Live and Invest Overseas
  • HOME
  • COUNTRIES
    • TOP DESTINATIONS
      • PANAMA
      • PORTUGAL
      • MEXICO
      • FRANCE
      • GREECE
      • SPAIN
      • BELIZE
      • THAILAND
      • COLOMBIA
      • MONTENEGRO
      • THE DOMINICAN REPUBLIC
      • ITALY
      • ARGENTINA
    • RANKING & GUIDES
      • THE 12 BEST PLACES TO RETIRE OVERSEAS IN 2026
      • CHEAPEST REAL ESTATE
      • BEST PLACES TO RETIRE IN LATIN AMERICA
      • THE BEST PLACES TO RETIRE IN EUROPE
      • BEST HEALTH CARE OVERSEAS
      • BEST COST OF LIVING OVERSEAS
      • QUICKEST AND AFFORDABLE RESIDENCY OPTIONS
      • COUNTRIES WITH EASIEST GUN LAWS
      • BEST ENGLISH SPEAKING COUNTRIES TO RETIRE OVERSEAS
      • SAFEST PLACES TO RETIRE OVERSEAS
    • BUDGETS
      • CHEAP
        • HUA HIN, THAILAND
        • CRETE, GREECE
        • MENDOZA, ARGENTINA
      • AFFORDABLE
        • TARRAGONA, SPAIN
        • SANTA FAMILIA, BELIZE
        • GASCONY, FRANCE
        • SARDINIA, ITALY
        • KOTOR, MONTENEGRO
        • LAS TERRENAS, THE DOMINICAN REPUBLIC
        • BOQUETE, PANAMA
      • JET-SET
        • THE ALGARVE, PORTUGAL
        • PUERTO VALLARTA, MEXICO
  • REAL ESTATE
    • LATEST POSTS
    • THE OVERSEAS PROPERTY ALERT
    • BUYING REAL ESTATE FOR CASHFLOW
  • CONFERENCES
    • UPCOMING EVENTS
      • IN PERSON EVENTS
      • VIRTUAL EVENTS
        • 2026 LIVE AND INVEST IN MEXICO ONLINE WORKSHOP
        • 2026 LIVE AND INVEST IN FRANCE VIRTUAL CONFERENCE
        • 2026 OFFSHORE WEALTH VIRTUAL SUMMIT
        • 2026 LIVE AND INVEST IN COLOMBIA ONLINE WORKSHOP
    • CONTACT OUR EVENTS TEAM
  • RESOURCES
    • GLOBAL LIVING
      • LIVING & RETIRING OVERSEAS
      • RAISING A FAMILY ABROAD
      • FOREIGN RESIDENCY & CITIZENSHIP
      • OFFSHORE & DIVERSIFICATION
    • MAKING MONEY
      • INTERNATIONAL REAL ESTATE
      • BANKING
      • EMPLOYMENT
      • INVESTING
  • STORE
    • SERVICES
      • THE OVERSEAS LIVING LETTER
      • THE SIMON LETTER
      • GLOBAL PROPERTY ADVISOR
      • EUROPE UNCOVERED
      • THE PANAMA LETTER
    • REPORTS
      • EUROPE HAVEN REPORTS
      • OVERSEAS HAVEN REPORTS
      • PANAMA SPECIAL REPORTS
    • LAHARDAN BOOKS
  • MY LIBRARY
Live and Invest Overseas
  • HOME
