Retiring Abroad on Social Security: Is It Possible? Our Real Numbers Say Yes

Is the American Dream more affordable in Europe? 5 years ago, we left the Chicago suburbs for Portugal. We traded a $13,000 property tax bill for €500 and never looked back. In this video, Wolf breaks down our exact 2026 cost of living after five years of living abroad. From Madeira island to Northern Portugal, we’re sharing the real numbers on housing, healthcare, and how we live a "luxury" lifestyle on a budget. If you're looking for financial freedom or wondering if you can retire on Social Security, this is for you. We are Alan, Leslie and Wolf connect with us for a 1 to 1 conversation about moving abroad. Schedule your 1-on-1 "Move Abroad" Meetup www.itllbefunretirement.com/movingabroad1to1meeting 🌍 MOVE ABROAD RESOURCES FREE Newsletter & Meetups: itllbefunretirement.com Find a Home in Portugal: LCL Real Homes We should have done this sooner! Get The Ultimate Moving Abroad Program www.itllbefunretirement.com/movingabroad-1 🎯 How We Help You Move Abroad At It’ll Be Fun, we specialize in making international relocation easy! Whether you're: ✅ Planning a GAP Year ✈️ ✅ Moving to Portugal permanently 🏡 ✅ Exploring a digital nomad lifestyle 💻 We’ve got the resources, connections, and expert guidance to help you every step of the way! 🌐 Join Our Community 📧 FREE NEWSLETTER Get our latest tips, updates, and moving advice! Sign up on our website: ➡ www.itllbefunretirement.com 📅 MONTHLY ONLINE MEETUPS Join our live Q&A sessions and meet other expats! You can sign up via Patreon or on our website. Patreon: www.patreon.com/itllbefun Website: www.itllbefunretirement.com ✨ Our Trusted Partners & Relocation Resources A list of the services and people we trust to make your move smooth and stress-free. 🏠 Housing & Real Estate (Portugal) LCL Real Homes (Claudia Ribeiro) 📧 [email protected] 📞 +351 967 440 896 🛂 Visa & Immigration Assistance Sandra Fernandes Consultancy (Save 10%) 📧 [email protected] | [email protected] EI Migration Agency (Save 10%) 📧 [email protected] | [email protected] 🌐 www.EImigrante.PT 💳 Taxes & Financial Planning Taxes for Expats (20+ Yrs Experience) ➡ www.taxesforexpats.com/ref/277 Bordr (Portuguese Tax Services) ➡ bordr.com/portugal/tax-filing?via=itllbefun Filomena Silva (Portuguese Tax Expert) - This is who we use in PT 📧 [email protected] 📞 +351 965 013 674 💰 Money Transfers & Banking Wise (International Money Transfer) ➡ wise.prf.hn/click/camref:1100lqeJX Spartan FX (Best Exchange Rates) ➡ www.spartanfx.co.uk/fx-partner.php?sfxtrack=madeira 🚗 Transportation & Car Rentals Discover Cars ➡ www.discovercars.com/?a_aid=Itllbefun 📬 US Mail Services Traveling Mailbox (Virtual Mailbox) ➡ travelingmailbox.com/?ref=1351&campaign=It'llBeFun 🔐 VPN for Safe Browsing Abroad - Protect Your Financial Accounts Surfshark VPN (82% Off + 3 Free Months) ➡ https://get.surfshark.net/aff_c?offer... DISCLAIMER: The information provided on this channel is for entertainment and informational purposes only. We are not financial, legal, or immigration professionals. All information is based on our personal experiences and research. Please consult with qualified professionals (attorneys, tax advisors, etc.) for advice tailored to your unique situation. Some links are affiliates, which means we may earn a small commission at no extra cost to you. #MovingAbroad #CostOfLivingPortugal #GapYear #LivingAbroad #MadeiraPortugal #MovingToEurope #NorthernPortugal #VianadoCasteloPortugal #LisbonPortugal #PortoPortugal #France #Italy #Spain #BragaPortugal #algarveportugal 0:00 The $13,000 Tax Record Scratch 1:02 Leaving the U.S. Treadmill 2:15 Portugal House vs. Chicago Suburbs 3:22 The Truth About IMI (Property Tax) 4:10 Renting vs. Buying in Portugal 5:05 Madeira Island vs. Northern Portugal 6:18 Grocery Budget: Fresh Food for €600 7:45 Restaurant Culture & Cataplana 8:30 Heating & Utility Costs in the North 9:15 Driving to Spain in a 1970 VW Bug 10:10 Private Healthcare Costs (The Reality) 10:50 Retiring on Social Security? 11:15 Is Living Abroad Worth It?