Life as an Expat in Anguilla: What to Expect When You Live in Paradise

Anguilla isn’t just a stunning vacation destination—it’s also home to a growing number of expatriates who’ve chosen the island for its beauty, tranquility, and lifestyle. Whether you’re considering retiring here, moving for work, or investing in property under Anguilla’s Residency by Investment program, life as an expat on this British Overseas Territory offers a unique blend of modern comfort and laid-back island charm.

Trophy Properties Caribbean Real Estate Broker, Lisa DeLong, shares some insights based on her firsthand experience as an expat of the UK owning real estate in Anguilla with her husband Scott and raising their two small children on island.

1. Community: Small, Safe, and Welcoming

Anguilla has a population of about 15,000, and its expat community is tight-knit, friendly, and diverse. You’ll find residents from the U.S., Canada, the UK, Europe, and other parts of the Caribbean. English is the official language, and the island’s low crime rate and respectful culture make it especially appealing for families and retirees.

Locals are known for their warmth and hospitality, and it doesn’t take long to feel part of the community—especially if you participate in local events, join fitness or wellness groups, or support one of the many charitable initiatives on the island.

2. Cost of Living: Island Life, Island Prices

While Anguilla offers tax advantages (no income, capital gains or inheritance tax and minimal property tax), the cost of living can be higher than in major cities due to the import of goods. Groceries, household items, and fuel are typically more expensive than in the U.S. or Europe.

That said, many expats find the quality of life offsets the higher price tags. If you own your property and live modestly, the island can be quite manageable—and luxurious if desired.

3. Healthcare and Education

Anguilla has modern healthcare facilities with local clinics, pharmacies, and a hospital. For major procedures or emergencies, some residents fly to nearby islands such as St. Martin, Puerto Rico or the U.S.

Families with children often opt for the private international school (Omololu International School) offering an IB program. High school students may attend CIA international school in St. Maarten daily by boat.

4. Connectivity and Infrastructure

• Internet: High-speed fiber-optic internet is available, making remote work and digital business feasible.
• Transport: Driving is on the left, and most residents have a vehicle. The roads are well-maintained, and the pace of traffic is relaxed.
• Travel Access: You can reach Anguilla via direct flights from the U.S. (via MIA, BOS or BWI), or fly into Sint Maarten (SXM) and take a short ferry or small flight over.

5. Lifestyle: Beaches, Dining, and Balance

Life here moves at an unhurried pace. Expats often spend their days paddleboarding, reading on the beach, dining in world-class restaurants (Jacala, Blanchards, Veya), or enjoying spa days and outdoor fitness classes.

If you’re coming from a fast-paced urban environment, the adjustment can feel dramatic—but in the best way. No casinos, motorized jet skis or large cruise ships keep the island tranquil. The luxury is in the space, the quiet, and the quality of life.

6. Real Estate & Residency

Owning property is one of the most straightforward paths to living in Anguilla long-term. Through the Residency by Investment program, you can gain permanent residency with a real estate purchase of $750,000 or more (plus fees). This option may be attractive to digital nomads, retirees, and business owners.

7. Things to Consider

• Island Time is Real: Patience is a virtue. Some services (especially during off-season) may move slower than you’re used to.
• Limited Retail Options: While local shops provide essentials, you may still need to shop online or off-island for specialty goods.
• Hurricane Season: From June to November, residents prepare for tropical storms and potential hurricanes. Homes are built to withstand them, but planning ahead is key.

Final Thoughts

Living in Anguilla as an expat offers a slower, more intentional lifestyle in one of the Caribbean’s most pristine settings. It’s ideal for those seeking simplicity, natural beauty, safety, and a close-knit community—with the option to dip back into the wider world when needed, thanks to boat and air transfers to international gateway St. Martin/St. Maarten where you can fly direct to major cities around the world, direct flights to Miami, Boston and Baltimore in the United States and regional flights to Antigua, St. Barth's, St. Thomas and Puerto Rico.

If you’re ready to trade city stress for soft sand and sea breezes, Anguilla might just be your perfect next chapter.

Get Started...

Interested in making the move? Contact us to learn more about available properties, the residency process, and how to make Anguilla your new home. Our Trophy Properties Caribbean team has successfully navigated this transition to ownership for our clients and for members of our team ourselves. We're ready to share our real life advice and tips and with you.