A solicitor’s guide to living and working in the Cayman Islands

A solicitor's guide to living and working in the Cayman Islands

The Cayman Islands. The best of both worlds. A place where you can get hands-on with some of the most complex and interesting legal work in the world, where you will be client facing and building contacts from day one, and where your prospects and earning potential are as good, or better, than they were at home. Add in the lifestyle advantages that come as standard in the Caribbean and it starts to sound too good to be true. So, is it?

The Island

  • Western Caribbean
  • 1 hour from Miami
  • World class financial centre
  • Stunning climate
  • Outdoor lifestyle
  • Upmarket tourist destination

Situated in the Western Caribbean, 480 miles south of Miami, the archipelago is comprised of three islands, Cayman Brac, Little Cayman, and around 90 miles southwest of them, Grand Cayman. Its nearest neighbours are Cuba to the North, and Jamaica, 167 miles away across the 18,000ft depths of the Cayman Trough. Administered by Jamaica until that island’s independence, it is now a British Overseas Territory. Its climate is a major attraction and with average temperatures ranging from the mid to high 20’s throughout the year it is easy to see why so many find it appealing. One word of caution though, with its tropical climate comes the annual Atlantic hurricane season – something which needs to be taken seriously, but which the islands have shown themselves to be extremely well equipped to deal with.

Despite its size (22 miles long by 8 miles wide at its broadest point), Grand Cayman offers a multitude of ways to spend your free time. Much focus is rightly given to its water sports – it is after all a world class location for scuba diving and sailing – but it also offers numerous other sports facilities, as well as the bars, restaurants and nightlife you would associate with a major upmarket tourist destination.

The Economy

  • Tourism and Finance
  • Lack of direct taxation
  • High average earnings
  • Global Hedge Fund capital

Tourism and Finance are the twin pillars of the Cayman economy and between them account for a large majority of the 90% plus of the employed who work in the service sector. The finance sector has grown rapidly over the last thirty years but perhaps the most influential development came in the early 1990’s when it instituted a new Mutual Funds law which – along with its favourable tax system – rapidly made Cayman the destination of choice for offshore funds. Whilst much copied, Grand Cayman retains its preeminent position in this market, registering its’ 10,000th fund in 2008.

Although the vast majority of goods are imported, making the cost of living high, the lack of direct taxation combined with high average earnings place the Cayman Islands near the top of most ‘quality of life’ charts. By some way the wealthiest population in the region, it enjoys a notably high standard of living.

“Climate perfect to enjoy a lovely outdoor lifestyle”

The Legal Sector in the Cayman Islands

  • Offshore legal sector
  • Cayman Islands common law
  • International client bases
  • Corporate, Funds, Finance and Disputes work

Historically dominated by the on-island heavyweights, Maples and Walkers, the Cayman legal market now houses offices of every major offshore law firm in the world. While the big two have lost none of their lustre and continue to figure high in all league tables, the field is simply much more crowded now.

Competition comes in the form of the big players from the other major offshore financial centres; Carey Olsen, Mourant, Ogier, Bedell Cristin and Collas Crill (all historically rooted in the Channel Islands), Appleby and Conyers (both originating out of Bermuda), and Harneys (the long-time market leader in BVI). Add in a fast-growing local stand-out in Campbells, and respected boutiques such as Travers Thorp Alberga and Stuarts, and the options are as strong as they have ever been. Onshore firms have only a very limited presence, most notably in the form of Kobre & Kim, a US/international litigation outfit which has a good reputation in high-value Cayman disputes.

Corporate and Finance work is the mainstay of the Cayman law firm, whether it be transactional matters or litigation. All firms have expertise in the funds sector and the leading practices field funds teams that compare favourably to most teams in the onshore world, both in size and quality. As the Cayman financial economy begins to diversify, corporate roles are also emerging in sectors such as insurance and notably cryptocurrency/fintech. Private client teams focus heavily on trusts and private wealth for an ultra-high-net-worth client base, making for interesting work if this is your specialism.

