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In episode 78, spotlights Danny Safran’s masterclass in turning everyday spending into 75 free hotel stays spanning 11 countries—all while juggling a full-time property-management career and family life. Host Ross unpacks Danny’s journey from his first Hilton card to high-tier Hyatt Globalist status, showing how clear goals, year-ahead planning, and the right mix of co-branded cards turn points into deluxe rooms and lasting memories for kids, spouses, and even extended relatives.

The conversation drills into practical tactics: tracking sign-up bonuses with Travel Freely, timing free-night certificates, and layering cashback portals like Rakuten, Viator, and Capital One to “triple-dip” on rewards. Danny and Ross swap tips on leveraging Amex Offers, saving on hotels during big sports events, and easing friends into the game—proving that a measured, family-first approach lets you savor both the journey and the destination.

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Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.