how to get a job in the caribbean

Caribbean island jobs in 2 months

When we first started looking for Caribbean islands jobs we had no confidence whatsoever we would get any. Living in paradise was never on our mind when we started our travels by moving to London to get hospitality experience.

I still remember when we did a google image search of the islands we thought: no way we will land any job in this place with almost no experience and money.

But lo and behold, almost two months after landing in paradise itself, we were legally working and enjoying the best time of our lives

When we landed in Georgetown, we had nothing but the first few days of Couchsurfing booked, and a huge baggage of hope

18 months later we had an amazing group of friends, the confirmation heaven does exist, and a good sum of money on our (offshore? we wish…) bank account. Couldn’t have worked out any better.

Do a image google search for Cayman Islands and this is what you see

Want to get help finding a job in the Caribbean? Click Here 

Cayman Islands jobs in hospitality

When living in London a friend told me that the best way to make money and travel was to to go to Cayman Islands and get a job in the hospitality sector.

And I looked at him and asked why? He told me it was easy to move there, you could earn a lot of money with tips and no taxes, and half of the population was already foreigner so easy to adapt. 

He is Jamaican, a neighbouring island, and Cayman Islands is where Jamaicans go to get better life conditions, hence his advice. 

Nonetheless, we did research other options. The Cayman Islands is one the most expensive countries to live in, which initially made us think that it could be a bad idea. 

There were other options like British Virgin Islands or Bermuda (even more expensive), and if you look on websites like Island Jobs, there are almost 20 destinations where you can find jobs. Don’t forget to tell us here what job you are looking for. 

But for everything that we researched online, the Cayman Islands was a consensual preference, and soon we started to narrow down our search. 

We spoke with many people about Caribbean islands jobs, people that had been in different islands working not just in hospitality, and we got even more reassured we were doing the right thing. 

We concluded that these islands offered us the best balance between lifestyle and income which could allow us to live for a longer period than you normally would if only money was relevant. 

When working just to save money without a balanced lifestyle there is a limit a person can withstand, maybe 6 months if you are on a cruise ship for example. But, if you manage to balance money and life then it’s perfect. That’s why it was so hard for us to leave the island as we were so comfortable and happy.

cayman islands beach life work jobs caribbean
This is what we call a balanced lifestyle. Wake up every morning and have time to enjoy our almost private beach...

How to look for bartending jobs in the Caribbean

While it is common to find a bartending job in the Caribbean before traveling there, it is not as easy as if you are an auditor or work in finance.

In our case, we had just about a year of experience working in bars in London and an official diploma from a bartending school. 

We knew that work in the Caribbean is very different from London, although Cayman Islands is part of the Common Wealth, a British overseas territory.

Despite our personal experience of going with empty hands, we still recommend you try the online job boards first

Many websites like Islands Jobs or Caribbean Jobs will offer you lots of options for jobs, but specifically for the Cayman Islands hospitality jobs you can also check the classifieds page called  Ecaytrade.

bartending cayman islands jobs caribbean
Class of 2010 finishing our first Cocktail Bartending course

Getting to the islands and look for hospitality jobs

A very important reminder, before heading to the islands get a police records report. (CRB in UK and DBS in US)  I’ll explain why in the next chapter.

Get there

To fly to the Cayman Islands we normally used British Airways to Miami and then Cayman Airways to the islands. Qatar Airways is also an alternative we explored a couple of times when getting back from Europe.

Nationals from most countries traveling to the Cayman Islands do not need a visa, an automatic 30 days waiver is given as a tourist. (here are the exceptions to this visa rule)

This means that if you are not on that list then getting to the Island is easy, and you get a full month to stay and find a job. Remember this is a tourist VISA, you are not allowed to work with this.

You need to get a Visa that allows you to stay and live on the Island. You need a Work Permit, which will allow you to stay legally for the duration of the contract you get for the job.

