Navigating High Net Worth Relocation to the Cayman Islands: Expert Insights on Wealth Structuring and Tax Planning

The global landscape of high net worth (HNW) migration continues to evolve, with the Cayman Islands emerging as an increasingly attractive destination for wealthy individuals seeking stability, tax efficiency, and sophisticated wealth management solutions. A recent expert panel discussion brought together international specialists to explore the multifaceted considerations of relocating to this Caribbean financial hub.

The Growing Appeal of Cayman Residency

James O'Brien, a luxury real estate specialist with IRG Cayman who has resided on the island for 18 years, noted a significant uptick in inquiries from diverse international markets. While the United States has traditionally been the primary source of Cayman-bound clients due to proximity—just 75 minutes from Miami—the demographic has expanded considerably. "We're seeing clients from Canada, the UK, Ireland, Monaco, Singapore, Hong Kong, and even Middle Eastern countries," O'Brien explained, highlighting the jurisdiction's broadening global appeal.

The trend reflects broader patterns of wealth migration. As Oliver Ingles, a London-based real estate advisor with DDRE Global, observed, the ultra-high net worth landscape has transformed dramatically over two decades. "Twenty years ago, you could identify six or seven cities where most ultra-high net worth individuals lived. Today, it's literally like a spider's web—people can live and work wherever they want."

Understanding Cayman's Residency Pathways

Cline Glidden, counsel at Ogier in Cayman and former government minister instrumental in developing current immigration policies, outlined the primary residency options designed specifically for high net worth individuals. The jurisdiction offers two main pathways through residency by investment programs.

The first option requires a $1.2 million USD investment in developed real estate and provides a 25-year renewable residency certificate. This pathway was designed with retirees in mind, though there's no age requirement. Residents must spend a minimum of 30 days per year in Cayman to maintain this status.

The second, more substantial option involves a $2.4 million USD real estate investment and offers unlimited residency with a pathway to British Overseas Territory citizenship. This option requires only one day per year of physical presence in Cayman to maintain residency status. However, those pursuing citizenship must demonstrate a permanent connection to the territory by not being absent for more than 90 days per year (excluding business, medical, or educational purposes) over a five-year qualifying period.

"As a British Overseas Territory, the citizenship available through this pathway is actually British citizenship, which is a strong alternative when people are considering options," Glidden emphasized, noting this distinguishes Cayman from Caribbean nations that sell citizenship directly.

The Tax Dimension: US Considerations

For American citizens, the tax implications of relocation are particularly complex. Alicea Castellanos, CEO of Global Taxes LLC and a US international tax specialist, clarified a common misconception: simply moving to Cayman doesn't eliminate US tax obligations.

"Once you are a US person—a citizen or green card holder—you are subject to worldwide taxation no matter where you are," Castellanos explained. Americans relocating to Cayman must continue filing US tax returns and reporting all worldwide income. Since Cayman has no income tax, residents cannot claim foreign tax credits that might be available in other jurisdictions.

The path to actual tax relief requires expatriation—formally renouncing US citizenship or surrendering a green card. However, this triggers the "exit tax" for covered expatriates, which applies to individuals with net worth exceeding $2 million, average annual tax liability above approximately $206,000 in 2025, or those not in compliance with US tax filings for the previous five years.

The exit tax creates a deemed disposition of all assets as if sold the day before expatriation, potentially resulting in substantial capital gains taxation. "It's definitely going to impact their pocket," Castellanos noted, though she emphasized that strategic planning through trusts, foreign corporations, and other structures can help mitigate the burden.

Canadian Tax Planning: A Different Approach

The Canadian tax situation offers both advantages and complexities compared to the US position. Brian Cohen, a private client lawyer with Gowling WLG in Toronto, explained that Canada taxes based on residency rather than citizenship. "Once you've left, you've left. So that's a positive."

However, departure from Canada triggers its own tax event—a deemed disposition of most assets, similar to the US exit tax but without requiring expatriation. Canadian emigrants face capital gains taxation on investments and other assets, though certain holdings like registered retirement plans and real estate receive different treatment.

"The key is making sure you've severed those ties with Canada," Cohen emphasized. "The big three are spouse, dependent, and house." Establishing a genuine departure requires moving family members, selling or transferring the family home, and carefully unwinding club memberships, professional affiliations, and other connections that might suggest continued Canadian residency.

Canadians can obtain deferrals on exit tax by posting security with the government for illiquid assets, providing time to manage the transition more efficiently. Real estate holdings receive automatic deferral until eventual sale.

Real Estate Market Dynamics

The Cayman property market offers diverse options for wealthy relocators, from branded residences like the Ritz-Carlton and Mandarin Oriental to beachfront villas and estate homes. O'Brien noted that luxury properties now command prices exceeding $30 million USD, approaching the valuations of prestigious Bahamas developments.

"You can find a beautiful beachfront condo for $3 million on the famous Seven Mile Beach, or a really nice family home in a gated community," O'Brien explained. Approximately 70% of transactions involve cash purchases, though financing options are available for clients who prefer leverage.

For those maintaining UK property connections, the London market presents particular opportunities. Ingles noted that recent tax policy changes—particularly modifications to non-domicile status—have created a buyer's market. "We've had about 1,000 millionaires leave per month over the past 12 to 16 months," he observed, creating pricing pressure that benefits strategic buyers while requiring careful exit planning for sellers.

Investment Management and Wealth Preservation

Richard Thompson, a wealth manager with EFG Bank in Cayman, emphasized that relocation doesn't necessarily require portfolio restructuring. "As an international private bank, we can offer all currencies and have access to all major security markets. It's not a case of pressing the reset button on any investment strategy."

The key focus shifts to understanding whether clients' objectives have evolved—from wealth accumulation to preservation, from growth to income generation, or toward establishing structures for intergenerational wealth transfer. Cayman's regulatory environment provides access to sophisticated trust structures and other wealth planning vehicles, coordinated with the jurisdiction's favorable tax treatment.

The Importance of Comprehensive Planning

All panelists stressed that successful relocation requires extensive lead time and coordinated professional advice. Cohen recommended clients begin planning at least two years before their intended move, allowing time to address tax attributes, restructure corporate holdings, and ensure clean breaks from home jurisdictions.

"You want to make sure when you go down to the island that your connections to Canada have basically been severed," Cohen advised. "You come down with a clean slate so that as of January 1st, you are no longer Canadian—you are now a Caymanian."

The complexity of international tax rules, substance requirements, and wealth structuring demands a team approach involving tax advisors, immigration lawyers, real estate specialists, and wealth managers working in concert across jurisdictions.

Conclusion

The Cayman Islands continues to strengthen its position as a premier destination for high net worth individuals seeking financial stability, sophisticated wealth management, and quality of life. As O'Brien eloquently summarized: "Residency doesn't really start with a tax form here in Cayman, it starts with a front door. The property here is more than a home—it's an anchor that locks residency and stability for the whole family."

For those considering this significant transition, the message from experts is clear: engage professional advisors early, understand the full spectrum of tax implications, and approach the move with comprehensive planning that addresses immigration, legal structuring, investment management, and lifestyle considerations in an integrated manner.