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    Whether you’re looking for fun and sun, a peaceful retirement, or the chance to earn some extra income, you’ve got a real world of opportunity open to you… In short, we’ve done our best to narrow down your best options, but only you can decide the right country for you.

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    The only honest answer is, we have no idea. And neither does anyone else. The only one who can answer that question is you. Here’s the most important thing to understand about budgeting your new life overseas…

    Super Cheap

    • Chitré, Panama
    • Santa Marta, Colombia
    • Phuket, Thailand
    • Dumaguete, The Philippines

    Cheap

    • Medellin, Colombia
    • Boquete, Panama
    • Kyrenia, Cyprus
    • Hua Hin, Thailand
    • The Algarve, Portugal

    Affordable

    • Valencia, Spain
    • Cascais, Portugal
    • Las Terrenas, The DR
    • Pisa, Italy
    • La Rochelle, France
    • Mazatlán, Mexico

    Luxury

    • Ambergris Caye, Belize
    • Kotor, Montenegro
    • The Panama City Beaches
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  • Home
  • Countries

    Top Destinations:

    Whether you’re looking for fun and sun, a peaceful retirement, or the chance to earn some extra income, you’ve got a real world of opportunity open to you… In short, we’ve done our best to narrow down your best options, but only you can decide the right country for you.

    • Spain
    • Portugal
    • Panama
    • Belize
    • Colombia
    • Cyprus
    • Mexico
    • France
    • Montenegro
    • Browse All Countries

    Best For:

    • The Best Places To Retire
    • Health Care Abroad
    • Cost Of Living
    • Investing in Real Estate
    • Establishing Residency
    • Gun Laws In The World
    • English-Speaking Countries
    • Safest Places For Retirement
    • Best Places In Latin America
  • Budgets

    How Much Will It Cost You To Live Overseas?

    The only honest answer is, we have no idea. And neither does anyone else. The only one who can answer that question is you. Here’s the most important thing to understand about budgeting your new life overseas…

    Super Cheap

    • Chitré, Panama
    • Santa Marta, Colombia
    • Phuket, Thailand
    • Dumaguete, The Philippines

    Cheap

    • Medellin, Colombia
    • Boquete, Panama
    • Kyrenia, Cyprus
    • Hua Hin, Thailand
    • The Algarve, Portugal

    Affordable

    • Valencia, Spain
    • Cascais, Portugal
    • Las Terrenas, The DR
    • Pisa, Italy
    • La Rochelle, France
    • Mazatlán, Mexico

    Luxury

    • Ambergris Caye, Belize
    • Kotor, Montenegro
    • The Panama City Beaches
    • Paris, France
  • Resources

    Global Living

    • Living & Retiring Overseas
    • Raising A Family Abroad
    • Foreign Residency & Citizenship
    • Offshore & Diversification

    Making Money

    • International Real Estate
    • Banking
    • Employment
    • Investing

    Follow Us:

    • Meet Our Experts
  • Real Estate

    Buying Real Estate For Cashflow

    • Discover tips and strategies used by global property investing veterans

    Explore Our Latest Posts

    • Learn how to invest and purchase property abroad…

    Go To The Overseas Property Alert Site

    • How To Become Independently Wealthy And Fund The Lifestyle Of Your Dreams
  • Conferences

    Upcoming Events

    • Explore Our Events Site

    Live and Invest In Panama Conference

    Live And Invest In Greece Workshop

    Live And Invest In Portugal Conference

    PANAMA CITY, PANAMA

    Jan. 21-23, 2026

    VIRTUAL

    Feb. 19, 2026

    LISBON, PORTUGAL

    Mar. 25-27, 2026

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    Toll-Free U.S. and Canada:
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    Reach us with your questions by email at: events@liveandinvestoverseas.com

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    Your passport to a life well-lived abroad

    Services

    overseas living letter offers affordable retirement guidance
    The Simon Letter Wealth Protection Insights
    Global Property Advisor Global Investment Opportunities

    Our Customer Service team is here to assist with any questions or concerns CustomerService@LiveandInvestOverseas.com

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Home Countries Portugal

A Letter To Santa

by Jeff and Joch Woodruff
Dec 24, 2025
in Portugal
0 0
Christmas mailbox for mailing letters to Santa Claus.

Adobestock/leekris

It was 1955. We lived on Long Island, NY… our home was an easy train ride away from Manhattan. In those days Mom and Dad could put my older brother and I on the Long Island Railroad and tell the conductor that Blythe, our aunt, would meet us at Grand Central Station.

Auntie Bobbie would take us to lunch at the Horn and Hardart Automat near Carnegie Hall. My brother and I loved putting coins into the slots for each menu item. Then we pulled out the meal item and put it on our cafeteria trays. After lunch we would visit the zoo in Central Park, a museum, or a concert. Every trip into the city ended with a wander through our favorite toy store, F.A.O. Schwartz.

I saw a fantastic rocking horse prior to Thanksgiving that year—a palomino that rocked on springs. The horse had bells that jangled as you rocked. I told Auntie Bobbie that I hoped Santa would bring me one!

No doubt Auntie Bobbie thought she would support my parents when she told me that Santa could not find that rocking horse in time for Christmas. I’m sure today it was the price tag that must have been a concern for her.

I was crest-fallen. Auntie Bobbie was our favorite person in the world. She was the expert when it came to all things Santa. If she said Santa couldn’t deliver, there was no way I would get that palomino.

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The day after Thanksgiving was dedicated to writing letters to Santa every year. We sat at the dinner table with hot chocolate and cookies to write our letters to Santa. I sat quietly and stared at my piece of paper. My older brother, Twain, concentrated on listing all the toys he wanted in his letter… and our younger brother, Tony, scribbled away on his piece of paper creating a drawing for Santa… my piece of paper was blank.

