
Jamaica is a very interesting travel destination for workations. This time my companion from the Hookah club joined me, so we had both workation and offsite hookah club meeting, music inspiration trip and joy of free roaming. Lotâs of media, so please donât forget to press those play buttons as you see them.
Montego Bay
Montego Bay - Day 2
Jamaica is different. You donât get rental car insurance coverage with your credit card, neither Amex nor Sapphire provide that. Itâs on the list of exclusions among another 3 countries worldwide. For some reason, all of them have the steering wheel on the right side of the car. Another thing to be thankful for to the Queen.
The moment weâve exited the terminal with car keys in hand, happy and relieved of the fresh air and jungle nature, people started actively selling weed to us. Not just like âhey, want some?â, but âI invite gentlemen to take a look at my connoisseur selection of Jamaican finest.â Gentlemen know that buying weed right outside the terminal is not the best idea, so we took a car and drove to get coffee first. These red-eye flights keep people tired.
The moment we found the parking near the coffee shop (which served coffee from the coffee machine with one option as it turned out), another gentleman approached with great vibes and chill, asked if we needed some, because he just rolled a bunch in the morning and was going to smoke one himself. This time, the charm was irresistible, so we bought a joint and finished it on the location. $10 bucks per joint, California prices one could say.
Still looking for the coffee shop, we stopped by the Island Flower dispensary and checked how that experience is different from US dispensaries. As you guessed, the selection is thin, although most of the offerings are available: edibles, pre-rolls, vapes, flower, you name it. The price for the premium product is twice as much as on the street, although mid-shelve matches the street price. The store has a special area where customers can use the product without disturbing the environment while listening to reggae music and chilling on a comfy bean-bag. We were getting a vape and suprisingly, the salesperson insisted, no, demanded us to try the product after the purchase before leaving the store to ensure the proper quality and workmanship. I was like âplease, I just finished the joint, itâs okayâ. Salesperson insisted and I was not here to kill the vibes, not that they ask to do something illegal, right?
Obviously after this endeavour we completely forgot about our desire for coffee and decided to go for a walk in Montego Bay Hip Strip. An AI would probably autocomplete here âwhich is a famous tourist destinationâ, but itâs not. Although having positive vibes and chill people, the environment looked sketchy. The combination of poor infrastructure and not maintained buildings contrasted on the background of high-end malls that were either renovating or empty. It was painful to see so beautiful place so neglected.

After walking it off for a while we had to drive to checking into our AirBnb. The moment we landed in our car, torrential rain poured the streets. Water flew from every corner, regular puddles turned into small lakes, so driving was even more exciting. Remember the right wheel? Yeah, itâs not difficult to get used to driving like that. Itâs just feels wrong all the time.
Turned out our AirBnb was located in remote area for rich people with private security, gated checkpoints, private beach, all the jazz. That was a very nice change as we got to appreciate the combination of nature and modern Jamaican architecture that was not neglected.

Itâs difficult to not love the nature when living in California, you really canât get that love behind, you canât unsee all these beautiful trees, flowers, birds everywhere you look, and Jamaica has so much to see. That private beach sunset that I captured was one to remember, lightnings on the other side of the horizon were majestic, breathtaking, powerful and not captured on the picture.

Walking to the beach Iâve noticed the advertisement sign on the electric pole. We lend you 50,000 in 30 minutes. Wow, nothing interesting about that, right? Although coming back from the beach there was a different number on the flipside: now itâs half a mil in 24 hours. Apparently the amount of money is available to the population depends on the direction they are walking.

So Montego Bay left that feeling. The combination of rich and poor, beautiful and neglected, chill and sketchy, town and country, nature and concrete is organically merged beyond our comprehension.
Road Trip to Negril
When taking workation road trips itâs usually very useful to have a plan where to work: inspiring place with reliable internet connection. For once I can recommend Sky Beach. We arrived before the opening yet they let us in and provided the wifi for 3 of my back-2-back meetings, while also feeding the most delicious Coconut Curry Red Snapper. âď¸âď¸âď¸âď¸âď¸ hands down, highly recommended spot if youâre in those locations.

Suddenly, when the meetings are over, weâve reconvened about all those zoom-people that we met who were sitting in the office. Sadly no company is providing the benefits to work nomad-style for one week per quarter, although it could boost a lot of productivity over the globe. Workations could be a good perk of the future.
The rest of the road was smooth driving above the ocean on one side and below the mountains on the other.
Negril
Tree House - How did they do it?
Negril is magical. I donât have enough space in this blog to describe the spiritual experience I had in this place. Imagine going on an intensified adventure cleansing head and body. The vibes of the resort area facing West. Stunning sunsets and scattered jungle alongside the curvy roads. We stayed in the Treehouse which seemed to be specifically designed for people to have a dialog with inner self. My bedroom had a ceiling on the arms length when I in bed. The AC was blowing the insects away from their tree, while I was occupying the natureâs territory. Nature was not against it, just had itâs own opinion.