Initial Savings – yes, you need some initial cash to buy your flight and live the irst couple of months in the Cayman Islands which is not cheap at all. 

We saved 6000 USD before we moved and it was about right. 

If you do not have that cash saved then consider doing a side job of teaching english online. The easiest way to make some money, follow our article here. 

Get a Job

It’s time to look for a job and you have exactly one month to achieve that. It’s a race against the clock, but we both did in less than a week.

The reality is that the Island is not that big, so you can visit all restaurants, bars, coffee shops in a week, use CaymanGoodTaste for all hospitality and CaymanBuzz for anything else.

cayman islandsa tourist jobs caribbean bartending hospitality
Although in this map it looks everything is spread out, most of businesses are on the East side

Also important is to be aware of the high season which starts in October, and this is valid for any jobs in the Caribbean. 

The best time of the year is to look for a job is a couple of months before the high season, like August/September, while the businesses are looking for staff. 

Get a home

Have also in consideration that accommodation in the Cayman Islands is quite expensive. For our first month on the islands, we used Couchsurfing to be able to meet local people quicker and of course to save on costs.

If looking for places to lodge temporary then Agoda has the best options, and the cheapest one is still Eldemire’s Tropical inn which offers rates below 100 US. Check also their webpage here for details.  

If you want a little more comfort and still want to stay on the budget (for Cayman Islands standards) of 100 US then head to Grand Camanyana, you will not be disappointed. 

Hot Tip: We also managed to stay in expensive hotels a couple of times by showing up late in the day and ask for specials. Every day, if the hotels have low occupation levels they open special prices, which works only on a daily basis.

In terms of income expectations have in mind that it will vary a lot based on the quality of the place, the location and the type of customers. American customers tend to be better tippers. 

To give you an idea, we made around 3k US dollars a month working 4/5 days a week. This is just a reference as it will all depends on the place you work and what type of tipping system they have, besides the other variables I said before. 

And also remember that there is no income tax in the Cayman Islands, all you make goes almost 100% to your pocket. There is only a couple of small deductions that have to do with health insurance. 

Even those deductions you can get them back as soon as you leave the Island, which means you get back the totality of your income. And this is an awesome feeling, to be paid tax free.

Not that taxes are not needed in societies, and we are more than willing to pay, but I personally have to admit I’m more in favour of higher consumption taxes and lower income taxes, but this is a theme for a book, not for a post. 🙂 

We did a video describing our experience moving to the Cayman Islands to try to win a tourism competition. We did not win but the video shows accurately what happened. Check it out:

What to do after you get a job

As soon as you get a place to work the clock stops ticking. It does not mean it’s all done and you can start to work right away, but it means you overcame the hardest hurdle and now it’s just a matter of bureaucracy.

It’s the employer responsibility to file your papers, pay the permit and deal with all the legal issues, including social security and health insurance. 

Remember I told you to bring a police record report? It’s now you will need it, which will speed up things a lot. We had to wait for ours being sent from UK which took weeks.  

Check the Immigration webpage for all the documents needed and also Cayman Resident for all practical information and updates. 

Bring what they require already with you to speed up the process. From entering the country until you have the permit approved can take up to 8 weeks

This means your 30 days Visa waiver will expire and your permit is not approved yet, you need to temporary leave the country. That’s why we spent 5 amazing weeks in Cuba while we waited for our Visa confirmation.

You will always have to leave because you need to have your work permit stamped on your passport, and that’s only possible when you are entering the country, not while you are in the country. Sounds silly, but that’s how it is.

Cuba is a very different side of Caribbean life, it's where Africa meets Caribe, explosive mix

Not everyone goes to Cuba like we did, especially because being so touristic is not the cheapest place to go, but anything is cheaper than the Cayman Islands, where it’s almost impossible to find lodging under 100 dollars a night. (with this exception)

After almost 5 weeks in Cuba, our paperwork was ready and we could enter the country getting the work permit stamp on our passport. 

