Flights vs. Hotels: What to Book First Using Points

#17 We tackle one of the most common and confusing decisions when planning a points and miles trip to Japan: Should you book your flights first, or your hotels? The honest answer? It depends. And in this episode, I break down how to decide based on what you personally value most. What we cover in this episode: Why I usually book flights first and when that mindset is starting to shift The role flexibility plays in getting great value with points and miles When it makes sense to prioritize business class flights When specific hotels (like the Park Hyatt Kyoto) should come first How peak seasons like cherry blossom season can change your strategy Why booking one way flights instead of round trips gives you more control How positioning flights (flying through nearby countries) can unlock better redemptions Real examples of economy vs. business class tradeoffs especially when traveling with a child I also walk through the award search tools I personally use (and wish I found sooner) to make planning less overwhelming and way more visual whether you’re searching for flights, hotels, or both. This episode isn’t about chasing perfection or luxury for the sake of it. It’s about building a strategy that fits your travel style whether that means better flights, better hotels, or simply more trips to Japan over time. If you stay flexible and plan ahead, points and miles give you options and that’s where the real value lives. Tools & Resources Mentioned in This Episode These are the exact tools discussed in the episode to help you find award availability and plan smarter: PointsYeah – Flight award search tool https://www.pointsyeah.com/ MaxMyPoint – Hotel award availability & calendars https://maxmypoint.com/ Rooms.aero – Hotel award alerts (great for high-demand stays) https://rooms.aero/ Seats.aero – Advanced award flight search (especially business class) https://seats.aero/ Thrifty Traveler – Award & deal alerts from major airports https://thriftytraveler.com/ Google Flights – Route discovery & price comparison https://www.google.com/travel/flights?gl=US&hl=en-US FlightConnections – Visual route maps for positioning flights https://www.flightconnections.com/ Rewarding Routes Stan Store → https://stan.store/rewardingroutes Instagram → https://www.instagram.com/rewardingroutes/ Email → [email protected]