First, I thought itâs a lighthouse above the cliff. We thought that the ships would stop in the natural harbor by the lighthouse. The water below was so clear that it took us a while to realize that it goes beyond reason: a little submarine would be able to park near it. It was a tower! Having two kids makes you think twice before jumping from the tower, so we jumped from the cliff where it stands, maybe 20 feet above. This activity has hidden benefits to short and long term mental state.

Unimaginary happiness and calm is in the deep. The moment tranquility wraps your body and mind. You are not descending in the water any more, yet not ascending to the surface either. The sound of water and bubbles fades, you stay in total silcence, canât even feel your pulse. Clock skips the beat, and you have those truly for yourself. The moment your head goes above water your body indicates its battery recharged to 98% immediately with .5% every second for the next 30 seconds.
These experience lead to extraordinary work results. Officially the most productive workspaces known to humanity (represented by my humble persona) are on the picture below both competing for the first place: table inside or table outside.

At some point, when the meetings stop creeping into my day, I decided to do âsome serious workâ and sat on the table inside enjoying the mango-carrot-coffee-tonic. That was supposed to be a 2 hours uninterrupted pomodoro run. After 10 minutes I was done for the day. I did everything I had an ambition to do at work, successfuly overcoming all the issues.
To prove my hypothesis about productive workplace, I started writing this blog. The text from the top to this moment you are reading was written on the table outside in a short burst of creative inspiration that felt less than 10 minutes, so I dedicated the rest of day to jumping into the water and staying in that tranquil weightlessness in the deep.
The treehouse felt transcidentally ayurvedic. It felt like master, guru, teacher, witchdoctor were all nearby, but didnât expose themselves not disrupt our attention to healing the decayed corporate souls.
Captain Tj
Workation progressed into vacation for the last two days of the week and we found ourselves in one of the Negril hotels that are tighly located on the 7-mile beach. The boat was not that far from the spot we were letting our bodies soak in the sun to better process spanish omelette. Captain Tj and his âFish Finderâ were interested in getting additional income out of these few tourists populating the region in October, so we signed up for the snorkeling session on the reef, which captn knew like palm of his hand. Upon agreeing on the numbers and tender, captn disappeared somewhere rapidly while we were still processing spanish omelets by the boat now. His excitement was overboard when he returned and showed a couple slices of bread that he pilfered from the hotelâs kitchen.

Once we were at the reef wearing the masks and the fins in the water captn handed over a slice of bread with âoff you go now. đđż wayâ.
As in every good story, the narrator has something to confess: Iâm a crappy snorkler. The water fills my tube, I try to spit out the salt from my mouth, while I was in my misery with the watersports, Zebra-like fish (Captn called it Sergant Major because of the stripes, I guess) was already eating bread I was holdingin my hand! I forgot to breathe for a bit while looking at these tiny little cute creatures having a snack. Then the water got into my tube again, I felt that salt on the tip of my tongue, one of my fins was gonna go loose, so I decided itâs time to get back on the boat.
Captn Tj was not a big talker and didnât have a lot of pirate stories to tell us. The joint never left his mouth, so it was quite difficult for him to talk much. Nice excursion ride alongside the 7-mile beach was a cherry on top and a good start of the vacation part.
Road trip to Treasure Beach
This time we took the road closer to the mountains, although still seeing the ocean from afar from time to time. Reggae out loud, itâs our fourth day on the island, it doesnât feel that other cars are just trying to crash into us. While our minds were entertained by a discussion of global economics or technology, the dump truck shows up from a sharp with the intention to check if the road is better on the other side, so I take a little left, catch a pothole and in 20 second my front left is flat. Itâs round 3pm, thermometers are reaching for their daily maximum and the wind is nowhere to be found.
One of the passing drivers sees our pitiful attempts to bring the car up with the jack. He stops, gets the jack out of his car, gives the rental to us with disgust, lifts the car and changes the spare tire. While doing so he talks to us about, but we cannot understand a word. Without asking how much I had him the USD and he says that the tyre shop is conveniently around the corner, they will patch our tyre in no time.
Indeed, the tyre (I know, itâs just what was written on the shop, Tyre, keeping it true to the land) was replaced by young gentlemen of the shop. We were convinced to have another dialog about Jamaican finest selection, but this time it was different. For the hour that the repairs were going we were listening to 10 different reggae covers of Ave Maria and the guys didnât even pause for smoke.