The firms maintain efforts to hire and develop locally trained lawyers, but a large majority of positions are still staffed by ex-pats from the leading firms in the UK, Australia, New Zealand, Canada and South Africa.

The Legal Recruitment Market

  • Funds
  • Banking & Finance
  • Corporate
  • Litigation & Insolvency
  • Private Wealth
  • Cryptocurrency/Fintech

Given the nature of the Cayman economy, it should surprise no one that recruitment is dominated by vacancies for lawyers with experience in Corporate, Funds, Banking & Finance, Commercial Litigation & Insolvency, or Trusts. That is not to say this list is exhaustive. In recent months we have handled roles in Financial Services Regulatory, Corporate Insurance, Commercial Property and the increasingly common request for ‘someone with an interest in crypto’.

In common with most markets, peak demand is at three to seven years’ experience, but as teams have matured and movement within the market has soared, demand for more senior hires has risen notably. We now see roles up to and including Partnership, although it is important to stress that prospective candidates at that level are going to need a sought-after skillset like funds, prior offshore experience, or a book of contacts that promises to deliver business.

For work permit purposes you must be qualified in a Commonwealth jurisdiction, with at least three years’ post-qualification experience by the time you start. A strong track record is vital so you will probably come from a large, well-known commercial law firm but lawyers with the right experience and different credentials, perhaps working in-house or with a high-quality boutique, should certainly not rule this out. Private client lawyers will need to have worked in a high-net-worth practice, ideally with some exposure to trusts.

Culturally, the firms tend to look for ‘down to earth’ people with strong communication skills. Team players are highly valued and the ability to build relationships with potential clients over a drink in a local bar or a round of golf is also at a premium.

One final point – they will want to know that you are realistic about what to expect and any sense that you are being seduced by the lifestyle and haven’t thought about the job will set alarm bells ringing, so do your research.

Cayman Island Beach

Being a Lawyer in the Cayman Islands

  • International work
  • Enviable lifestyle
  • No tax
  • Excellent salaries
  • Lucrative bonus schemes

While Cayman is undoubtedly a world apart from city life, the deals, the cases, the stakes are the same. As a Cayman lawyer you will frequently be instructed by major onshore law firms, offering opinions on sometimes very technical aspects of offshore law. The work is entirely international and while New York and London are still the lifeblood of the island, China, India, the Middle East and Latin America are all strong sources of work.

On a day-to-day basis there will of course be some differences. You will be working on Cayman law for starters, and while it is heavily based on English common law there are differences. You may also notice that the volume of matters you advise on increases while the elements of the matter that concern you shrink.

On the plus side, you can expect to spend less time on the heavyweight documentation than you would do onshore, but you will need to be confident juggling multiple demands, and the ability to think on your feet will be priceless. You will also need, at times, to be comfortable taking a more peripheral role on the deal/case rather than


being at the core of it, although for most associates this is offset by the fact that their personal level of responsibility increases.

If work-life balance is a driver in your move it is important to recognise that people still work hard here. In the leading firms at least, you shouldn’t bank on hitting the beach at 5pm every night. That said, very few Cayman lawyers have any complaints on this front. While most will put in the hours sometimes, there is no culture of expectation around regular late nights or weekends. Factor in that your journey home could be a ten-minute stroll along the harbour or drive along the coast and you can see why for many, this is about as good as work-life balance gets in the upper levels of the legal profession.

Salaries vary but the top firms pay very well and even those moving from a well-paid onshore role will almost certainly gain financially when you consider that there is no direct taxation. Several firms also have lucrative bonus schemes that allow those who perform well to enhance their earnings. One word of caution, the cost of living is high as all goods are imported so that will offset some of your tax-gain, but in general, this should be a good move for you financially.

“There are excellent professional opportunities on the island”


Assuming that you meet the criteria set out above, gaining admission in the Cayman Islands should be straightforward and happens soon after your arrival on the island. One point of note for litigators, it is a fused profession so Caymanian admission allows you to stand in court.


