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As the months drag on with the COVID-19 pandemic, life has become a waiting game to get the vaccine, emerge from lockdown, and ultimately for the new normal to arrive. One aspect of this new normal for most who work in a corporate environment is working from home. And for some, working remotely doesn’t have to be from their home office or dining room table in their home country, especially now that remote worker programs are popping up all across the globe. There are currently nine digital nomad visa programs in the Caribbean, and more are sure to follow. With that in mind, here are ten tips for remote working in the Caribbean.

The curve of Carlisle Bay in Barbados. Photo Credit: © Barbados Tourism Marketing Inc. The curve of Carlisle Bay in Barbados. Photo Credit: © Barbados Tourism Marketing Inc.

1. Assess Whether You Have What It Takes to Live Abroad

There is a myriad of reasons to move abroad. These include experiencing life outside of your home country, advancing your career, learning a new language, experiencing new cultures, and developing new social skills. On the flip side, there are challenges. Moving aboard can be highly stressful, especially during the middle of a pandemic. Thus, it is important to make sure that you are moving aboard to work remotely for the right reasons and you have the right mindset, including a go with the flow attitude.

With that in mind, here are some questions to ask yourself as you decide whether or not to pursue working remotely in the Caribbean.

  • What is your primary reason for wanting to work remotely in the Caribbean?
  • What sort of lifestyle do you aim to have while working remotely?
  • Do you have the self-discipline required to work remotely in a foreign country, potentially having to navigate different time zones?
  • What are your home comforts and luxuries, and are you prepared to go without them for an extended period of time?
  • Are you open to making friends and socializing with locals?
  • What do you want to accomplish during your time abroad?
  • Will your finances hold up from working remotely for a year or more?
  • Are you ready for the adventure and even uncertainty that comes with living abroad?

Your honest answers to the questions above will help you determine whether or not you want to pursue working remotely in the Caribbean or elsewhere in the world.

2. Thoroughly Research Your Preferred Caribbean Destination

Once you’ve decided that you have what it takes to live abroad, would recommend researching and comparing the Caribbean digital nomad visa programs for remote workers. Here, it is important to look beyond the picturesque beaches and tourist attractions and really factor in things that will impact your remote worker experience, including airport access, cost of living, healthcare system, and culture plus lifestyle.

• Airport Access
Will you need to fly back to your home country regularly while working remotely in the Caribbean? If so, you will want to select a Caribbean island with multiple regional and international flight options. Keep in mind that most airlines are not currently operating at total capacity.

• Cost of Living
Most of the programs for remote working in the Caribbean require at a minimum, an annual salary of US$50,000 to ensure that people under the program won’t become a financial burden on the local government and can maintain an American/European standard of living. As a starting point, I would recommend checking the cost of living at websites like Expatistan. For example, below is the cost of living information they provide for Barbados, which was the first country in the Caribbean to launch a digital nomad visa for remote workers officially:

o Single person estimated monthly costs: US$1,611 (BDS 3,256)
o Family of four estimated monthly costs: US$3,784 (BDS$7,648)

As the cost of living will be different depending on your family situation (solo, couple, spouse with children, etc.), I would recommend putting together a personal budget to determine the cost to rent an apartment or house, and monthly spend for utilities, phone, internet access, food, transportation plus entertainment, etc. Here, it is best to start with a local real estate website as most now provide additional insight on living in the region. Once you have a low and high range on what things will cost, be sure to add to the budget any bills like student loans that you will need to continue paying in your country of origin.

• Internet Connection & Co-Working Spaces
Fast and reliant Internet services are key to becoming a successful remote worker. Thus, you’ll want to make a note of the internet service providers in your preferred destination and do a quick scan of reviews. If your job requires Internet access with speeds of 100Mbps or higher, I would research to discover co-working spaces. All Caribbean destinations will have a mix of private offices, hot desk spaces, and other co-working alternatives like Bermuda, the second Caribbean destination to launch a remoter worker program. Co-working spaces can be booked by the hour, day, week, or month. The benefits here go far beyond access to high-speed Internet but the opportunity to connect and network with other remote workers or locals who are self-employed.

• Healthcare System
Healthcare systems all across the globe are currently under strain due to the global COVID pandemic. Thus, if you have pre-existing medical conditions that will require regular treatment, chose the Caribbean destination with the most advanced healthcare system for your budget. For example, the Cayman Islands which launched its digital nomad program in October 2020, has state-of-the-art, modern medical services at eight locations on all three islands, including the 124-bed hospital in Grand Cayman and the 18-bed hospital in Cayman Brac. However, the income criteria for their digital nomad visa is US$100,000, so it may not be workable for everyone. That said, all the other Caribbean islands have reputable clinics and a hospital or two. So explore the options for each and be sure to get adequate medical insurance, including medivac to neighboring islands or back to your home country.

• Culture & Lifestyle
Visiting a Caribbean destination for a few weeks is very different from moving and taking up residence as a remoter worker. Thus to avoid culture shock, spend some time researching and learning about the history of your preferred destination. Also, make sure that you have a good understanding of their way of doing business. Linked to this is their concept of time. If you are from the United States, Canada, or the United Kingdom, you are most likely use to events starting on time. But in the Caribbean, most destinations operate on what we call “island time” which can be quite delayed, especially when it comes to social functions.

