Dan Merriam - Nobu Barbuda, Antigua & Barbuda

Introduction: Leaving Canada for a Better Life Abroad

It’s been nearly a decade since I stepped away from a corporate career in sales and business management to focus entirely on real estate investment and entrepreneurship. Since then, I’ve made mistakes, learned more than I ever expected, and rebuilt my life across borders. Today, I live full-time in the Eastern Caribbean and invest across the region.

My journey started in Hamilton, Ontario, where I began buying property in 2011. I didn’t know much about construction or property management at first—but I learned quickly. Over time, my portfolio grew, and I started working remotely, managing operations from abroad while exploring new opportunities internationally.

After visiting over 50 countries and running the numbers, I realized that living and investing in the Caribbean wasn’t just a dream—it was a logical next move. And for someone who wanted more control over their time, money, and tax obligations, it became the best decision I ever made.

How I Built My Real Estate Portfolio in Canada

In 2011, I bought my first investment property in downtown Hamilton, back when the city was still considered rough, undervalued, and full of opportunity. At the time, I didn’t have a construction background or much investment experience. I was figuring it out on the fly—reading books, knocking on doors, managing tenants, and learning everything the hard way.

Over the next few years, I scaled that one property into a portfolio worth over $15 million by 2020, all in the Hamilton area. I handled everything myself—property management, leasing, capital improvements, financing structures. I was obsessed with the business.

The returns were strong. I was generating 43%+ leveraged IRR on my projects, and I had built the kind of portfolio most investors dream about. But even as the numbers looked good on paper, I started to feel like I had outgrown the local market. Cash flow was getting tighter. Government regulations were increasing. And the lifestyle wasn’t matching the freedom I was after.

The Wins, the Losses, and the Hard Lessons

Here’s a full breakdown of what those early years taught me:

I left a stable career in 2014 to go all-in on real estate—a decision that terrified me but turned out to be the best call I’ve ever made.
By 2020, I had built and managed a $15M+ portfolio entirely on my own—boots on the ground, fully active.
During the pandemic, I worked remotely while traveling across 20+ countries. It was the first time I realized I could run a real estate business from anywhere.
I launched and failed a property technology startup called ICAREUM in 2020–2021. It didn’t work, and it cost me a lot—but the experience was invaluable.
In 2021 and early 2022, I strategically exited 90% of my Canadian real estate portfolio, capitalizing on market strength and shifting focus internationally.
I helped launch Essential Real Estate Partners, a Canadian real estate private equity fund with top-tier operators.
And in 2021, I began actively investing in the Eastern Caribbean, starting with Antigua and Barbuda.

It wasn’t a straight path. But each move brought me closer to where I needed to be.

The Pivot: When I Started Looking for a Life Outside of Canada

My perspective started to shift during my time living in Guangzhou, China in 2019 and early 2020. I was doing consulting work, working with clients remotely, and getting exposed to international markets in a deeper way.

Around the same time, I started looking into non-residency strategies. I was researching long-term visa programs like Malaysia’s MM2H (Malaysia My Second Home) and Thailand’s Elite Visa. I was running spreadsheets comparing effective tax rates, cost of living, and quality of life across multiple jurisdictions.

Meanwhile, Canadian property values were surging, and the equity in my portfolio was rising quickly—but so were my taxes. I started to realize that being tied to one country didn’t make sense anymore. I had options. And more importantly, I wanted to build a life that wasn’t centered on the CRA.

In 2021, after months of planning and conversations with advisors, I left Canada and established tax residency abroad.

My Office in Hamilton, ON Overlooking West Harbour Marina

Why I Chose Antigua and Barbuda

I didn’t just randomly choose Antigua. I ran a deep analysis across dozens of countries. I looked at tax policy, cost of living, real estate laws, language, quality of infrastructure, access to banking, and long-term investment upside.

Panama had potential. So did Uruguay, Portugal, and Belize. But I kept coming back to the Caribbean, and Antigua in particular.

Here’s why Antigua made sense:

It’s English-speaking, with strong rule of law and a common-law legal system.
It has a respected Citizenship by Investment (CBI) program, offering second passports and strong visa-free access.
The island is peaceful, welcoming, and open to foreign investment.
It offers real estate value upside and lifestyle quality that felt right to me.
And from a non-resident tax strategy, Antigua aligned perfectly.

I’d read Don Campbell’s book Real Estate Investing in Canada over a decade earlier. He talked about finding your “personal Belize”—that one place that feels like home. For me, Antigua was it.

Leaving Canada Wasn’t Easy—But It Was Necessary

I won’t pretend this was a simple or painless decision.

I sold my dream home. I gave away or sold nearly everything I owned. I left friends, family, and a city that had shaped my life. And I did it in the middle of a global pandemic.

