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The 12 Best Places to Retire Overseas

Live Better Overseas
for Less Than You Think

Live and Invest Free Report

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  • The retirement havens expats love most
  • Strong healthcare, infrastructure, and lifestyle
  • Climate, culture, and daily life insights
  • Monthly budgets from about $1,400–$3,000
Lief Simon

Lief Simon

Lief Simon has lived and worked in 7 countries on 5 continents and traveled to more than 75 countries. His real estate investment career began with a $5,000 down payment on a three-flat building in Chicago. Less than three years later, Lief sold the building for a leveraged return of 3,000%—$150,000 in profit after closing costs and commissions.

From there, he turned his attention overseas and has bought property in 24 countries including France, Croatia, Portugal, Ireland, Belize, Spain, Argentina, Cyprus, Romania, and beyond. Thanks to his decades-long career as a global property investor, Lief has built a multi-million-dollar portfolio that includes rental properties, significant land holdings, and 7 personal residences.

Lief has established residency in 3 countries and acquired a second passport from Ireland.

In 2008 Lief and wife Kathleen Peddicord made the most important investment of their lives—a 215-acre oceanside finca, known as Los Islotes. There, on Panama’s largely undiscovered Veraguas coast, they’ve installed underground electricity, water, and internet and built a forever family home that sits at the heart of their ultimate vision: a gold standard private residential community for those in search of a true safe haven escape.

Lief’s latest book, “Cowboy Millionaire—The New American Pioneer,” collects all the wisdom he has learned in three decades of living and investing outside America.

He offers advice on international diversification in his twice-weekly Offshore Living Letter and monthly Simon Letter dispatches. For real estate investment opportunities, check out his monthly Global Property Advisor service.

If you’d like to meet Lief in person, join him for one of our upcoming in-country conferences. You’ll find further details here.

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Book Cover
User

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

The 12 Best Places to
Retire Overseas in 2026
Live better overseas—for less than you think.
Inside Your Free Report:
  • Where expats are already thriving around the world
  • Destinations with strong healthcare, infrastructure, and lifestyle
  • Climate, culture, and daily life in each location
  • Real-world monthly budgets—from ~$1,400 to ~$3,000
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