  • COUNTRIES
    • TOP DESTINATIONS
      • PANAMA
      • PORTUGAL
      • MEXICO
      • FRANCE
      • GREECE
      • SPAIN
      • BELIZE
      • THAILAND
      • COLOMBIA
      • MONTENEGRO
      • THE DOMINICAN REPUBLIC
      • ITALY
      • ARGENTINA
    • RANKING & GUIDES
      • THE 12 BEST PLACES TO RETIRE OVERSEAS IN 2026
      • CHEAPEST REAL ESTATE
      • BEST PLACES TO RETIRE IN LATIN AMERICA
      • THE BEST PLACES TO RETIRE IN EUROPE
      • BEST HEALTH CARE OVERSEAS
      • BEST COST OF LIVING OVERSEAS
      • QUICKEST AND AFFORDABLE RESIDENCY OPTIONS
      • COUNTRIES WITH EASIEST GUN LAWS
      • BEST ENGLISH SPEAKING COUNTRIES TO RETIRE OVERSEAS
      • SAFEST PLACES TO RETIRE OVERSEAS
    • BUDGETS
      • CHEAP
        • HUA HIN, THAILAND
        • CRETE, GREECE
        • MENDOZA, ARGENTINA
      • AFFORDABLE
        • TARRAGONA, SPAIN
        • SANTA FAMILIA, BELIZE
        • GASCONY, FRANCE
        • SARDINIA, ITALY
        • KOTOR, MONTENEGRO
        • LAS TERRENAS, THE DOMINICAN REPUBLIC
        • BOQUETE, PANAMA
      • JET-SET
        • THE ALGARVE, PORTUGAL
        • PUERTO VALLARTA, MEXICO
  • REAL ESTATE
    • LATEST POSTS
    • THE OVERSEAS PROPERTY ALERT
    • BUYING REAL ESTATE FOR CASHFLOW
  • CONFERENCES
    • UPCOMING EVENTS
      • IN PERSON EVENTS
      • VIRTUAL EVENTS
        • 2026 LIVE AND INVEST IN MEXICO ONLINE WORKSHOP
        • 2026 LIVE AND INVEST IN FRANCE VIRTUAL CONFERENCE
        • 2026 OFFSHORE WEALTH VIRTUAL SUMMIT
        • 2026 LIVE AND INVEST IN COLOMBIA ONLINE WORKSHOP
    • CONTACT OUR EVENTS TEAM
  • RESOURCES
    • GLOBAL LIVING
      • LIVING & RETIRING OVERSEAS
      • RAISING A FAMILY ABROAD
      • FOREIGN RESIDENCY & CITIZENSHIP
      • OFFSHORE & DIVERSIFICATION
    • MAKING MONEY
      • INTERNATIONAL REAL ESTATE
      • BANKING
      • EMPLOYMENT
      • INVESTING
  • STORE
    • SERVICES
      • THE OVERSEAS LIVING LETTER
      • THE SIMON LETTER
      • GLOBAL PROPERTY ADVISOR
      • EUROPE UNCOVERED
      • THE PANAMA LETTER
    • REPORTS
      • EUROPE HAVEN REPORTS
      • OVERSEAS HAVEN REPORTS
      • PANAMA SPECIAL REPORTS
    • LAHARDAN BOOKS
  • MY LIBRARY
Live and Invest Overseas
Portugal On €2,000/Month →
Live And Invest In Portugal

