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Getting to the Cayman Islands

2 April 2012


One of the reasons I started this blog was to record some of the experiences from our time between jobs.  I have worked as a lawyer in London for over six years, my girlfriend Anna doing the same, and we decided that we wanted to work abroad.  Being a UK lawyer is quite a fortunate position as (a) English law is often used in contracts worldwide; and (b) English common law is the basis of law in many Commonwealth/ex-Commonwealth countries.  This means that our training is transferable and we can work in various jurisdictions with various degrees of retraining.

When we quit our jobs, we were trying to decide between the Cayman Islands (always a high priority of mine), the British Virgin Islands (better than the Cayman for sailing but less developed and with slightly different work), Hong Kong or Dubai (very unlikely, but we had a friend there that we were visiting, lawyers are in demand and we had no current job offer).  Although we have worked with a lot of Australians and think the lifestyle there would be great, we decided against Australia as it was simply too far away and we didn’t want to spend all our holidays coming back for weddings and seeing friends and family (weddings were already heavily dictating our travel plans having 3 various wedding commitments during our time away).

Fortunately, after a great 2.5 months in Africa, we secured jobs in the Cayman, making the last three months more definite and meaning we could splash out a little more than originally anticipated.  It is now only a few weeks until we get to the Cayman and I am (a) getting quite excited about the diving; and (b) getting quite nervous about getting back to work.  Although it had always been my dream to work in the Caribbean so it was really a no brainer for me, people are starting to ask some questions about our move that suggests I should do a little research, so here we go… (although this is admittedly going to be mostly things that I am interested in and will be updated, if you have anything useful to contribute, please do add a comment below or drop me an email!).

About the Cayman

The earliest reference I recall to the Cayman came in the film of the John Grisham book “the Firm” (where Gene Hackman’s character and various other lawyers snuff it…).  Despite such inauspicious beginnings, it seems a productive place to practise as a lawyer.  Due to its tax free status (rumoured to have been granted by George III (of England) following an act of bravery rescuing British sailors but more likely to be a prosaic business solution) the Cayman Islands have grown into one of the largest offshore financial centres in the world and featured heavily in a lot of litigation following the recent global financial crisis.

Although the Cayman is currently a financial centre with appropriate regulation, it has had its share of piratical visitors and there are a number of wrecks to explore in the surrounding waters.

Where is the Cayman?

The Cayman Islands are in the Western Caribbean, part of the Greater Antilles, around 100 miles South of Cuba and 100 miles to the West of Jamaica.  The Cayman Islands actually consists of three islands – 1) Grand Cayman (where most of the financial services are based), 2) Cayman Brac and 3) little Cayman. I’ll keep it at that for now…

Best time to visit

It seems difficult to get a consensus on this as the Cayman has a tropical marine climate with a wet season (May to October) and a dry season (November to April).  The average temperature fluctuates from about 25 degrees celcius in January to 29/30 degrees in July and August when it is apparently very humid.  The Cayman experience hurricanes and the hurricane season is June to November and the Cayman apparently experiences the effects of a hurricane on average every other year.  Whilst this may well be quite an experience, I’m hoping they will hold off for a few years.

I’ve been told that March/April is the optimal time to visit the Cayman Islands but will confirm that in due course…

Things (I would like) to do in the Cayman

Other than, naturally, working hard at my career and providing an excellent legal service to my firm’s clients, the following are some things I would like to explore in my free time:

  • Work on my underwater photography and diving generally – including buying a decent underwater camera;
  • Work out which dive sites are best for my visiting buddies;
  • Visit stingray city – a place that developed from fishermen dumping offal that attracted rays and now provides a tourist attraction that includes swimming, standing and diving with rays;
  • Pirate week – this looks like a great laugh and not only includes themed parties but a 5k and 10k run, a 5k ocean swim, a lion fish culling competition and plenty of drinking opportunities
  • Cayman triathlon – I’m hoping the climate will be perfect for regular training and the maximum 10m climb in the Cayman should prevent my nemesis of hill climbs;
  • Cayman marathon – after a disappointing time in Paris I’m hoping to get a pb on what must be a nice flat course confirmed by this write-up;
  • Round the island race – having done the Isle of Wight Round the Island Race last year and signed up again for this year, I am keen to get involved in the Cayman Round the Island Race and other sailing in Cayman;
  • Get some PADI diving specialities under my belt – maybe Lionfish hunting, deepdiving, wreckdiving and nightdive (after my disastrous experience in Cambodia);
  • Beach volleyball – should be a simple aspiration but growing up in Dudley I didn’t have much chance to train for this although I am always happy to make up team numbers;
  • Live on a beach – when will I ever get the chance again if I come back to the UK?

Places I am hoping to go from the Cayman

The Cayman has a few direct links but many flights go via Miami

  • Cuba;
  • New York and Washington DC – I wasn’t overwhelmed by New York the first time and want to give it another chance, but I did like Washington and would love to go back for another long weekend;
  • The Southern States of the US;
  • Jamaica;
  • Mexico;
  • The rest of the Caribbean;
  • Honduras;
  • Ecuador;
  • Skiing in US/Canada, a long distance from the UK but ideal for the Cayman;
  • Galapagos Islands – apparently only six hours flight;
  • The US national parks – we originally wanted to do this as part of our time out but most would have been closed due to snow/ice;

Useful sources of information

If you have any tips for the Cayman or that part of the world, please let me know, otherwise I will write up some more targets as I get to know the area!

I'm ready to dive in...

  1. Moving to the Cayman Islands?! SUPER JEALOUS! I can’t wait to see your underwater photography pictures- I couldn’t think of a more appropriate place to enhance your skills 🙂

    I’m getting the itch to work abroad next year actually.. I should look into moving to somewhere in the Caribbean as well 😀


    • Thanks, I would recommend that you take the leap and do it, so many people have told us they wanted to but never got around to it. Good luck!

  2. I’m planning on visiting the Cayman Islands either this year or next and found your article really helpful – so jealous that you’re going to live there!!

    • Will hopefully write some more when I get there and give you the full low down! Cheers, I’m sure where you live has its good points!

  3. Jez, you and Anna should love Cayman. Lots of work for legal folk particularly in the hedge fund space. You will find the pace much slower than London.

    The climate is great and the beaches & diving amazing. Lots of expats in Cayman so you will be in good company.


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