A $100 Singapore stopover and a second vacation — reader success story

Today I want to share a story from TPG reader Anirudh, whose creativity saved him tens of thousands of miles while also setting up a second vacation:

A few years ago, I was gearing up to make a KrisFlyer redemption on Singapore Airlines business class for a solo holiday to Germany at a round-trip cost of 170,000 miles plus taxes from Singapore, until I discovered that I’d be on the waitlist for the inbound flight and couldn’t make the redemption right away. I decided to split the itinerary up into two one-way redemptions for 85,000 miles each and no difference in taxes. While waiting to clear the waitlist, I heard some buzz in the local miles community about what eventually came to be known as the $100 stopover trick, and it didn’t take long to connect the dots.

With my next holiday already planned, instead of a one-way back to Singapore where I live, I booked my return flight from FRA to MEL via SIN for 105,000 miles one-way, adding in a six-month stopover for a fee of $100. Had I booked these as separate round-trips, I’d have spent a total of 286,000 miles, but the stopover trick meant I only spent 248,000 miles with no difference in taxes, saving 38,000 miles in the process. That’s like buying miles at a mouthwatering 0.26 cents per mile!

The neat part of this trick is that award tickets could be rescheduled for free at the time (they now cost $25 to reschedule, in no material way altering the value proposition of this trick) and are valid up to one year from the date of my FRA-SIN flight. Even if I only knew where I wanted to go on my next holiday of the year but knew not when, this trick would make sense. If you play this right, you could go from one holiday to another (so long as they are less than a year apart), effectively buying miles dirt cheap every single time.

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There are two things I really love about this story, in addition to Anirudh's incredible creativity and attention to detail. The first is a general but often-overlooked benefit of stopovers. Normally when you think about getting a free stopover on an award ticket, the obvious "win" is getting to visit two destinations for the price of one. However, stopovers also give you much more flexibility and make it easier to find award availability. Finding nonstop business-class award space on Singapore Airlines from Frankfurt to Melbourne can be quite a challenge, but it's much easier when you can search separately for one seat to Singapore, and then weeks or even months later for the connecting flight.

Related: Maximizing stopovers and open jaws on award tickets

The second thing I love is Anirudh's willingness to plan two vacations at once, though like he said all he had to do was pick the second destination, and he could change the dates for a nominal fee assuming there was award availability. While Anirudh is based in Singapore, this strategy can be extremely useful for U.S.-based travelers with some flexibility in their schedules. Some of the best premium-cabin fare sales we see between the U.S. and Europe are only valid on tickets originating in Europe and flying west. You normally need to book a round-trip to get the lowest prices, so next time we see a great sale, consider splitting it up into two trips. Fly to Europe, enjoy your vacation, and fly back to the U.S. using the first half of the cheap fare. Then, use the return leg to fly back to Europe months later and kickstart another vacation. Often times, taking advantage of the best deals requires a flexible approach and a willingness to think outside the box.

I love this story and I want to hear more like it! In appreciation for sharing this experience (and for allowing me to post it online), I’m sending Anirudh a gift card to enjoy on future travels, and I’d like to do the same for you. Please email your own award travel success stories to info@thepointsguy.com; be sure to include details about how you earned and redeemed your rewards, and put “Reader Success Story” in the subject line. Feel free to also submit your most woeful travel mistakes. If your story is published, we’ll send you a gift to jump-start your next adventure. Due to the volume of submissions, we can’t respond to each story individually, but we’ll be in touch if yours is selected.

Safe and happy travels to all, and I look forward to hearing from you!