The $8 Milk Decision

Is Retiring Abroad Right for You? A Real Talk Guide to Portugal, Panama, Barbados, and Mexico

I'll be honest with you. Back in 2019, if someone had told me I'd be seriously researching retirement outside the U.S., I would've been skeptical. My husband Norman and I had a solid plan: stay put, enjoy our grandkids, maybe take a few nice vacations. But then we started doing the math on our retirement income. And then the pandemic hit and everything changed.

Suddenly we were stuck at home, watching the news, and asking ourselves: is this really where we want to spend our retirement years? When things started opening back up, we began looking at options we'd never seriously considered before.

Maybe you're in a similar spot. Maybe your retirement fund isn't stretching like you thought it would. Or maybe the past few years made you rethink everything about how and where you want to live. Or perhaps you're dealing with health issues and wondering if there's a better way to live well without going broke paying for it.

Whatever brought you here, you're not alone. More Americans over 50 are looking abroad, and for good reason. But here's what most retirement abroad guides won't tell you: it's complicated, it's not for everyone, and you need real information, not just pretty pictures and vague promises.

The Three Big Reasons People Are Looking Elsewhere

Financial Reality Check

Let's start with money because that's what most of us are thinking about. In many U.S. cities, a comfortable retirement now costs $60,000 to $80,000 a year for a couple. That's if nothing major goes wrong health-wise. In places like Lisbon or Panama City, you could live comfortably on $3,000 to $3,500 a month, total. That's $36,000 to $42,000 a year.

The difference isn't just about cheap rent. It's healthcare that doesn't bankrupt you. It's fresh food that doesn't cost a fortune. It's being able to go out to dinner without checking your bank account first.

Political Exhaustion

I'm not going to get into politics here, but I will say this: some of us are tired. Tired of being divided into camps. Tired of feeling like we have to defend our right to exist comfortably. Tired of the constant noise. Moving abroad doesn't solve everything, but it does give you some distance and perspective. Sometimes that's exactly what you need.

Health and Lifestyle

Here's something that surprised me during my research trips: healthcare abroad can be really good. Not "good for the price" but actually excellent. Portugal has modern hospitals with English-speaking doctors who spend time with you. Panama has top-tier medical facilities because of all the international patients. And the lifestyle? Walking more, fresher food, less stress, actual work-life balance (even in retirement). It adds up.

The Four Destinations Worth Considering

Let me break down what I found in each place. These aren't tourist impressions. I spent real time in each city, talked to real expats, and tracked actual costs.

Lisbon, Portugal

The good: Gorgeous city, amazing public transportation, excellent healthcare, walkable neighborhoods. You can get a furnished one-bedroom apartment in a decent neighborhood for €1,200 to €1,600 a month. Healthcare through the public system is practically free, or you can get private insurance for around €50 to €100 monthly.

The reality: It's getting more expensive as more people discover it. English is widely spoken in Lisbon, but you'll need some Portuguese for daily life. The bureaucracy is real and slow. But the quality of life? Hard to beat.

Panama City, Panama

The good: U.S. dollar economy (no exchange rate worries), excellent Pensionado visa program with discounts, modern infrastructure, direct flights to the U.S. You can find decent apartments in safe areas for $1,200 to $1,800 monthly. Good private healthcare at a fraction of U.S. costs.

The reality: It's hot and humid year-round. The city sprawls, so you need to choose your neighborhood carefully. Some areas feel very American (which can be good or bad depending on what you want). Spanish is essential for anything beyond tourist areas.

Barbados, Barbados

The good: English-speaking, Caribbean lifestyle, 12-month visa for remote workers and retirees, familiar grocery options, no major language or cultural shock.

The reality: Remember that $8 milk I mentioned? Barbados is expensive. Not as expensive as staying in many U.S. cities, but higher than Portugal or Panama. Expect to budget $3,500 to $5,000 monthly for a comfortable life. Healthcare is good but limited for complex issues. This works best if you want island life and have a solid retirement income.

Mexico (Playa del Carmen, San Miguel de Allende, or Mexico City)

The good: Close to the U.S., affordable, excellent food, growing expat communities, good healthcare in major cities. You can live well on $2,000 to $3,000 a month depending on the city. Direct flights home are easy and cheap.

The reality: Safety varies widely by location and changes over time. Do your homework and talk to recent expats, not just people who moved there 10 years ago. Spanish is necessary for daily life. Healthcare quality varies, but the top hospitals in major cities are excellent.

What Most Retirement Guides Don't Tell You

You can't just show up and wing it. You need to scout first. Take a 10-14 day trip (I know, limited vacation days are real). Stay in a few different neighborhoods. Use public transportation. Buy groceries. Go to a local clinic if you can tour one. Talk to expats who look like you and share your concerns.

The "it's so cheap!" stories leave things out. Yes, rent might be lower. But setting up your life costs money. Shipping or replacing belongings. Getting the right visa. International health insurance if you're under 65 and not on Medicare yet. Trips back home. These add up.

Being Black abroad is different everywhere. In Lisbon, I felt mostly invisible in a good way. In Panama City, I connected with Afro-Panamanian communities pretty easily. In Barbados, I was just another person. In Mexico, it varied by neighborhood. Your experience will depend on the city, the neighborhood, and honestly, on you and how you carry yourself.

Healthcare continuity is critical. If you have chronic conditions like hypertension or diabetes, you need a solid plan before you move. That means finding doctors who speak English, understanding how to get your medications (names and dosages differ), and knowing what your backup plan is if something serious happens.

You might get lonely. Community doesn't just appear. You have to build it, and that takes effort. Join expat groups before you go. Find Facebook communities. Plan to be intentional about meeting people. Some of us do better with this than others.

Real Talk: Is This Actually for You?

This works best if:

• You're flexible and can handle uncertainty

• You have stable retirement income (Social Security, pension, investments)

• You're willing to learn at least basic conversational language skills

• You can handle being away from family for stretches

• You're reasonably healthy or have a solid healthcare plan

This probably isn't for you if:

• You need frequent specialist care for complex conditions

• You're deeply rooted in your community and family

• You can't handle bureaucracy and things not working the American way

• You need everything familiar and comfortable

• Your retirement income is tight even at home
  

Where to Start

If you're seriously considering this, here's what I recommend:

1. Get clear on your budget. Write down your current expenses and what you actually need versus want. Be honest.

2. Pick one or two destinations that match your priorities. Don't try to research everything at once.

3. Join expat Facebook groups for those specific places. Read, don't just ask questions. You'll learn a lot.

4. Plan a scouting trip when you can. Even if it's just 10 days. Stay in regular neighborhoods, not tourist areas.

5. Talk to your doctor about your medications and health needs abroad. Get this information early.

6. Start learning the language now if you're serious. Even basic skills make a huge difference.
   

Look, retiring abroad isn't a magic solution. It's not all beaches and cheap wine. But for some of us, it's a real option that could mean living better on less money, with less stress, and maybe even healthier.

The question isn't whether it's perfect. The question is whether it might be better for you than staying put.

Want more details on actual costs, healthcare systems, and what life really looks like in these destinations? Check out my book "The $8 Milk Decision" on Amazon, or follow along here at Uncensored Unbothered as I continue documenting this journey.