Moving to Bermuda or the Cayman Islands: What Really Determines If You’ll Settle

Leaving your family and moving abroad is rarely a simple decision. You might want the change, but life has a habit of holding you in place with very real obstacles – schooling, visas, a partner’s job, the comfort of the familiar. All of it is real, and all of it matters.

My own family moved from the UK to Switzerland when I was young, and we stayed for 12 years before returning. I’ve seen both sides of the upheaval. The challenges are obvious, but the upsides are just as real – a broader view of the world, stronger career prospects and opportunities that stay with children for life.

I didn’t expect that experience to end up being so useful in my work. I now help US tax professionals relocate to the Cayman Islands and Bermuda, and I hear the same themes again and again – echoed in conversations with dozens of CPAs and Enrolled Agents every month who’ve already taken the leap.

The ones who settle well tend to notice a few truths early.

Planning ahead matters. Once you’ve identified a role, worked out the visa requirements and signed a contract, the first thing you need is someone who can guide you through the practicalities. That usually means HR, a recruiter and an immigration solicitor. The months before the move are spent gathering documents, attending medicals (yes, still a requirement) and showing up at the embassy on time. It’s all fine if you’re organised, punctual and patient – nothing glamorous, just straightforward admin.

But long before all that, there’s the question of whether the move is actually right for you.

"A good recruiter will push you to explore this properly. In my experience, the important questions aren’t on checklists – they come up at the dinner table. What your partner is really worried about. What your children might gain or lose. How you cope with change. These conversations often decide whether the transition is smooth, stressful or even realistic in the first place."

Then there’s where you’ll live. Cayman and Bermuda are small, but each neighbourhood has its own feel. Some are transient (lots of short-term contracts), others are rooted and family-oriented. Some put you near the beach (most places aren’t far), others make more sense in hurricane season. The best information comes from people already there. Most firms have expats who will happily walk you through the things Google can’t show you.

Schools are another part of the puzzle. If you have children, you’ll need to apply earlier than you think. Places are limited, fees are due and every school handles admissions its own way. Families who settle quickly tend to speak to all the schools, work out what genuinely matters to them and choose based on reality rather than glossy brochures. A scouting trip helps enormously.

Community plays a bigger role than people expect. Those who thrive tend to do three things early:

• They join something – a running club, a church group, a professional body, a swim group.
• They get outdoors more, which in Cayman or Bermuda is almost unavoidable. Most free time ends up being spent near the water or in the sun.
• They mix with locals. Both islands have big expat communities, but only spending time with other newcomers can leave you feeling unanchored. Seek out the people who genuinely love living there and make a point of integrating.

There’s also an adjustment at work. Friendly as the islands are, the professional environments are high-performance. Firms hire internationally because they want people who can deliver from day one. The people who do well treat the first few months like an onboarding sprint – learning the local rules, asking questions early and getting in front of partners and managers rather than waiting to be introduced.

And then there’s lifestyle fit. Cayman and Bermuda reward people who get out and use the place. If your weekends are usually spent indoors, you may find it harder to settle.

"People who’ve stayed long term – some whom I placed years ago – often fall into a rhythm of morning paddleboarding, beach walks, diving courses, barbecues with neighbours and the easy, casual social life that comes with small, international communities. It’s not about reinventing yourself; it’s about using what’s right in front of you."

Finally, it’s worth being honest about the first six months. It won’t be constant sunsets and rum punches. You’ll be learning new systems, meeting new colleagues, figuring out where to buy the things you miss and dealing with the odd spurt of homesickness. Everyone goes through it. The difference between those who stay and those who fly home early is usually expectation. If you understand that the bumpy stretch is temporary, it becomes far easier to manage.

And once you get through it, most people tell me the same thing: their careers have moved faster than they would have at home, their kids are happier and they’ve gained a perspective that only comes from lifting yourself out of the familiar and placing yourself somewhere completely new.

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