World's #1 Retirement Haven

Live and Invest Free Report

Enter your email to get your FREE guide instantly!

🔒 We respect your privacy. Unsubscribe anytime.

  • Best places to live—from Lisbon to the Algarve
  • Comfortable retirement on €1,500–€2,000 / month
  • Cost of living about 30% below much of Western Europe
  • One of the world's safest retirement destinations
Home Countries Portugal

Dream On

by Jeff and Joch Woodruff
Nov 28, 2025
in Portugal
Google Add us as a preferred source on Google NO AI POLICY NO AI
Share:
Facebook X
Sunrise over Historic Lisbon

Adobestock/Dimitri

Dreams really can come true. As you likely know, yesterday was Thanksgiving. Thanksgiving is all about stories for me. Thanksgiving means dreams, too.

Thanksgiving has been part of my “Retirement in Portugal Story” since 1979. If retiring overseas is a dream for you I think you might enjoy this story. So, settle in, dear readers, and read on, or should I say dream on.

Woodruff family meals include stories. My parents encouraged conversation at meals—it was their way to get my brothers and me to slow down, stop gulping our food, and connect. Stories at the dinner table always accomplished their objective and my parents were gifted in asking us about our day to get the sharing started.

Thanksgiving in the Woodruff family when I was young was a meal on steroids, which offered ample time for many stories. We lived outside of New York City until I was halfway through grade school. Bundling up and watching the Macy’s Thanksgiving Day Parade was an annual tradition shared with our aunt who lived in the city followed by a feast with lots of stories shared around the table.

When 1979 rolled around, I was single and working in hotel/resort marketing and management. Thanksgiving was just as important to my 30-something adult as it was to me as a child. My annual Thanksgiving dinners included friends enjoying the parade on TV and feasting on a huge turkey.

But 1979 was a different animal all together. I had been invited by the State Department to travel to Portugal on a hospitality industry trade mission. We were booked on a red-eye flight to Lisbon that left New York at the end of Thanksgiving Day.

I traveled to Manhattan the day before Thanksgiving. I settled into the hotel our family always used in the theatre district—the Wentworth. I left my suitcase on the bed and rushed to the box office of the Uris Theatre to buy a last-minute ticket to Sweeney Todd. Success, I scored a house seat for a wonderful experience—Angela Lansbury’s Mrs. Lovett.

Still humming about meat pies filled with “a little priest” the next morning, I stored my suitcase with the Wentworth’s bell staff and joined the crowds waiting for the start of the parade.

It was warm-ish for New York in November, and a little fog was lifting. Perfect weather for the parade. I couldn’t wait for the snoopy balloon. I was experiencing Thanksgiving live in New York, something I hadn’t done since I was seven. Despite the warm weather, there were chestnut vendors scattered along the parade route. Every piece of nostalgia was in place.

I was a very happy fella as I took a cab to JFK Airport, which I was still calling Idlewild Airport—old habits die slowly for me. The beginning of this trip had worked out well.

At this point in the story, gentle readers, I need to admit that I did not want to go to Portugal. I had never been to Portugal. It was the worst time of the year to be away from my job at the resort. This was when outstanding contracts had to be finalized before customers got swept up with the holidays and the start of a new year. I did not want to be away from the office for the first two weeks of December. No way.

Get Your Free Portugal Report Today!
Simply enter your email address below and we'll send you our FREE REPORT — Portugal: The World’s #1 Retirement Haven.
We Value Your Privacy! We will not share your email address with anyone else, period.


I was told that I had to go. According to the VP of Operations for our management company, we could not tell the State Department that I wasn’t going on the trip. No way.

After a fun overnight in Manhattan I now felt I was being delivered to the gallows. A trip to Portugal that could create a nightmare for my job back in the States. I settled into the plane and tried to sleep as we flew to Lisbon.

I woke as the plane descended to Lisbon on a sunny Friday morning. I was greeted at the airport by a Portuguese host and guided via limo from the airport to the Tivoli Hotel on Avenida de Liberdade.

I recall the morning sunlight was magical. Colors were intense. The air was warm, the pace was gentle, the weather reminded me of spring, not November.

I suddenly felt I was in Manhattan in the 50’s, when I was a little boy. The calçada sidewalks seemed to glisten in the light. There were flower vendors, fruit stands, and roasted chestnut vendors. Poof! The dread about being away from my office disappeared. I was in Portugal and I liked everything I saw.

The following two-and-a-half weeks were an experience of a lifetime. The members of our small trade mission bonded with our Portuguese hosts. Friendships developed, stories were shared, correspondence continued for years after, photographs and postcards were exchanged.

We visited the Algarve. We dined. We wined. We laughed. We cried. We listened. We talked, and talked, and talked. We walked, and walked, and walked. The best ingredients for stories for the rest of my life.

At our last banquet everybody shared farewell remarks. Glasses of wine were raised, and toasts were delivered to the success of our time together. I stood up to thank my new friends. Tears filled my eyes and I blurted, “This isn’t goodbye, because I plan to retire to Portugal. I will return.”

My Portugal Thanksgiving story has been shared at Thanksgiving dinners through the years. My dad believed that anything we say out loud will eventually happen. “The universe listens,” he would say. Forty years later, I made good on my promise to retire in Portugal.