This is when you look at your passport and you feel ecstatic because you can now live in paradise at least for a year, if you are not fired before of course. 

And after that year, you can extend your work permit, as long as your employer decides to do so. In case you want to change job it is possible, but not easy so think carefully about your decision. 

To a certain degree you are in the hands of your employer, as the work permit that he controls is your only legal support, but this does not mean you have no other alternatives. 

On the contrary, Cayman Islands jobs market is quite dynamic, so it is possible and not that uncommon to change employment. It will mean another red tape adventure, but sometimes you don’t even need to leave the island. 

So, if for any reason you are really unhappy with your job, then consider other options cause the hardest part is already done, you have a foothold on the island already. 

For us, everything went flawless, and we really enjoyed our life on the Caribbean. We often think about going back, but our life today is on a different stage, now we travel with a purpose of growth, for that we need new places, new stimulus. 

But to anyone that hasn’t been there yet, we totally recommend at least a season in heaven. 🙂

cayman islands jobs hospitality bartending caribbean
I was very lucky with my workplace as they trained us in many areas, like wine tasting which was awesome

Want to get help finding a job in the Caribbean? Click Here 

Get settled in the Cayman Islands

After returning to the Islands and have your work permit stamped on your passport you are ready to settle in

Start looking for a place to stay as soon as you get a yes for a job, which means even before you leave the island to come back later on with your stamped passport. 

Especially when costs per night in any hotel are so expensive that you really need to rent a place to live as soon as you get back with your work permit. Try to look for one close to your work so you may walk there instead of being dependent on a bike or car like we did.

Luckily, because it is a small country and island, information is very much concentrated and Ecaytrade is the place to go where you find everything you will need. Also check coffee shops for ads, that’s how we got our little heaven house.

We bought our bike second hand using Ecaytrade too, and found many of our house appliances there, it’s basically a craigslist. 

Ecaytrade is your main tool if you want to be as sustainable as possible and try to buy second-hand products, and of course, sell your unused items too. 

Also look for local Facebook groups with garage sales. It’s a very seasonal country, so a lot of people leave at the end of the high season, and they want to sell what they have. You will find amazing opportunities, even better that Ecaytrade.


cayman islandas caribbean hospitality jobs
Our windowed house 50 meters from the white sand beach

Another practical advice is about banking, even though the Cayman Islands are famous for the offshore banking, their retail local banking system is somehow behind what one would expect. 

We choose to use Butterfield Bank Cayman, and we had no problems whatsoever with them. But we were surprised how difficult it was to transfer money between local banks. 

So choose wisely and have in consideration the bank your employer uses, otherwise, you may have some headaches moving the money around. Yes, to transfer money between banks sometimes you have to do it manually, crazy I know. 

The branch we used was in Camana Bay, and that also makes a difference, as they will limit your actions base on the branch your account was open, it’s like the branches were individual banks.

For all this practical advice the best resource is Cayman Resident, we used it extensively when we moved to the Cayman Islands.

Wrapping up our specific knowledge with the following points:

  • Look for walking distances to your job
  • Check with your future colleagues
  • Coffee shops and other places with ad boards
  • Temporary lodging  Eldemire’s Tropical Inn or Airbnb
  • Garage Sales on Facebook
  • for second hand
  • Ask your future colleagues if selling (may be leaving Island)
  • Rentals, we used Andy’s but there are many
  • Get your CI Temporary driver license for 20US 
  • We used Digicel for mobile and land
  • There are only two companies, Flow and Digivel
  • Remember to properly cancel your contracts when you leave the Island, we had some extra costs to pay for not having more evidences
  • Many options in the Island
  • Check your Employer’s first. Use his Bank, will make your life so much easier
  • Also check different branches of the same bank, they have different advantages
  • We had Butterfield Bank, which worked like a charm
  • Get a postal box, there is no conventional postal service delivering to your address, you need to get a postal box
  • To get deliveries from abroad we used Shipito you will struggle to send anything from Amazon or Ebay to CI, hence the usefulness of Shipito

Welcome to Caribbean lifestyle

Exotic is synonymous of Tropical, and even though the word was coined in the middle of the 19th Century to describe the Middle East travels, it has now expanded to other tropical destinations where today also reflects the dream of a Caribbean life.

