Cayman Islands VS Bermuda

February 11, 2026

A Career Perspective for Actuaries & Accountants in Reinsurance & Captive Insurance

Introduction:

If you’re an accounting or actuarial professional contemplating a move to the Caribbean’s premier insurance hubs, the decision between Bermuda and the Cayman Islands is a big one. Both territories offer thriving financial services environments, international exposure, and a high standard of living, but there are important differences beyond just beaches and sunshine.

The following explores how these two markets compare from the insurance landscape to cost of living, lifestyle, climate risk, and more.

1. Market Overview: Established vs. Emerging Growth

Bermuda – The Established Giant

Bermuda has historically been the undisputed leader in the global reinsurance market, known for its deep, sophisticated ecosystem of reinsurers, captives, sidecars, and risk-transfer capital structures. The island’s market is robust with a long legacy of actuarial innovation and a high concentration of international players, especially in Reinsurance and Insurance Linked Securities.

Cayman Islands – Rapid Growth & Momentum

The Cayman Islands, while smaller historically, have been growing aggressively as a domicile for captives and specialty reinsurance vehicles. Recent licensing data shows strong expansion in Class B, C and D insurer registrations, with the jurisdiction hitting record highs in new licences and assets under management, a sign of momentum in both captive formation and broader insurance business.

Many firms with operations in Bermuda are now exploring Cayman as a complement or alternative, sometimes to take advantage of nimble regulations, competitive positioning, or operational flexibility.

For professionals, this means more opportunities in Cayman, especially in advisory, actuarial pricing, reserving, and reporting roles alongside the traditional strongholds in Bermuda.

2. Cost of Living & Accommodation

Living in either Bermuda or the Cayman Islands is expensive compared to most places, but there are notable differences:

General Cost Comparison

  • Overall, Bermuda tends to be more expensive than Cayman across many categories such as restaurants, groceries, housing and transportation.
  • Some indices show Cayman’s cost of living is roughly 10-20% lower than Bermuda when accounting for rent and everyday expenses.

Accommodation

  • Bermuda: Highly limited land and rental inventory push prices up; central areas see some of the highest rents globally.
  • Cayman: The rental options are more competitive and easier to secure. There is also no restriction on foreign ownership for residential property, no annual property taxes and no capital gain taxes.

Groceries & Daily Costs

  • Groceries and dining out trend higher on average in Bermuda, while Cayman tends to offer slightly better pricing , though both are high due to import costs.

3. Transportation & Vehicle Ownership

  • In Bermuda, there are local rules that generally mean most residents own only one car, and importation of additional private vehicles is restricted.
  • In the Cayman Islands, owning two cars is far more typical and far less restricted offering families flexibility.

This impacts daily commuting, family logistics, and overall transportation costs.

4. Proximity & Travel Connections

Bermuda

  • Bermuda enjoys excellent connectivity to the U.S. East Coast (e.g., direct flights to New York, Boston, Washington) – a huge plus for client travel, business meetings, and weekend escapes.
  • European connections are also solid, with seasonal services to the UK.

Cayman Islands

  • The Cayman Islands have good links to major hubs in the U.S. and Canada, with frequent flights to hubs like Miami and Dallas. This makes travel to North American and Caribbean destinations relatively easy.
  • European connections are also solid, with seasonal services to the UK.

Both islands are well positioned for international travel — invaluable for reinsurance professionals attending global conferences, client visits or professional exams.

5. Career Trajectory & Professional Environment

Bermuda

  • Established incumbents in reinsurance, captives and actuarial consulting.
  • Deep pools of senior talent, with ample opportunities for specialization.

Cayman Islands

  • Rapidly expanding market with growing demand for actuarial and accounting expertise.
  • Often perceived as more dynamic or entrepreneurial with room to grow into emerging areas like alternative risk and fintech collaborations.

Salary structures vary but are generally competitive in both jurisdictions, though some cost-of-living adjustments may be reflected in offers.

Final Thoughts for Accountants & Actuaries

Both Bermuda and the Cayman Islands offer world-class gateways into reinsurance and captive insurance. Your choice may come down to career priorities vs. lifestyle preferences:

  • Choose Bermuda if you want the prestige and scale of a long-established global insurance community with elite actuarial and accounting talent around you.
  • Opt for the Cayman Islands if you’re excited about being part of a growing hub, with dynamic career prospects and slightly more flexibility in everyday life and housing.

Either way, working in these jurisdictions is an adventure; professional, personal, and scenic.

If you want to learn more about opportunities in either jurisdictions please contact me on diarmuid@theagnecy.ky