Some people thought I was reckless. Others thought I was running away. But I wasn’t.

I was running toward something that made more sense: a simpler, freer, more focused life where I could invest, grow, and live on my own terms.

Waking Up in Jolly Harbour, Antigua and Barbuda

What Life Looks Like in the Caribbean

Today I live in Jolly Harbour, Antigua, and it’s everything I wanted—and more.

My mornings start around 5:00 a.m. I’ll go for a run or hit the beach. The breeze is cool, the water is warm, and the headspace is real. I usually get a few hours of deep work in by 9 a.m.—then meetings, calls, or property visits. I work harder now than I did in Canada—but it’s different. It’s quieter. More intentional.

There are challenges. Things move slower. Banking is frustrating. Real estate deals take longer. Importing anything—from light fixtures to tech gear—is a pain. But once you stop expecting Canada-level efficiency, everything starts to make more sense.

And most importantly: people here value relationships. They care more about who you are than what you do. And once you build trust, doors open.

Becoming a Non-Resident of Canada for Tax Purposes

The tax side of this move was one of the most important—and complex—pieces.

I worked with cross-border tax professionals to properly sever ties to Canada. I canceled health coverage, closed accounts, established new ones offshore, and documented everything. It wasn’t quick, but it was worth it.

I’ve now reduced my effective personal tax rate from over 50% in Ontario to under 1% on most income.

That tax margin doesn’t just impact your bottom line. It frees you up to think long-term, invest more boldly, and live with less financial pressure.

Acquiring Antigua and Barbuda Citizenship by Investment

When I arrived in Antigua, I began the process of acquiring citizenship through the CBI program. It involved a real estate investment, background checks, due diligence, and coordination with government-approved agents.

Now, I’m just weeks away from holding a second passport, which provides:

Visa-free travel to over 150 countries
Permanent access to a jurisdiction I now call home
Greater options for banking, tax planning, and personal mobility

It’s not just about having a Plan B. It’s about building a Plan A that works now—and decades from now..

The Summit at Mount Batur, Bali, Indonesia

Looking Back at the Last 5 Years

As I reflect on everything I’ve been through—from leaving my life in Canada to starting fresh in a part of the world I barely knew—I’ve been asking myself a few questions:

How can I take everything I’ve learned and help guide others through this process?
How do I make it easier, less painful, and more enjoyable for people who are trying to figure out what I just went through?
How do I help others find their own version of “personal Belize”?

I don’t have all the answers. But I’ve spent thousands of hours researching, testing, failing, and figuring it out firsthand. And I know I can help others avoid some of the friction I faced along the way.

Offshore Freedom - Live and Invest in the Caribbean

Helping Others Make the Move

I’m now focused on helping other Canadians and international investors relocate, reduce their taxes, invest abroad, and transition into a lifestyle that’s less stressful and more aligned.

Whether you’re a business owner, investor, or just someone thinking about moving overseas—I’ve probably asked the same questions you’re asking now. And I’ve lived the answers.

Final Thoughts

Leaving Canada wasn’t about running away. It was about building something better. I wanted more time, more clarity, and a lifestyle that didn’t feel like a grind.

The Caribbean isn’t perfect, but it’s real. It’s slow. It’s beautiful. And it’s full of opportunity if you know where to look.

If you’re serious about living differently—whether it’s for tax reasons, lifestyle, or legacy—it’s worth exploring. It’s not easy. But it’s absolutely possible.

**Bio**

**Dan Merriam**
Caribbean Real Estate Investor
**Advisor @ Sotheby’s International Realty**
**Partner @ InvestCARICOM**
Helping high-net-worth investors and global families buy and sell Caribbean real estate, navigate citizenship by investment programs, and implement sophisticated cross-border strategies for tax optimization, residency planning, and long-term asset protection. Dan specializes in real estate-backed second citizenship, offshore lifestyle design, and international relocation, drawing on firsthand investment experience across Canada and the Caribbean.

Schedule a personalized 1-on-1 consultation with Dan Merriam to explore tax-free living, second citizenship, or offshore investment opportunities tailored to your goals. As a representative of Sotheby’s International Realty and partner at InvestCARICOM, Dan brings trusted access, on-the-ground insight, and cross-border expertise to help clients build freedom and wealth across jurisdictions.

Writer in Tax Reduction, International Tax Planning, Travel, Citizenship by Investment, Second Residence, Real Estate Investing, Asset Management, Lifestyle Planning, Company Formation, Offshore Banking, Asset Protection, Technology, Entrepreneurship

This article is for informational purposes only; it should not be considered financial, tax planning or legal advice. Consult a financial or investment professional before making any major financial decisions.

Why I Left Canada to Live and Invest in the Caribbean