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  • Travel Gear
    • Men’s Holiday Gift Guide – Western Rise

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      Lightweight Merino Gear – Ridge Merino [Travel Gear Review]

      Foehn Brise Pants Review [Travel Gear Review]

      Bluffworks Travel Suit Review [Travel Gear Review]

      Chase Pants from Boundary – New Slim Travel Pants

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    • Coaching Services Reader Success Story

      Personal Award Travel Coaching – Earn and Redeem Your Dream

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Points and Miles

Puerto Natales, Chile – More Than Just the Gateway to Torres del Paine

Puerto Natales, Chile, is most commonly known as the “Gateway to Torres del Paine National Park.”  This small, lakeside town in southern Chile is a…

Santiago, Chile Guide – Three Days incl. Valparaiso

Award Travel Booking – Chile – Santiago & Patagonia

See More

Travel Gear

Men’s Holiday Gift Guide – Western Rise

It’s no secret that we love Western Rise here at Loophole Travel. They make (in my humble opinion) the best clothing for travel and everyday…

MiniMeis Child Carrier Review

Western Rise Review – Diversion Pants, Limitless Shirts, and more!

See More

Dare to Dream

Santiago, Chile Guide – Three Days incl. Valparaiso

Azores Guide – Santa Maria Island with Mantamaria and Bootla

Honest Cuba Travel Guide – 23 Things to Know Before You Go

9 Essential Costa Rica Travel Tips – Know Before You Go

See More

Latest Posts

  • Travel Gear

    Lems Boulder Boot Leather Review – BEST Packable Boots for Onebag Travel

    by Jesse

    Unlike most people, packing is a great joy for me.  I love the challenge of optimizing my wardrobe to fit everything into a small bag,…

  • ItalyTrip Reports

    Florence and Tuscany – Guide to a Few Days in Central Italy

    by Jesse

    Florence is a beautiful city in the heart of Tuscany.  Often overshadowed by Venice or Rome, Florence should not be skipped during your trip to…

  • Travel Gear

    Western Rise Clothing Review – Jacket, Flannel, & Henley

    by Jesse

    We are back with some more gear from Western Rise to share with you! If you missed our first set of Western Rise reviews, covering…

  • Uncategorized

    LAST CHANCE – Earn 35,000 Points – SPG Amex Business Credit Card

    by Jesse

    It’s no secret that Starwood Preferred Guest points are the most valuable in the points game.  For a limited time (until 3/28/18) American Express has…

  • ItalyTrip Reports

    Rome Quick Visit Guide – Vatican, Colosseum, Catacombs, and More

    by Jesse

    Rome, Italy is the last remnant of one of the greatest empires in history. The city sits along Italy’s west coast and is home to…

  • GreeceTrip Reports

    13 Tips for Santorini, Greece – Sunsets, Wine Tasting, Sail Tour, Great Views, and more

    by Jesse

    Santorini, Greece – home of the white-washed buildings and the blue rooftops. This island, in the middle of the Aegean sea, is a romantic place…

  • Temple of Zeus with Acropolis in the Background
    GreeceTrip Reports

    11 Tips for Athens, Greece – Make the Most of a Quick Visit

    by Jesse

    After our layovers in Istanbul and Cairo, we booked two nights in Athens, Greece. When I pictured Athens, I conjured up visions of Hercules, Achilles,…

  • Riding Camels at the Pyramids of Giza
    EgyptLong Layover GuidesTrip Reports

    Cairo Layover Guide – Pyramids with Emo Tours [Long Layover Series]

    by Jesse

    The Pyramids of Giza!! The oldest of the Seven Wonders of the Ancient World! When we started planning our trip around the world, I put…

  • Trip ReportsUnited States

    How to Visit Havasu Falls with Award Points

    by Jesse

    Havasu Falls is easily one of the most beautiful places in the U.S.  The falls are located on the Havasupai’s tribal land, nestled in the…

  • Hagia Sophia, Istanbul, Turkey
    Long Layover GuidesTrip ReportsTurkey

    Istanbul Layover Guide [Long Layover Series]

    by Jesse

    When we told people that we scheduled a long layover in Istanbul, en route from the Maldives to Greece, we got a lot of mixed…

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