Work permits are required for all non-Caymanian citizens and are typically allocated on a two-year basis. In order to secure a work permit you will need to be eligible for admission in Cayman (see criteria above) and the firm will need to have satisfied the authorities that they have been unable to source an appropriate candidate locally. For most, the permit process tends to be quite straight-forward, but it can take eight to ten weeks and you should remember before resigning that it is possible – if extremely unlikely – that it could be declined. Spouses are entitled to live on the island and can apply for a work permit. Unmarried partners accompanying a lawyer would need to apply independently.


Cayman has a plentiful supply of apartments and condominiums, and many lawyers will live in modern blocks with sea views, tennis courts and swimming pools. Popular locations are Seven Mile Beach and George Town as both will put you within very easy reach of the office. Prices vary depending on the location and can fluctuate according to market demand. For an overview of the current rates, get in touch and we will point you in the right direction. Whilst few people buy property on arrival, many lawyers have subsequently put down roots on the island and there are no limitations on foreigners acquiring property.


Cayman education is widely considered to be excellent at primary and middle school levels. Opinions differ on the standard of secondary education with some finding it perfectly acceptable whilst others decide to either relocate away at that point or send their children to boarding schools in their home country or North America – it really depends on individual preferences.

The Career Path

People sometimes ask if a move offshore will damage their career. It won’t. Experience gained in a top Cayman firm is highly regarded, whether in London or other global cities, in another offshore market or even in-house. The nature of Cayman work is such that you will inevitably get extensive exposure to investment funds or financial services clients, a sector which remains in the highest demand internationally.

Of course, it does take you in a certain direction and if you return onshore you will need to rebuild your practice before being able to push for Partnership, but it certainly doesn’t close the door. If you want to move back onshore there is no reason to think that you won’t return to a top firm.

For many offshore lawyers though, they never contemplate going back, preferring to remain offshore, either aiming for Partnership in Cayman, every bit as realistic but challenging as onshore, or moving to one of the other centres where the offshore firms proliferate. The Channel Islands, BVI, Bermuda, Hong Kong, Singapore, Dubai, Dublin, all are potential next steps for a Cayman lawyer, as is the London office of an offshore firm.

Cayman Islands water view

The international team at Origin Legal has been helping lawyers to make life changing moves to the Cayman Islands since 2001. We aim to simplify what is a potentially complex move, employing our vast experience to advise on every stage from initial fact finding through to starting at your new firm.


To find out more about opportunities in the Cayman Islands, discuss your options offshore or to register an interest, please contact us on:

Jason Horobin

+44 (0)1206 233514 / +44 (0)7712 051941

[email protected]

Connect with me on LinkedIn

Charlotte Hooper

+44 (0)1206 233515

[email protected]

Connect with me on LinkedIn

All approaches are treated in the utmost confidence and no details are ever released to any of our clients without your advance approval. You can view more resources via the international section on our website www.originlegal.co.uk


I can't recommend Jason highly enough. He's responsive, patient, measured, and always knows the right thing to say. I'm also grateful to him for staying involved the entire way through the process, which, due to Covid, was drawn out over 12 months (from interview to arrival on Grand Cayman). He stuck with me the whole way through, and I felt more confident having him to lean on and bounce things off. I have no hesitation recommending him to anyone. (Associate, Carey Olsen, Cayman Islands)

Jason really is outstanding. He helped place me in the perfect firm for me; his reading of the firm's culture and fit was second to none. His in depth and hands on knowledge of the offshore legal world was a welcome support and he was responsive and engaging throughout - no question was too small (or daft!). He made the move offshore a genuine pleasure and helped manage a really smooth transition and process, from initially being put forward for the role to starting. I will be recommending Jason to anyone considering a move offshore - he's the "go to" in my eyes. (Associate, Mourant, Cayman Islands)

Jason is by far the best recruiter I have ever worked with and his key strength is that he is genuinely open and honest with candidates. I've worked with recruiters before who I felt were willing to push me into roles that weren't suited to me and Jason stood out because I trusted his advice completely. Thanks to Jason I was able to secure a great position in the Cayman Islands and I haven't looked back since! (Associate and now Senior Counsel, Walkers, Cayman Islands)