Our Island
Journey
From two different worlds to one shared purpose — inspiring expats to live, love, and grow in the Dominican Republic.
Peace Over Pressure. Purpose Over Perfection.
That is not just our motto. It is how we live.
We communicate across a language bridge that requires 100% focus. If we can build a stable life and a business without sharing a native tongue, we can show you how to navigate any cultural barrier in the DR.
From military life to island life, we have learned that starting over is not about escaping. It is about evolving. We share what most people never show you, which includes the real stories, hard lessons, and laughter behind expat life in the Caribbean.
Bridging Two Worlds We provide the truth from both sides of the island.
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Sheila brings the Dominican heart, cultural expertise, and everyday wisdom.
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Jerry brings the expat mindset, US Army structure, and the strategic execution of a lifestyle relocation.
Together, we show you what happens when love, faith, and purpose meet palm trees and power outages.
How We Help You Through our videos, guides, and consultations, we help you:
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Build your dream life abroad with confidence.
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Understand Dominican culture from the inside out.
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Redefine what peace and success mean for you.
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We expose the expensive myths of island life so you don't waste your pension on mistakes we’ve already identified and cleared.
If you are serious about doing this the right way, book a consultation to get clear guidance based on real experience rather than assumptions.
Welcome to the movement that is bigger than travel. Welcome to Island Living with Jerry & Sheila.
Jerry & Sheila Island Living
After 21 years in uniform, I traded combat boots for flip-flops, and started a new mission: building peace, purpose, and family life in the Dominican Republic.
This journey isn’t just about me, it’s about helping others create their own island reset. Most people come to the Dominican Republic to escape reality. I came here to master it. In 4 years, we’ve built a Top 5% life by applying military-grade discipline to a culture that most foreigners find chaotic. We don't offer 'travel tips'; we offer a strategic roadmap for men who are tired of being broke in the USA and ready to deploy their resources where they actually have leverage.