Jamaican men can be rarely seen without a joint in the wild. They are either actively smoking it, holding in the mouth the short butt of whatâs left or a new one that they forgot to light up. On rare ocasions lucky tourists can see a joint above the ear as well, but they donât stay for long there.
While the jamaican women are hard at work. Kitchen, serving tables, cleaning rooms, thatâs where you can usually meet more women than men tourist destinations. The only thing I didnât see women do is selling weed in Jamaica. They did all the rest of work: security guards in the airport, shopkeepers, hosts, almost everything. Jamaica runs on women.
So the New Hope suprised us a whole lot. I guess it has something to do with that Ave Maria and Christianity that was in the air.
Treasure Beach
Southwestern (more southern really) town Treasure Beach was way less touristy than Negril. We arrived later because of the incident, the dinner time shifted past sunset while we were stuggling to find living souls in the town. Everything was closed. No, closed doesnât cut it. Shut down. Everything was shut down. As if the life stops and there will be nothing until January when the season starts. Only Buddha was patient enough to wait on the spot.

We found the only opened diner in the town where among 9 menu items only one available: fried chicken with rice and beans. Not having any other options is a very limiting condition. But damn that chicken was good! Hunger is the best sause, they say, but this chicken fried to perfection: crispy, juicy, flavorfull. A meal to remember.
Meanwhile, the radio receiver started repeating the same set of sounds over and over again. It caught our attention after the third loop and we started listening carefully to the message that stated:
- This is not a drill
- Storm is coming
- Secure your belongings, houses, essentially get your shit in order
- Evacuate on higher ground
The locals that were picking up the food from the restaurant were in the hurry, the shopkeeper asked if we want to buy anything as she had to leave and will be back in an hour. We were good, but the locals were a little tense as it seemed.
Thatâs how Melissa joined us on the trip. First, we shrugged and decided to walk on the beach in the evening, find that only beach club Lashingâs that was open. The night beach was dark and volumetric as waves were blasting into the stones scattered across the laguna. Everything was closed and dark, so it was not that difficult to find the club. We didnât have to ask twice if we were on the spot as a joint family of Brittish and Jamaican (around 10 people including kids) telling hunting and fishing stories over drinks and marijuana. It seemed that they were ready to leave, but were pretty chill.
Totally different vibe from the chicken store. So after having those virgin daiquiries and pina coladas we went back to the AirBnB to close the night.
It was obvious that the only place to find breakfast would be the exact same beach club. As we reached it around 10:30am, people were already packing up the bar, equipment, taking down decorative shades and securing the place for good. They couldnât refuse so charismatic customers like us in breakfast while telling us a story about last year hurricane tha destroyed 70% of roofs in the area and these things are no joke. As we googled up what is going to happen, our trip went through rapid gear shift, we modified our plans, changed the Kingston returning flight back to Montego Bay, jumped on the ocean waves for a bit and drove away.
Although the hurricane will make a landfall on Monday, Kingston airport is already closed, Montego Bay airport is closing Sunday noon and another missing tourist is not going to help people of Jamaica to weather the storm that is coming.
Way Back
Evening troubles
After a couple startcraft 2 matches the time was nigh for us to leave. We decided to take a mountain road across the island to see how things are in the jungle. That was a terrible choice that we fully enjoyed. Besided the road being very steep in the mountains, it was narrow so that most of the time you had to drop to 20kmph to clear the oncoming traffic. Potholes in the most unpredictable places. Sometimes filled with rainwater so you donât know how deep they go.
I was lucky to get my driving experience from ukrainian roads and managed to squeeze a lot of fun from that driving. Itâs not your lazy 82 miles per hour on 101 barely holding the wheel, but two-arms exercise for attention, dexterity and endurance. There were moments when I almost jumped out of the seat (and maybe the car as well) as 40yo Ford F-350 spawns behind the hill on no less than 50kmph and you feel a little scratch on the ear.

Unplanned return to Montego Bay was successfull.
We sealed the trip on our last night in the same hookah parlor we opened the workation. We hopped on the same Blue Infinity and Beyond jet and are safe and sound now.
This experience was absolutely improvised. We landed with only one AirBnb booked. We had a short list on the locations that we wanted to visit and visited them all except Kingston. We had a long list of work tasks we planned to finish and accomplished even more than anticipated. We had good conversations in the hookah and restaurants, soaked on the beach and in the water, slept on the ground and on the tree, reached to the depths in the water and into oneselves.
I hope Jamaicans will be spared and Melissa doesnât damage this beautiful island. I hope Jamaicans will smoke less and do more. I know that Jamaica changed my perception and I know how to become better.
