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Our Citizenship Journey Ends Here
Father and son in palermo Italy
itllbefunretiremen
Oct 265 min read


U.S. Expat Retirement in Europe: A Looming Tax Storm?
How Much Is too Much to Pay In Taxes? For the millions of Americans retired or retiring across Europe, financial planning has long been a balancing act between local tax laws and the unique demands of the U.S. tax system. Favorable regimes, like Portugal's recently ended Non-Habitual Resident (NHR) program, have offered years of stability and significant savings.
itllbefunretiremen
Sep 126 min read


Buying a House in Portugal with a Mortgage? Our Unfiltered Guide
Dreaming of buying a home in Portugal but need a mortgage? It's a minefield. Sellers want cash and won't wait for bank approvals. We're Alan & Leslie from It'll Be Fun, and we've cracked the code. Our guide gives you the real scoop on how to navigate Portugal's hot market, beat cash buyers, and secure your dream home without losing your mind (or your deposit!). Learn our strategy and get the expert team you need.
itllbefunretiremen
Jul 96 min read


Moving Overseas - Takes More Than You Think
Thinking of moving to Portugal from the U.S.? Don’t wing it. From visa types (like the D7 or Digital Nomad visa) to real income requirements and unexpected costs, we break down what it really takes to start a new life abroad. This isn’t a vacation—it’s a life reset. Get clear, get organized, and do it right the first time. Bonus: use our 30% off code for the Ultimate Moving Abroad Program!
itllbefunretiremen
May 104 min read


What to Expect When Starting a New Life Overseas
Thinking of starting a new life overseas? Discover essential tips on housing, cultural adaptation, finances, work, and building a support network abroad. Whether you're moving to Lisbon, Paris, or Tokyo, this guide helps you navigate challenges, embrace local culture, and thrive in your new environment. Perfect for expats and digital nomads seeking a smooth transition and personal growth.
itllbefunretiremen
Apr 305 min read


America’s Man-Made Crisis:
How Tariff Wars Are Threatening Your Future —
and What You Can Do About It
itllbefunretiremen
Apr 295 min read


Renting in Portugal in 2025: What Americans Really Need to Know (That No One Tells You)
Renting in Portugal in 2025 can be challenging, especially for Americans unfamiliar with the local process. From understanding legal lease requirements to dealing with limited inventory and landlord preferences, this guide explains what to expect, what’s changed, and how to successfully secure a rental for your move abroad. Learn the key differences and how to avoid common mistakes.
itllbefunretiremen
Apr 255 min read


Living Off One Social Security Check: A Smart Approach to Financial Freedom
Facing a Chaotic World Together Let’s be honest: the world feels a little upside-down right now. Tariffs are soaring, countries are...
itllbefunretiremen
Apr 105 min read


Portugal Taxes, NHR 2.0- Everything You Wanted to Know It'll Be Fun
Portugal Taxes - Here's the basics on the new NHR 2.0. See if you qualify for tax savings.
itllbefunretiremen
Feb 74 min read


"Embracing a New Life Abroad: How We Made the Leap"
How we live a better life in Portugal. We left the USA to find adventure, live for less and finally enjoy our lives.
itllbefunretiremen
Sep 2, 20244 min read


YANKEE GO HOME
Portugal Doesn't Want Immigrants At Least Not Always
Leslie
Jul 31, 20244 min read


A Bar, a Garden, and a Leap of Faith Led Us Around the World - Moving Abroad
We moved from Ohio to Chicago and now to Portugal! It's never too late to start a new adventure. Let us show you how to make your dreams com
Leslie
Jul 20, 20243 min read


A World of Opportunity: Our Story of Moving Abroad and Inspiring Change
Bom dia! A decade ago, we dreamt of an adventurous retirement abroad. Now, we're living that in Europe. #It'llBeFun
Leslie
Jun 27, 20246 min read


Navigating the Pitfalls: What Not to Do When Planning to Move Abroad
Moving Abroad What You Need To Know and How To Do It!
itllbefunretiremen
May 8, 20243 min read
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