Career Spotlight #4: Life and Work in the Cayman Islands - Jacopo's Perspective

Moving to the Caribbean is something quite a lot of us have considered over the years – especially if you work in the US tax field, where you’ve almost certainly seen colleagues make the jump. You get the sunshine and the beaches, yes, but you also land in a place that’s energetic, welcoming and built around a global financial community that’s far bigger than the island itself.

I helped Jacopo Di Giovanni make the move to Cayman 4 years ago, and he’s still there today - now working as a Senior Tax Manager. Catching up with him recently felt like a great chance to hear how the experience has unfolded and why the island has kept him there.

When I started by recalling our first conversation, back when I first presented him with the option of moving to Grand Cayman, he put it plainly:

What drew you to the Cayman Islands, and what tipped the balance?

“The Cayman Islands offered strong career prospects in a global financial center, combined with an appealing lifestyle and safe, vibrant community. The balance tipped when I saw the opportunity for both professional growth and personal well-being.”

The attraction wasn’t just the scenery. For many, the professional upside is just as compelling as the lifestyle shift - a combination that’s harder to find than people imagine.

What aspects of life in Cayman do you enjoy most?

“I enjoy the sense of community, outdoor lifestyle, and easy access to beaches and amenities. The friendly, multicultural environment and work-life balance are standout features.”

Biggest surprise about living and working there?

“Positively, I was surprised by the professionalism and welcoming atmosphere. The main challenge was adjusting to the high cost of living and the realities of island life.”

That balance between high standards and genuine warmth is something Cayman regularly surprises people with. And while the cost of living is a factor, the 0% income tax, lifestyle, and career opportunities tend to outweigh it.

How does the working culture compare?

“Cayman’s work culture is international, collaborative, and less hierarchical. There’s a strong focus on relationships and flexibility, with a healthy respect for work-life balance.”

Day-to-day benefits, professionally and personally?

“Professionally: exposure to global clients, rapid skill development, and broader responsibilities. Personally: short commutes, outdoor activities and a supportive community.”

Sailing, scuba diving, swimming, hiking - you name it. If you like outdoor sports, Cayman is a fantastic place to be. The island gives you back hours of your life compared to most major cities, and people use that time well.

Challenges in the first year and how you overcame them?

“Initial challenges included adapting to the climate, logistics, and building networks. I overcame these by engaging with the community and seeking mentorship.”

I’ve written about this with others who’ve made the move (here). The people who succeed are those who manage their expectations during the first six months and make a real effort to integrate into the local community, embracing island living rather than recreating the life they left behind.

How has Cayman shaped your career?

“Cayman broadened my expertise and expanded my professional network through international exposure.”

This is the bit that often gets underestimated. Cayman’s scale means you mix with people and clients you might never get near in larger cities. There’s a huge amount condensed into a small place, and that intensity accelerates your development.

Common misconceptions about moving to Cayman?

“People often think island life is slow or lacks challenge, or that integration is hard. In reality, the business environment is dynamic and the community is welcoming.”

Cayman is a financial services hub - one of the biggest and most centralised in the world. There are plenty of misconceptions about living in the Caribbean, and the pace and complexity of the business environment shouldn’t be underestimated.

Key advice for someone considering relocation?

“Research thoroughly, set realistic expectations, and connect with current residents. Flexibility and openness are essential for a successful transition.”

I can attest to the importance of staying flexible. Moving abroad isn’t easy. I've done it before, and there are a lot of moving parts to line up, from schooling to a partner’s job to rental contracts. For those who can make it work, the result is an incredibly exciting, family-friendly life that you might never have imagined was possible.

Thank you, Jacopo, for the insight – and it's great to catch up after all these years.