Other cultural considerations include general communication style. For most Caribbean destinations, things are pretty casual amongst family and friends. However, when it comes to business and professional settings, the communication can be rather formal and rigid with links to processes and systems, often slow and outdated.

Speaking of outdated, some Caribbean destinations even have rules about what you can wear when entering government buildings. One example is women not being able to wear sleeveless attire, which is total madness considering how hot it gets in the Caribbean. To avoid culture shock, it is vital to spend some time up front learning about the local culture, focusing on the positive, and going with the flow attitude.

So be through with your research, checking official government websites, local newspapers, and blogs.  Once you have a handle on airport access, cost of living, internet access and co-working spaces, the healthcare system as well culture and lifestyle, you are in a position to compare the destinations and make an informed decision on where you’d like to work remotely in the Caribbean. So get cracking with applying to the Caribbean digital nomad visa program of your choice.

Friends enjoying a fish fry in The Bahamas. Photo Credit: © Bahamas Ministry Of Tourism. Friends enjoying a fish fry in The Bahamas. Photo Credit: © Bahamas Ministry Of Tourism.

3. Review International Banking Options & Tax Liabilities

Beyond putting together a detailed budget as outlined above, you will need to give some thought to how you plan to move money between countries as you will be dealing with different currencies and banking fees that can quickly add up. To minimize money lost due to currency fluctuation and banking fees, I would recommend pulling together a few documents to help set up a local bank account. This includes getting a letter of reference from your current bank and at least three to six months of statements.

Also, consider setting up an account with an international money transfer provider like Wise (formerly TransferWise)  who markets itself as being eight times cheaper than using your regular high-street bank. Once you transfer funds into your account, you can then use their card to make local payments. Behind the scenes, Wise automatically converts the amounts for you, to ensure you get the cheapest conversion fee. Should note that I’ve also used Wise to pay for service providers in other countries (for example paying one of my web developers based in South Africa). That said, whether you use the Wise card or another credit card, always pay in the local currency to avoid hidden fees.

Regarding taxes, all the Caribbean digital nomad visa programs exempt successful applications from paying income tax. You will, though most likely, still be liable for taxes in your home country. For example, a United States citizen or a resident alien living outside the United States is still subject to United States income tax on their worldwide income. So would recommend speaking with your accountant and tax advisor to ensure compliance while abroad.

4. Visit Your Healthcare Professional For Pre-Departure Check-up

One of the most important things to do before departure is to visit your various healthcare professionals. This includes visiting your:

  • Doctor for a complete physical and general check-up
  • Dentist for teeth cleaning and to take care of any cavities, root canals, etc.
  • Optometrist to secure up to date prescription for glasses and contact lenses
  • Specialist travel clinic for any vaccinations; check requirements at Travel Health Pro
  • COVID-19 Testing Center as most destinations require a negative PCR test

With all of the above, you will want to get printed copies of your records to have on hand should you need to visit a doctor while abroad. You should also get a supply of any medications for at least three to six months. With medication, ask your doctor to note the generic name for any prescriptions. You will, of course, be able to get access to medical services while working remotely from the Caribbean, but as most healthcare systems are currently strained due to the GOVID-19 pandemic, it is best to have things done in your home country. A final note on the healthcare front is to ensure that your medical coverage is international and comprehensive with minimal exclusions.

The main entrance to Health City Cayman Islands Hospital. Photo Credit: © Arousta via Wikimedia Commons. The main entrance to Health City Cayman Islands Hospital. Photo Credit: © Arousta via Wikimedia Commons.

5. Update Your Electronics

The two most essential pieces of equipment you will have as a remote worker are your laptop and phone. Thus, I’d recommend having a technician review and optimize both. Heck, depending on your current equipment’s age, you may want to purchase a new laptop and phone. Also, you will want to pack a:

  • Second laptop or tablet as back up in case your main one fails
  • External hard drive to back up the data on your laptop
  • Spare laptop power supply, USB leads, and earphones
  • Portable laptop stand to help maintain good posture while working from different locations
  • A second phone, ideally unlocked so that you can use it with a local number
  • Portable chargers for your phone
  • Surge protector to help prevent any voltage spikes that could potentially damage your electronics
  • A couple of power strips as some rooms may have limited power sockets
  • Power converters

Besides the external hard drive above, I’d also recommend backing up your data in the clouds (Apple Storage, Dropbox, Google Drive, etc.). So if your laptop and external hard drive fail, you have a third source and can easily migrate your data. That said, you will be able to purchase all of the equipment above in your destination of choice, but supplies will be limited, and the price will be higher. So better to come with the equipment, you require along with backups to ensure that your work is not interrupted. Finally, make sure that your travel insurance from a company like WorldNomads covers damage and equipment loss. It can get rather expensive to repair or replace all of your tech gear simultaneously.

