive into town (once turning back after five minutes because she “wasn’t feeling well”). Uh, oh.

living in negril - sunset from the shack
Sunset from our little shack in Orange Hill.

Cinnamon Bread with Velveeta Cheese and a side of Contaminated Tank Water

At this point, we were also waiting on a significant Western Union transfer and money was running out. We had just enough money to take a taxi to town but not enough to get back if the money turned out not to be there. Hence how Paul got parasites! We were almost out of food/water and he oh-so-generously gave me the last of the water and opted for tank water (we do not recommend doing this at all!) for himself.

Anyway, one day… we’re so freakin’ hot, tired, hungry, thirsty, you-name-it. We decide to walk to the cliffs about 1-hour away in the hot sun to get a small snack with our pocket change. We walk, and walk, and walk down these dusty roads sans shade for what seems like forever. Finally, we find this shack that’s selling bread and cheese sandwiches which is about all we could afford.

We get our bread/cheese combo and decide to walk the extra 15-mins to this popular beach resort where it’s free entry. You can literally hang by the poolside or spend the day jumping off the cliffs without paying a cent. So, we take our bread… which turns out to be cinnamon bread (gross!) and a hunk of Velveeta cheese and get on our merry way. Of course, you can’t go to Rick’s Cafe and NOT watch the sunset. So, we stay till past dark.

rick cafe, living in Jamaica, orange hill, sunsets

Here’s the problem. When you’re out in the middle of nowhere, it gets freakin’ dark… FAST. Remember that hour walk? Yep. Did that in the dark. And, of course, what’s a good nighttime walk without a straight up downpour? We literally had to hold hands to know where each other was. We had a camera which we kept taking photos (with flash) so we could stay on the road without going astray. Eek!

Halfway through our walk, the rain stopped, the stars came out, but we’re getting kinda paranoid. With the stars came these weird red lights that looked like a cigarette butt moving through the bushes. Was someone following us? They’d be sorely disappointed if their intent was to rob us. Ha. Anyway, this went on and on and on. Eventually, we were close enough to the house that we made a run for it.

As we caught our breath heaving at our front door we realized it was a form of firefly. A crazy red firefly that left a trail behind it. Whew! Don’t get me started on the freakin’ bugs in Jamaica. All you need to do is a quick Google search for ‘40-legs’ and you’ll know what I mean…

Meeting Franky While Living in Jamaica

While living in Orange Hill, we didn’t have internet so we’d walk 30-minutes downhill to the beach where we could buy a soda and steal WiFi for a few hours. This spot was so out of the way that we’d be the only people there aside from 1-2 guests a day. Typically, we’d have the entire place to ourselves. Anyway, sitting there one day our neighbor whom we’ve never met started chatting us up and offered for us to come to her house for a party that very evening.

Normally, we’re pretty freakin’ anti-social but the fact that we were living on near nada for food at this point our bellies happily accepted the invitation. Little did we know what we were getting into. We arrive and could instantly smell the plentiful supply of food. Lobster pasta. Fresh salads. Potato salads… all the goodies you can imagine. Our jaws hit the ground, we salivated, we wondered how soon would be too soon to jump on the pile of food.

With all our might we opted to wait until the crowd was summoned. As we waited, we met a Canadian expat named Franky. He was as authentic Italian as you could get. Oh, man. Later we learned his story… he was in permanent crutches after being shot 7 x by the mafia (!!!). Anyway, our first time meeting him he handed us each a giant spliff. Turns out, this wasn’t your average Jamaican weed. This was full-blown Canadian cush grown in bat shit in caves in Jamaica. We were floored.

Living in Jamaica, buffet party Orange Hill

They announced food was ready and we literally couldn’t move after two hits. We watched people getting up, filling plates, and salivated until we could muster enough courage to get our butts out of our chairs. Then, WE ATE. After sobering up a bit, we chatted with Franky and learned a bit more about him. He offered to cook us a meal at his house which we of course accepted.

The next day we met him outside this gated bar. He picked us up and we pulled into the parking spot next to a bunch of Hummers, Audis, etc (essentially cars nobody can afford due to import tax) and walked into the beachfront bar. As we walked up, we noticed everyone staring at us. The music changed. People were kicked out of their table and it was readied for US! What?!? This dude had some clout.

Almost everyone in the bar came up to say hello and pay their respects. It was insane. He handed out joints like they were candy. Upon leaving, Franky got up and started to walk out. We said we still needed to pay. He looked at us and said “We don’t pay here.” all matter of fact and we left. Whew!

He then drove us to his house. Along the way, we stopped at about 3-4 peoples houses where he dropped off formula/diapers/whatever for mothers. His house was gorgeous. Franky loved to carve wood sculptures in his free time and his house and workshop was evident of the fact. He cooked us an amazing dinner and we talked half the night. One of the best pieces of advice we got from Franky as to do what you want when you want. His motto was “I eat when I want, I fuck when I want, and I sleep when I want.”

Getting Back to ‘City Life’

While living up in Orange Hill, we met some interesting characters. One being our good ole pal named Screw. He was a bushman that would come by and sell us coconuts or offer to cook us lobster dinners or whatever else he could rummage up. We could never understand a word he said so we’d always just kinda mumble whatever and he’d show up the next day with whatever it was he had to peddle and we’d accommodate when we could.

Decisions, decisions. We were paying $200 a month to live in a shack. This shack though had million dollar views and was only a 30-minute walk to some of Negril’s hottest tourist attractions. We did share the property though with someone who was always either high or sick. Tough decision. After a couple of months, it just got to be too much and we moved on.

Althoug we didn’t have a ton of cash (or much at all…), we decided that our time living in Jamaica wasn’t over yet. Because our digital nomad life hadn’t exactly taken off yet, we were left with an extra laptop that we barely used. So, naturally, we took said laptop and a few other random knick knacks to a local consignment shop with the hopes of getting enough cash to rent another spot for a month or so. 

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