For many people approaching their golden years, the decision to retire and relocate is about more than just a change of address — it’s a transformation in lifestyle, priorities, and possibilities. Debra Taylor’s story is a perfect example of how thoughtful planning, research, and a willingness to embrace change can make the retirement dream a reality.
Debra’s Journey to Retire and Relocate
In the past year, Debra Taylor has experienced more change than many do in a decade. Navigating a divorce, preparing for retirement, and planning a major move abroad all at once, she made the bold choice to retire and relocate from Southern California to Portugal.
Her decision wasn’t random. She narrowed her options using a practical checklist:
- Taxes – She skipped Spain because of its wealth tax.
- Climate – Costa Rica was ruled out for being too hot.
- Travel Access – Portugal offered easy travel within Europe, one of her favorite regions.
With help from relocation company Expatsi, she toured Portugal and fell in love with Aveiro — a picturesque canal city often called the “Venice of Portugal.” She signed a one-year apartment lease, hired Viv Europe to manage her visa process, and even completed the required FBI background check. Her youngest daughter’s wish to leave the U.S. was the spark that inspired the move.
Why Retire and Relocate Is Growing in Popularity
Relocating in retirement is nothing new, but political, economic, and lifestyle factors are shifting motivations. More than 3 million Americans aged 65+ moved within the U.S. in the five years leading up to the pandemic, according to the Census Bureau. But now, more retirees are looking beyond domestic borders.
Jen Barnett, co-founder of Expatsi, notes that U.S. politics is now the number one reason people choose to retire and relocate abroad. However, some countries are selective — wealthy, English-speaking retirees aren’t always in high demand, as many nations prefer incoming laborers.
Considering Challenges Before You Retire and Relocate
While the dream of retiring abroad is appealing, experts warn about potential hurdles:
- Rising housing costs and rents
- Limited access to healthcare or community services
- Home modification expenses to support aging in place
- Cultural and language adjustments
Rodney Harrell, Vice President at AARP, emphasizes planning for “future you” — considering mobility, income stability, healthcare needs, and transportation access. “Things can change,” Harrell says. “Your health, ability to drive, or financial situation may not be the same in ten years.”
The Emotional Side of Retire and Relocate
Beyond logistics, emotional connections matter. For retirees with children and grandchildren, the decision to retire and relocate often involves delicate family conversations. Retirement transition planner Elizabeth Zelinka Parsons recommends setting expectations early. Will you be involved in childcare? How often will you visit?
Casey and Dave Bowers, another couple who chose to retire and relocate to Portugal, admit the hardest part isn’t navigating local grocery stores — it’s being away from family. They have three adult children, a grandchild, and another on the way.
How to Plan a Successful Retire and Relocate Move
- Define Your Lifestyle Goals
Financial planners like Chad Harmer advise starting with a “lifestyle audit” instead of a tax chart. Picture an ideal Thursday five years from now — who you meet for coffee, how far the grandkids live, the climate you wake up to. - Research and Visit First
Parsons recommends renting short-term before committing. “It’s tempting to retire where you vacation, but that may not be the greatest idea,” she says. - Budget for Hidden Costs
These include higher insurance rates in certain areas, extra travel costs to visit family, and unexpected healthcare expenses. - Match 80% of Your Routine
Harmer’s rule: When you can achieve at least 80% of your desired daily routine in a location for 80% of the year, you’ve found your spot. - Consider Long-Term Livability
AARP’s livability index can help assess communities based on healthcare, safety, transportation, and social engagement.
Top Benefits When You Retire and Relocate
- Lower Cost of Living – Many countries offer affordable housing, healthcare, and everyday expenses compared to U.S. cities.
- Cultural Enrichment – Immersing yourself in a new culture can be mentally stimulating and socially rewarding.
- Travel Opportunities – Locations like Portugal provide easy access to nearby countries for weekend trips.
- Healthier Lifestyle – Walkable cities, fresh foods, and slower paces often improve physical and mental health.
Trade-Offs to Accept When You Retire and Relocate
Every relocation comes with compromises. You may have to adapt to smaller living spaces, different service standards, and new languages. Family visits may require long flights, and bureaucracy can be frustrating. But for many, these are small trade-offs for the rewards of a new life chapter.
Retire and Relocate: A Holistic Approach
Experts suggest viewing relocation not as an escape but as a strategic choice that supports your overall retirement vision. Whether your motivation is politics, cost of living, or simply a thirst for adventure, the key is balancing dreams with practical realities.
The best approach? Combine thorough research with a willingness to adapt. Test drive your chosen destination through extended stays, talk to locals, and get professional help with legal and tax matters.
Final Thoughts on Why Now Is the Time to Retire and Relocate
Debra Taylor’s journey shows that the decision to retire and relocate is as much about mindset as it is about geography. Her move to Portugal wasn’t just about canals and climate — it was about reclaiming control, embracing change, and designing her own future.
If you’re approaching retirement, now may be the perfect time to ask: Where will I be happiest for the next chapter of my life? Whether you choose a coastal city in Europe, a mountain village in South America, or a small town closer to family, the key is planning with both your heart and your head.
By taking a holistic view of finances, family ties, health, and lifestyle, you can retire and relocate with confidence — turning the dream of a fresh start into a fulfilling reality.