Mom of course noticed that I wasn’t writing anything. As I sipped hot chocolate she asked if there was anything I wanted to ask Santa for. I just mumbled, “No.” She didn’t pressure me for an answer… she figured I would let her know eventually.

As Christmas approached, Mom and Dad kept asking if I wanted Santa to bring anything, but I stayed silent.

My resolve broke at lunch on Christmas Eve. I recall we ate Campbell’s chicken noodle soup. Tears flowed as I shared that I wanted the palomino… but Auntie Bobbie told me Santa couldn’t bring it. Dad soothed my disappointment with some Christmas cookies. Mom calmly left the room and phoned Auntie Bobbie.

The call must have been brief. Auntie Bobbie was ordered to get that rocking horse and take the train out to Cold Spring Harbor right away. Auntie Bobbie delivered.

Dad, Mom, and Auntie Bobbie were up late that night assembling the toy. Years later my parents confessed there were martinis and eggnog involved with the assembly.

An excited little cowboy found the rocking horse by our Christmas tree the next morning. I asked, “How did Santa get me the palomino?” Auntie Bobbie nodded with wide eyes as Dad explained that Santa heard me tell everyone what I wanted out loud yesterday. “It was perfect timing,” Mom added. “Santa was just about to depart in his sleigh. We’re all glad you shared your dream with us.”

That sunny Christmas morning Mom, Dad, and Auntie Bobbie made me a believer in Santa. Today I also understand that the three of them showed me how I could believe in my own dreams, too.

I share this story because I think well-intended folks often toss a bucket of ice-water on our dreams. Several friends tried to convince Jeff and I to abandon our plan to retire in Portugal. Yup, their intentions were good, but they tried to convince us to stay in California. They argued against following our dreams.

Jeff and I knew Santa would deliver the gift of a nice life. We just needed to let him know about the dream out loud before we moved. So, we rejected the perspective of our friends… we didn’t stay in the U.S. We kept voicing our dream out loud, we never turned back, and Santa delivered.

Portugal is indeed everything we hoped for in 2019. Jeff and I are about to celebrate our sixth Portuguese Christmas. Our life in Perafita is magical. We are indeed fortunate. We followed our dream and it led us to Portugal.

The other day we told Santa that we want a new down comforter for Christmas this year. I’m confident it will be under the tree on Christmas morning.

Remember, dear readers, share your dreams out loud. Give voice to ideas, hopes, and fantasies. Santa is listening. And Santa delivers.

Who knows, you might just say as we do, A vida é boa—life is good.

Sincerely,
Joch Woodruff
Portugal Circle Liaison

Tags: Christmas StoriesExpat Lifeliving in portugalMontenegroPerafita
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Jeff and Joch Woodruff

Jeff and Joch Woodruff

Jeff and Joch met in 2007 while volunteering on the board of a San Francisco non-profit organization. And, married in 2013. Joch turned 70 in 2019. So, Jeff suggested a January birthday trip to consider moving to Portugal. They flew to the Algarve, spent a couple of weeks exploring, visited Lisbon for three days and enjoyed a day in Sintra. They added two days and an overnight in Dublin on their return home. After comparing Portugal to numerous other retirement destinations Portugal remained the right decision for both of them. They reside in Braga. Their forever condo apartment is being built as they practice their Portuguese and plot post-pandemic trips around the world.

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HOME

Top Countries

  • Spain
  • Portugal
  • Panama
  • Belize
  • Colombia
  • Cyprus
  • Mexico
  • France
  • Montenegro

Best For:

  • Health Care Abroad
  • Retirement Living
  • Cost Of Living
  • Investing in Real Estate
  • Establishing Residency
  • Gun Ownership
  • English Speakers
  • Safety
BROWSE ALL COUNTRIES

Budgets

How Much Will It Cost
To Live Overseas?

Super Cheap

  • Chitré, Panama
  • Santa Marta, Colombia
  • Phuket, Thailand
  • Dumaguete, The Philippines

Cheap

  • Medellin, Colombia
  • Boquete, Panama
  • Kyrenia, Cyprus
  • Hua Hin, Thailand
  • The Algarve, Portugal

Affordable

  • Valencia, Spain
  • Cascais, Portugal
  • Las Terrenas, The DR
  • Pisa, Italy
  • La Rochelle, France
  • Mazatlán, Mexico

Luxury

  • Ambergris Caye, Belize
  • Kotor, Montenegro
  • The Panama City Beaches
  • Paris, France

Resources

Global Living

  • Living & Retiring Overseas
  • Raising A Family Abroad
  • Foreign Residency & Citizenship
  • Offshore & Diversification

Making Money

  • International Real Estate
  • Banking
  • Employment
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Meet Our Experts

Real Estate

Overseas Property Alert 

 

How To Become Independently Wealthy And Fund The Lifestyle Of Your Dreams

VISIT SITE

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Discover tips and strategies used by global property investing veterans

READ MORE

Explore Our Latest Posts

 

Learn how to invest and purchase property abroad…

EXPLORE

Conferences

Live and Invest In Panama Conference

PANAMA CITY, PANAMA Jan. 21-23, 2026
Learn More About This Event
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LISBON, PORTUGAL Mar. 25-27, 2026
Learn More About This Event
MORE EVENTS

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Reach us with your questions by email at: events@liveandinvestoverseas.com

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  • Hours of coverage  from our latests conferences

Lahardan Books

  • Titles on living and investing around the world

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