The Cayman Islands represents for us the quintessential modern tropical life on an Island. 

You can either have the beach/all-inclusive/party combo, although with budget restrictions as the Islands are the second most expensive place in the world. Or you can immerse yourself in the local Caribbean culture and have a comfortable and healthy lifestyle.

More famous for being a tax haven, we couldn’t desire a better lifestyle than what we had there, our small apartment was literally on the beach, which was as pristine as one can imagine and it was most of the time just for us. 

We were surrounded by water and beach life, and the weather was so consistently pleasant and sunny that it felt heaven would struggle to compete. (just need to be aware of the hurricane season during low season)

The slow travel approach we talk so much is the only way you can really go deep on the amazing Caribbean culture. It’s actually engulfing yourself in a lifestyle based on the sea and of course, some tourism. 

The Cayman Islands are so developed and populated by so many expats that it has created a bubble that floats above that native lifestyle. 

By living there for a longer period, and making an effort to explore you will discover the real tropical way of living. we’ve loved it so much that we’ve considered more than once the possibility of going back again.

diving from our own beach
Almost every day we went to check out the coral reef

The Cayman Islands are one of the safest countries in the world, it breathes a healthy lifestyle and has the best weather conditions we have ever experienced. 

Literally, one-third of the population is foreigner, and from that third half is from neighbouring Jamaica and the other half is mainly American, British and Canadian. Nonetheless, there are almost 100 nationalities living on the Islands so we always felt we were living in a very cosmopolitan place, of only 60 thousand people. 

Yes, only 60 thousand people, not even enough to fill a proper football stadium, which did create a good sense of community, although sometimes you felt the need to travel just to refresh your mind. 

And traveling is quite affordable if you go to Miami or some of the closer countries. 

And what kind of activities were available on an Island as flat as a pancake? Beach and water-related of course. 

We did our diving certification and we dove almost every week, which was just amazing. The clean and warm waters and absence of dangerous animals made the experience so accessible and enjoyable that even today we miss the Island just because of that. 

But there are many other sports available, I joined a local soccer team, played tennis regularly and almost joined a couple of marathons. Sara did yoga, photography field activities and even had time for some volunteer work with Red Cross.

The most striking difference from the life we had until that point was the pace of everything, Caribbean speed means one should not worry too much, just sit back and enjoy the ride. 

Still remember days I left work upset with something and got home to see our beach view and thought: “How can I dare to be upset…!!!”

caribbean jobs hospitality cayman islands

Want to get help finding a job in the Caribbean? Click Here 

Want to find about other kind of jobs or work oppurtunities to travel the world? Head to our working nomads resource page. 

This is very important, always travel with insurance, especially in a expensive country like the Cayman Islands. And no, you do not need to do lengthy travel insurances anymore, you can do by day with Safety Wing which is the best value for money you will find. 

3 thoughts on “Best travel jobs for Working Nomads: How to get work in the Caribbean islands in 2 months”

  1. Hey! With some experience to travel and adventure spirit, I am very interested in any opportunity that appears in the areas that you mentioned above. I would like to know how I could really take this forward, if there is availability , and if the things you provide are the ones mentioned above too. This is to say that regardless of time, I would find a fantastic opportunity if it were to happen.

    Best regards, Edilson Gourgel

  2. Thank you for delivering such informative info .Really appreciate your time covering so many beneficial topics about living working in the Cayman Islands

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Our Society is becoming Nomad again. Learn here how to become a World Citizen and live borderless

With more power, comes more responsibility. Learn here how to travel with a Zero Waste lifestyle