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    • 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
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      • Gun Laws In The World
      • English-Speaking Countries
      • Safest Places For Retirement
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    • 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
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      Follow Us:

      • Meet Our Experts
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      Overseas Property Alert

      Sign up for our weekly newsletter to receive expert insights on the best international real estate investment opportunities.






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        Buying Real Estate For Cashflow

        • Discover tips and strategies used by global property investing veterans

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        Live and Invest In Spain Conference

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        VALENCIA, SPAIN

        Sep. 17-19, 2025

        PANAMA CITY, PANAMA

        Oct. 15-17, 2025

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        Contact Our Events Team

        Toll-Free U.S. and Canada:
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        From Outside North America:
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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

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        overseas living letter offers affordable retirement guidance
        The Simon Letter Wealth Protection Insights
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        Home Lifestyle

        Finding Our Dream Life Overseas In Cascais, Portugal

        Why We Moved To Portugal

        by Terry O’Halloran
        Jun 30, 2023
        in Lifestyle
        0 0
        Yacht near beautiful beach and marina of Cascais, Portugal

        Adobe Stock/vitfedotov

        My wife and I made the leap. We moved halfway around the world, to Portugal.

        Maybe we were a little crazy, but we haven’t looked back.

        We’d lived in Hawaii for 40 years, and my wife Ann had just retired from her career as a nurse. It was time for our next phase in life, and we wanted to make the most of it.

        We’d saved enough, but we didn’t want to just settle into a “comfortable” retirement.

        We wanted new, different, and exciting.

        Both of us are active and healthy, and we love traveling. We thought a simpler life, where less could be more, sounded very appealing.

        Live And Invest Overseas soon became our guide as we explored the idea of living outside the United States. We acquired country reports and did the recommended research into what expat living might entail.

        When Portugal popped up on Live And Invest Overseas’ list as the best place to live in the Old World, we really became interested. We’d traveled internationally for years but never to Portugal.

        Discovering Portugal

        We knew our criteria for the right place for us…

        A mild climate was important, as was living near the ocean, good health care, safe environment, interesting culture and history, good food, and a reasonable cost of living and of establishing residency. We were also looking for a place where we could get by speaking English.

        We learned that Portugal had it all.

        Our friends asked why we were going to live in a place we’d never seen. Ann would simply reply, “Why not?” She was ready for adventure! We were both ready.

        We sold our house, most of our possessions, packed our suitcases and cameras, and headed into an unknown future where going back was not an option.

        We decided we were all in.

        Portugal’s Algarve region looked interesting, but we wanted to be near Lisbon, at least initially. Once again, we turned to Live And Invest Overseas and their contact in Lisbon.

        We felt like we hit the jackpot with him. He found us a beautiful, fully furnished two-bedroom apartment in Costa da Caparica, with an ocean view and a short walk to the beach, just outside Lisbon, south of the Rio Tejo.

        After three months, when the lease on our rental was expiring, we decided to move closer to Lisbon. This time, Live And Invest Overseas contact found us another two-bedroom apartment with an ocean view in Caxias, midway between downtown Lisbon and Cascais.

        It was a small community with quiet neighborhoods and friendly people. Next door was a large house with lots of trees and shrubs. Living on that property was one of the most beautiful peacocks we’d ever seen. Each morning we watched him stretch his feathers and prance around. You never know what you’ll find in Portuguese neighborhoods!

        Caxias turned out to be too quiet for us. With only a couple of small neighborhood grocery stores, we frequently took the train to Cascais for supplies. It didn’t take long to realize that we’d be much happier in Cascais… meaning it was time to move again.

        Finding Our Overseas Haven In Cascais

        Cascais seemed to have everything we were looking for, and we loved that it is just a 40-minute train ride to the center of Lisbon. LIOS’ contact again helped us find a great apartment with a sweeping ocean view on one side and a spectacular view of the Sintra Mountains on the other.

        This is, without a doubt, our favorite apartment and place in this country. Now we feel like we’re home. We love Cascais.

        Life In Cascais

        There’s so much to see and do here that we feel like we are only beginning to discover the true nature of Cascais and its surrounding areas. Our favorite discovery so far has been the enormous Cascais market on Wednesdays and Saturdays, with fishmongers, bakers, butcher shops, and the freshest seasonal produce you can find at prices easy on the wallet.

        This is a happening place with a strong sense of community.

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        Cascais is also spectacularly beautiful with clean ocean waters, a rugged coastline, white sandy beaches, stone buildings, cobblestone sidewalks, and several parks.

        When the sun or moon rises over the bay, you can feel the romance in the air. My wife and I feel like we’re falling in love all over again. Our favorite pastime is strolling along the bay holding hands.

        The people here are marvelous… friendly, welcoming, and helpful beyond expectation.

        Although we get by with English, we’re trying to learn Portuguese. It’s a challenge but worth the effort. People I meet are willing to help me learn, and the smiles are priceless when I actually pronounce a word correctly.

        We love to walk. It keeps us from getting rusty. One of our favorite walks, 15 minutes from our apartment, is to one of the oldest active lighthouses in Portugal, the Farol da Guia. From there we follow an excellent walking/bike path along the coastline of rugged seaside cliffs into downtown Cascais.

        In the center of Cascais, outdoor cafés, restaurants with seaside dining, and interesting shops abound. In addition to the parks, there are forts, museums, flowers year-round, palm trees, and statues everywhere.

        Summer in Cascais is all about getting outside and enjoying the beaches. This time of year, we share the city with a vibrant tourist crowd from all over the world.

        The winter months are much quieter with mostly just local Portuguese folks to keep us company. We like both seasons and the differences each brings.

        One thing that helps to create the strong sense of community is the annual events calendar.

        All year long we have outdoor concerts and fireworks by the bay. Then there’s a Festival of Light when light artists from around the world project their art on city structures… international sailing races… equestrian events… and each summer cerveja (beer) and sardinha (sardine) festivals.

        Magnificent Lisbon is on our doorstep. This city reminds us of San Francisco with its red 25th of April suspension bridge, trams, and steep, narrow streets.

        We’ve traveled to Lisbon for concerts and great dinners out. Recently we found an excellent Italian restaurant perched on a cliff over the ocean.

        I could go on and on, but you get the idea… we couldn’t be happier.

        Sincerely,

        Terry O’Halloran
        Full-time Portugal Expat

        Tags: Cascaisexpat livingexpatsexpats in portugalLisbonLive in Cascaislive in PortugalPortugalRetire in CascaisRetire To Portugal
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        Terry O’Halloran

        Terry O’Halloran

        Terry O’Halloran is an American expat and photographer, formerly from Hawaii, who found a new home in Portugal. Having lived in a few spots around Lisbon, he and his wife finally settled in Cascais, a nearby coastal community. Together they explore the neighboring areas and travel throughout Portugal enjoying all that the world’s top retirement haven has to offer.

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          Cheap

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          • Kyrenia, Cyprus
          • Hua Hin, Thailand
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          • Las Terrenas, The DR
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