6. Shop & Ship A Barrel

As your time away for the remote worker program will be at least a year, I would recommend shopping and shipping a barrel or two with some of your favorite treats; non-perishable goods that are unique and would be difficult to find in a foreign country. Along with a few of your favorite treats, you will also want to include in the barrel some household and personal items that will help make your stay in the Caribbean a comfortable one. For example, if you use shampoo or beauty products that are only sold through a particular store, add a few bottles to the barrel.

Should note that shipping barrels to the Caribbean are pretty standard. When visiting family during the holidays, it is common to ship a barrel in advance of the trip. It usually takes a month or so, so you wouldn’t want to include items you will need right away. Again, nothing that is perishable. To find a suitable company, just Google shipping a barrel from your city to country where you will take up residence as a remote worker. For example, shipping a barrel from London to Montserrat takes about three weeks.

Gary Morton working remotely on Caribbean Island of Montserrat. Gary Morton working remotely on the Caribbean island of Montserrat.  Photo Credit: © Montserrat Tourism.

7. Book Suitable Accommodations

Finding suitable accommodations will be one of the most important decisions, and so best not to rush the decision. I recommend deferring the decision on where to live until you are actually on the island. To start, just book a hotel room or Airbnb for at least the first two weeks beyond any quarantine period. This will allow time to move about the island, visiting at least three different neighborhoods and, at a minimum, double the number of properties with or more real estate agents. In terms of area, select one that is central with easy access to public transportation and shops if you will not be leasing or purchasing a car to get around the island.

Living in a more built-up neighborhood will be more expensive than an apartment or house in the countryside, but it will be easier to reach the city, shops, cafes, co-working spaces, restaurants, etc. All of these are important to enjoying the destination and ultimately connecting with other expats and locals to form friendship groups. So once you settle on a neighborhood, book an apartment or house, ideally on a short-term lease, for, say, three to four months with the option to extend or move on to another property or neighborhood. Depending on the island’s size, this would be an excellent way to explore and get to know the whole country.

8. Eat & Drink Local

When moving to a country, immersing yourself in the local cuisine will enhance your experience. Plus, there is no point relocating to the Caribbean if you are just going to eat American or European cuisine. Your food bill will get rather expensive as most of this food is imported and you will just be missing out on all the delicious local dishes. So I would recommend taking a food tour to sample the wide range of local cuisine with an expert who can provide history and insight. Another option to help you acquire a local palate is to take a cooking class to learn more about local herbs, vegetables, and ingredients, along with ways to prepare the national and other popular dishes.

A visit to the fresh food and vegetable market (also fish and meat market) with a local guide is also a wise investment. The local guide will educate you on all the “exotic” products you may not be familiar with, and they can also point out the best vendors based on products. Beyond the markets, they will also be able to point out the best local supermarkets. Where possible, you want to stay away from those catering primarily to expats as they are sure to be overpriced.

Tasty Caribbean Food stand in Antigua. Caribbean fruits and vegetable stand in Antigua & Barbuda.  Photo Credit: © Ursula Petula Barzey.

9. Maximize Your Stay

Once you are on the island and have sorted your accommodations and stocked the fridge, it is important to get into a new daily routine with a focus on achieving work-life balance. So developing a schedule that includes time for exercise, exploring your new neighborhood/country, meeting new people and of course, being productive with work! With regards to building up your network with new friends and acquaintances, link up with a local expat group as not only will you be able to meet new people through their events but they are also a great resource for news and information that affects foreigners.

Also, connect with local clubs that focus on an activity of interest. For example, a running or hiking club, perhaps even a local charity. Important here is that you not only make an effort to become friends with fellow expats but also connect with locals so that your experience on the island is as authentic as possible. As such, from the moment you land, make an effort to having engaging conversations with the locals you interact with starting with the taxi driver from the airport as they are extremely knowledgeable about the island and can provide recommendations on where to live, places to shop, eat, service workers, etc.

10. Stay Connected

While it is important to immerse yourself in exploring your new country and making new friends and business contacts, it is also important to stay connected with family and friends at home. The great news is that there are lots of apps you can use to make this happen. For example, I often speak directly with family and friends in the Caribbean using Facebook audio/video feature. Similarly, I use apps like Skype, WhatsApp, and now Zoom to help maintain long-distance relationships.

Another form of connection is starting a blog or documenting your time abroad via social media channels like Facebook and Instagram. A blog with detailed posts about your activities abroad would be great, but it can also be time-consuming. So if nothing else, consider sharing some of your images via the social media networks mentioned. Whatever you decide, embrace the experience to the fullest. Also, resist the temptation to compare your new life with the one you left behind. Things are bound to be different (especially with the COVID-19 pandemic), so follow the guidance above to select the Caribbean digital nomad visa program that is best for you. Living abroad is a lot of fun and there is no better place to do it in the world than the Caribbean, provided of course you have realistic goals and expectations.

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UPB at Antigua Carnival 2019.
I'm Ursula!

Welcome to Caribbean & Co. founded by Ursula Petula Barzey who enjoys traveling the Caribbean in search of the best cultural and food adventures, places to stay and live/work opportunities. Launched in 2014, Caribbean & Co. has won five travel media awards.

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