This week on Wonderland on Points, we’re joined by Ross Alcorn — better known as the Itinerary Boss — to talk about turning big life expenses into even bigger travel rewards. Ross shares how he and his fiancée strategically used their wedding hotel block, rehearsal dinner, and other wedding costs to rack up massive points, including IHG free nights they’re putting toward a Grand Cayman trip.

We also dive into how Ross approaches real estate, renovations, and everyday expenses with a points-earning mindset, plus the redemptions that have taken him everywhere from Bali’s Alila resorts to future adventures in South Africa and Portugal. Along the way, we swap destination dreams, talk about the newest Hyatt and Kimpton openings, and explore how loyalty programs like IHG can stretch travel budgets further than you’d expect.

Whether you’re planning a wedding, a home project, or just your next vacation, this episode is packed with inspiration for turning ordinary spending into extraordinary travel.