TravelStories Episode 16: Creative Booking

Episode 16: Show Notes.

Award booking is often a combination of haphazard gyrations and creative problem-solving to find the fares that you are happy with and that makes it worth traveling! In this week’s episode, we take the time to discuss our personal experiences and share thoughts on some of the awards-booking search tools we’ve explored lately, including AwardLogic,, PointsYeah, and many more. We then jump in and talk about the recent trips we booked (to Australia and Brazil) using our miles, discussing both flights and hotels and why we made the different (and multiple) tweaks throughout the process. Join the conversation as we share our thoughts and ideas on what works for us and how we approach award booking. Start listening now!  

Key Points From This Episode:

  • [00:20] What’s expected in this week’s episode.
  • [01:00] Our thoughts on some of the new available booking tools.
  • [02:55] Awards search tool comparison and the blindspots of these tools.
  • [08:19] Why we don’t fully trust these tools.
  • [08:45] What makes these tools useful.
  • [10:30] A recap of the tools we’ve already discussed.
  • [12:20] We continue with the tool comparison: starting with
  • [12:45] How Trevor is using ChatGPT alongside some of these tools.
  • [15:00] Our thoughts on PointsYeah and Skypesos.
  • [17:49] Trevor’s power tool.
  • [18:20] We talk about domestic bookings (as they relate to the search tools).
  • [19:00] Things that have helped the most, according to Thomas.
  • [20:20] We explore Thirfty, Straight to the Points, The Flight Deal, and more.
  • [22:00] Looking at the Wikipedia pages for Dulles Airport and how that factored in.
  • [22:25] We pivot and discuss our travel planning for Rio: a fun story.
  • [24:56] Rio: our flights.
  • [26:35] A lightbulb moment for Trevor regarding excise tax.
  • [29:30] The final flight plan (after many tweaks).
  • [32:20] Rio: our hotels.
  • [36:25] Cash plus points option.
  • [38:20] We talk about hotels in relation to airport location and our final decision on hotels.
  • [39:17] Jumping into Thomas’ Australia trip.
  • [41:20] Getting to Sydney, AUS with awards: The (possible) Unicorn.
  • [49:00] This week’s Guess the Fare!


“What I found with these tools is, you really do need to have a whole bunch of them in your arsenal.” — @tmount [0:02:10]

“For me, a lot of these tools, I ultimately don’t trust them.” — @TktweetsKim [0:08:12]

“The [search] tools, I find, are useful in going from scatter-shop to hand-grenades to being able to narrow in.” — @tmount [0:08:45]

“We’ve mentioned again, time and time again, [that] miles and award points are a very inflationary currency.” — @TktweetsKim [0:11:19]

“It’s good to know that these [search] tools exist because it’s not only about doing your own searches, it’s about getting ideas from these different newsletters and other people who are award-booking all the time, or in the community, and know or have certain tips that they can share with us.” — @TktweetsKim [0:21:30]

“Sydney is definitely one of the hardest places to fly on rewards tickets to these days.” — @TktweetsKim [0:41:17]

“Sometimes you find the fare you are comfortable with and then just set it aside and plan other trips.” — @tmount [0:48:42]

“This whole episode (#16) is about all these gyrations and all this creative problem-solving that you have to do in order to find compelling award hacking or award travel itineraries that make sense to you, and present the value that makes them worth traveling.” — @TktweetsKim [0:53:44]

Links Mentioned in Today’s Episode:






Frequent Miler

Thrifty Traveler

Straight to the Points

The Flight Deal



Hilton Rio

Grand Hyatt Rio

JW Marriott

Copacabana Beach – TripAdvisor

Bamboo Airlines

TravelStories Episode 15

Thomas Kim on Twitter

Trevor Mountcastle on Twitter

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