These days, some people are heading to the islands for more than a vacation. Remote work, retirement or a major lifestyle change grants the freedom to relocate, and new residents are trading traffic and freezing winters for the turquoise waters and white sand beaches of islands like St. Lucia, Antigua and Barbuda and the Dominican Republic. But while island life may seem relaxed, the logistics of moving to an island require more planning than you might think.
Wheaton has decades of experience assisting families with full-service moving, so we understand the emotional and logistical complexity of life-changing moves. If you’ve been thinking about moving to an island, here’s everything you need to know.
The Practical Side of Paradise: Unique Challenges of Island Relocations
Moving to an island is certainly different from traveling there on vacation. In our experience, it requires a different relocation strategy than a mainland move. Thankfully, Wheaton’s expertise in international and remote relocations gives us the upper hand in pinpointing these common obstacles:
- Limited shipping access: Typically, a moving truck can transport your belongings to the new house. In an international move, you need to pay for overseas shipping to get your belongings to their destination. Research applicable shipping methods, including their respective fees and customs requirements.
- Timing and delays: When planning overseas, you need to accommodate others’ schedules and external factors. The weather may cause a delay, shipment dates may be postponed and other logistics might cause interruptions.
- Higher expenses: You’ll also want to keep moving expenses in mind for an island relocation. Transportation may be subject to surge pricing if booked at the last minute, import costs can be expensive and island living can generally be pricier than you’re used to. You’ll also need to consider the cost of residency or a visa.
Legal Logistics: Residency or Citizenship Requirements
To determine the proper documentation for moving to an island in the Caribbean, figure out if you need a residency or citizenship in your new country or island. Unless you’re establishing permanent citizenship, residency permits are a typical requirement for long-term living.
Antigua and Barbuda offer options to move through tax residency programs, temporary residency programs or citizenship through investment. To encourage foreign investment, those who purchase real estate in this region can obtain second citizenship in return for their investment.
St. Kitts and Nevis—as well as St. Lucia—also offer citizenship through investment. By creating this quick path to citizenship, these islands offer great flexibility and eligibility for extended family. There are also visa-free travel opportunities to other countries, tax benefits and quick application processes through this method.
One can obtain residency in the Dominican Republic through a quick application process. Temporary residency is renewable annually and can be transitioned into permanent residency. After two years of permanent residency, holders can apply for naturalisation.
What You Can (and Can’t) Bring With You
Remember that it’ll be much trickier to take your belongings to an island than to another state. After all, everything will need to be documented and shipped, which can be expensive and logistically challenging. Check on import restrictions as far in advance as possible to determine whether you can bring furniture, appliances and vehicles with you. Also, make sure you have a secure storage location for customs paperwork and visa documentation.
You’ll likely need to downsize when moving. Keep essentials and sentimental pieces, or utilize Wheaton’s storage in the United States if you’re not ready to part with certain items permanently. Our top tip for a seamless transition is to work with a trusted and reliable relocation partner who understands customs and local port procedures. With such a high-stakes relocation, it’s better to be safe than sorry.
Cost Considerations: What to Budget For
Island relocations aren’t vacations with a finite budget and a return ticket. Before you move, work on a budget plan that includes your moving expenses, transition costs and the new cost of living. Aside from the general relocation expenses, you’ll also want to think about the logistical fees.
Where are you planning to live? Will you be renting or exploring homeownership (the latter of which will affect citizenship)? What kind of deposits and setup costs will need to be paid before arrival? Should you invest in local moving services or full-service international moving services?
Also, do some research on the prices of groceries, fuel, internet and utilities. Imported goods are often subject to duties and taxes, which can impact your budget. Island economies greatly vary, and you’ll also need to consider any non-monetary lifestyle adjustments.
Settling Into Island Life
Aside from the logistics of moving, island living can be very enjoyable! You’ll have access to all kinds of privileges, from beautiful scenery to idyllic weather to friendly communities. But even so, it may take some time to transition into a new culture and environment, including one that exhibits a slower way of life.
Before making the move, we recommend taking an extended pre-move visit. That way, you’ll be able to observe and study important local etiquette, language barriers or infrastructure challenges. While some deeper factors may not be revealed until well into your residency, a pre-move trip will help you embrace the new lifestyle even before moving day.
Social media and internet research can also help with preparation tips for your new home. Will you need to adjust to the climate? Are children accompanying you internationally? Take some time to look into housing options, nearby amenities and schools, if applicable.

Final Checklist: Is Island Living Right for You?
Not everyone can partake in island living—that’s what vacations are for! But if you have your heart set on moving to an island, start building your relocation checklist:
- Logistical support: Any relocation requires some assistance. Choose a full-service mover that can do more than just transport boxes. Wheaton offers packing, supplies, storage and logistical reinforcements for island moving and beyond.
- Financial preparation: As with any move, financial readiness is key. Will you be obtaining citizenship through investment programs? Are you aware of the required moving expenses and living costs?
- Emotional planning: Relocations are stressful, especially when you’re moving to a remote area like an island. Patience and flexibility are crucial in reducing stress, as is maintaining a sense of adaptability to your new environment.
How Wheaton Helps You Move Your Life Overseas
Whether you’re moving across the country or across the globe, Wheaton’s compassionate, full-service approach to complex moves makes us a reliable relocation partner. We prioritize transparency and trust in every project, ensuring customer care is a priority at every step. When you’re ready to start your move to an island, get a free estimate for a smooth transition to paradise.