Portugal is indeed everything I hoped for in 1979. Perhaps it could be for you, too.

So remember, dear readers, share your dreams out loud. Give voice to ideas, hopes, and fantasies. Tell strangers, family, friends. Do it at Thanksgiving dinners, at lunches, at breakfasts…

And who knows, you’ll might just be saying as we do, “A vida é boa—life is good.”

Sincerely, 
Joch Woodruff
Portugal Circle Liaison

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.

Get Your Free Portugal Report Today!
Simply enter your email address below and we'll send you our FREE REPORT — Portugal: The World’s #1 Retirement Haven.

We Value Your Privacy! We will not share your email address with anyone else, period.
Our Expertise Unlocks The World

quick links

  • Best Places To Live
  • Best Places To Retire
  • Finding A Job Overseas
  • Real Estate

LIOS Resources

  • New To LIOS
  • Ask An Expert
  • Media Center
  • Contact Us
  • FAQs
Sign up for our free daily e-letter, Overseas Opportunity Letter, and get your FREE REPORT: The 12 Best Places To Retire Overseas In 2026

We Value Your Privacy! We will not share your email address with anyone else, period.

As seen in

US Logos
© 2025 – Live and Invest Overseas™ – All Rights Reserved.
About Us / Contact Us / Privacy Policy / Terms / Unsubscribe
Facebook-f X-twitter Youtube Linkedin-in Instagram
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
  • Investing
Meet Our Experts

Real Estate

Overseas Property Alert 

 

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

VISIT SITE

Buying Real Estate For Cashflow

 

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

2026 Live And Invest In Mexico Online Workshop

Online Aug. 22, 2026
Learn More About This Event

2026 Live And Invest In France Conference

Online Sept. 25-26, 2026
Learn More About This Event

2026 Offshore Wealth Summit

Online Oct. 14, 2026
Learn More About This Event
MORE EVENTS

Contact Our Events Team:

Toll-Free U.S. and Canada:
1 (888) 627 8834

From Outside North America:
1 (443) 599 1221

Working Hours
Monday – Friday 08:00 am – 17:00 pm EST.

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

Store

Overseas Havens Reports

  • Expats' comprehensive destination guides

Conference Kits

  • Hours of coverage  from our latests conferences

Lahardan Books

  • Titles on living and investing around the world

Services

  • Overseas Living Letter: Affordable Retirement Guidance
  • The Simon Letter: Wealth Protection Insights
  • Global Property Advisor: Global Investment Opportunitites
VISIT OUR STORE

Free Report

FREE Report

The 12 Best Places to Retire Overseas in 2026

Simply sign up for our FREE daily Overseas Opportunity Letter, and we’ll immediately email you our editors’ latest research report… absolutely FREE

We Value Your Privacy! We will not share your email address with anyone else, period.

LIBRARY

Follow Us:

© 2008 - Live and Invest Overseas - All Rights Reserved.

Book Cover
User

From the desk of Kathleen Peddicord
Founding Publisher, Live and Invest Overseas

Live And Invest In Portugal
World's #1 Retirement Haven
Inside Your Free Report:
  • The best places to live, from Lisbon and Porto to the Algarve and Silver Coast
  • How retirees live comfortably on €1,500–€2,000 a month
  • Why Portugal's cost of living is about 30% lower than much of Western Europe
  • Why Portugal ranks among the world's safest countries for retirement
Enter your email to get instant access to your report.
You’ll also receive our free daily Overseas Opportunity Letter.
100% FreeNo obligations
Unsubscribe AnytimeOne-click unsubscribe
Privacy ProtectedYour info is never shared
You Could Live Well In Portugal On €2,000 A Month...
Find Out How →
RETIRE OVERSEAS AND LIVE LIKE ROYALTY
Sign up for FREE to learn how. Plus, check out our FREE report on THE 12 BEST PLACES TO RETIRE

We Value Your Privacy! We will not share your email address with anyone else, period.