Welcome to Jerry & Sheila Island Living 🌴
I traded the U.S. grind for purpose, peace, and real estate in the Dominican Republic. After 21 years of service, I’ve shifted from the "rat race" to building a legacy. We provide the blueprint for your lifestyle redesign.
From navigating DR residency to managing profitable Airbnbs and growing a bilingual family, we share the unfiltered truth so you can move with confidence.
🚀 WHAT WE COVER:
Expat Relocation: Logistics, residency, and cost of living.
Real Estate & Investing: Turning a pension into wealth through DR property.
Bilingual Life: The raw reality of cross-cultural marriage.
Island Reset: The "Peace over Pressure" mindset.
📲 CONNECT WITH US:
🌐 Website: www.jerrysheilaislandliving.com (Guides & Consultations)
📸 Instagram: @jerrysheilaislandliving
📘 Facebook: @jerrysheila2023
New videos weekly. Subscribe to join the Island Crew.
#jerrysheilaislandliving #dominicanrepublic #expatlife #realestate #financialfreedom
Jerry & Sheila Island Living
🎥 Watch here:
https://youtu.be/NIIk8HHKBO4
🇩🇴 Is Expat Life in the Dominican Republic Still Worth It in 2026?
Everybody talks about how affordable the DR is…
But gas prices are up.
Groceries cost more.
Housing isn’t as cheap as it used to be.
And eating out definitely costs more than it did a few years ago.
So here’s the question:
👉 Knowing what you know today, would you still choose the Dominican Republic?
Sheila and I share our honest thoughts in our newest video.
👇 Let us know in the comments:
Would you still move to, retire in, or live in the Dominican Republic in 2026?
1 hour ago | [YT] | 7
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Jerry & Sheila Island Living
🇩🇴 If You Could Live Anywhere in the Dominican Republic, Where Would It Be?
👇 Vote below and tell us why!
Question for the comments:
What part of the Dominican Republic would you choose to live in full-time and why? 🇩🇴
#DominicanRepublic #LivingInDR #MoveToDR #ExpatLife #RetireInDR #IslandLiving #JerryAndSheilaIslandLiving
9 hours ago | [YT] | 3
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Jerry & Sheila Island Living
The Dominican Republic is getting more expensive. Would you still choose to live there?
15 hours ago | [YT] | 2
View 1 reply
Jerry & Sheila Island Living
🎥 Watch here: https://youtu.be/NIIk8HHKBO4
The Dominican Republic is getting more expensive... but would we still choose it?
Gas prices are up. Groceries are up. Housing is up. Restaurant prices are up.
So why are we still here?
In this video, we have an honest conversation about rising costs in the Dominican Republic and the reasons we'd still choose this life despite the higher prices.
👇 Let us know in the comments:
Would you still move to, retire in, or live in the Dominican Republic today? Why or why not?
#DominicanRepublic #ExpatLife #CostOfLiving #RetireInDR #LivingInDR #JerryAndSheilaIslandLiving
15 hours ago | [YT] | 11
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Jerry & Sheila Island Living
🇩🇴 Who is the Dominican Republic MOST attractive to today?
3 days ago | [YT] | 6
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Jerry & Sheila Island Living
Some people dream about slowing down… others actually do it. ☀️🇩🇴
Life isn’t always perfect, but taking time to enjoy the little moments makes a big difference.
What’s the FIRST thing you noticed about this photo? 👀👇
#DominicanRepublic #SantoDomingo #IslandLife #JerryAndSheilaIslandLiving #LifeInTheDR #TravelDR #CaribbeanLife #ExpatLife #PeaceOverPressure
3 days ago | [YT] | 50
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Jerry & Sheila Island Living
What makes someone FAIL in the DR the fastest? 🚨
5 days ago | [YT] | 7
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Jerry & Sheila Island Living
The vacation is over.
The excuses are over.
The reset is complete.
Now it’s time to lock back in.
What’s one goal you’re focused on this month?
👇 Drop it in the comments.
#IslandResetMode #GetBackToWork #JerryAndSheilaIslandLiving #Mindset #Motivation #ExpatLife #DominicanRepublic #PurposeOverPerfection
5 days ago | [YT] | 72
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Jerry & Sheila Island Living
If you were choosing between living in the U.S. or moving to the Dominican Republic, what would be your ultimate deciding factor?
6 days ago | [YT] | 5
View 13 replies
Jerry & Sheila Island Living
🔗 Watch the full video here: https://youtu.be/a89v2ZaeuQg
🚨 NEW VIDEO JUST DROPPED! 🚨
Ever since Sheila’s first trip to the United States, we’ve been hit with the exact same question: Will she ever leave the Dominican Republic to live in America?
In this video, we break down her completely unfiltered first impressions—covering everything from U.S. traffic and public etiquette to shopping, cost of living, and how the education systems compare. Her final decision might surprise you.
6 days ago | [YT] | 60
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