Points Redeeming, Travel Tips

September 21, 2026

Around the World in Five Days: How We Booked an Epic First-Class Trip With Points

Episode Description

Planning an entire trip around one airline seat is a backwards way to travel, and every so often it’s exactly the right one.

My friend Andrea and I have wanted to fly first-class Singapore Airlines Suites on the A380 for years. When we two award seats on their newest first class on a long-haul flight, we built a five-day trip around the world around them, five flights, and almost no regard for where any of it landed on a map. What follows is the whole story, the planning, the flying, and the frankly ridiculous decision-making it took to pull it off.

We get into how a trip like this comes together, why it turns the usual way of planning award travel on its head, and whether spending this many points on a few days of flying was worth it. You’ll also hear our candid take on every cabin we flew, where we agreed, where we didn’t, and which experiences lived up to the hype. 

Whether Singapore Suites is already on your wish list or you just want a fresh way to think about award travel, my hope is you come away seeing that a dream flight doesn’t have to wait for the stars to align over your home airport. Listen in as you learn that sometimes the smartest move is to grab the seat when it appears and let the rest of the trip take shape around it.

Turn your expenses into points and save tens of thousands of dollars a year on your wishlist travel. Don’t miss out! Click here to know more about my comprehensive online program, Points Made Easy.

What You’ll Learn from this Episode

  • How to build an entire trip around a single aspirational flight instead of a destination
  • Why booking award segments out of order is often the key to piecing together a complex itinerary
  • Which first class products are surprisingly bookable for two people, and which are not
  • Why the specific aircraft, not just the airline, determines the experience you end up with
  • How to put orphaned or expiring points to work on a trip worth taking
  • What separates an exceptional premium cabin from one that only looks good online

Featured On the Show

Click here to download the full episode transcript

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Point Me to First Class is the show for professionals and business owners with higher-than-average personal or business expenses, who want to learn to leverage these expenses into credit card points they can spend on travel.

Each week, I share valuable tips, tools, and strategies to help you uplevel your skills earning and redeeming credit card points, so you can expand your travel and expand your experiences.

Start having first-class travel experiences without the first-class price tag.

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