Award booking awesomeness (Part 1)

Some folks love the challenge of earning frequent flyer points. To me, that’s just business. I do it and I accrue and I move on to the next flight. But when the time comes for redeeming those points, that’s where the fun begins. Part of it is because the airlines really do make it difficult to book awards. Part of it is because there are quirks and tricks and nuances in every program and understanding the rules of your specific program makes a huge difference. And part of it is that I generally feel triumphant when I can beat the airlines at their own game.

I won HUGE last week.

First up, our annual anniversary trip. Now in its 5th iteration, my wife and I have gone somewhere out of town for our anniversary each year. Ecuador, Philadelphia/Washington, DC Norway and Scotland were the previous four. This year’s goal was the Canadian maritime provinces. Turns out they’re a bit too spread out for us to hit as much as we wanted in the long weekend so we scaled back to just Nova Scotia. Not too disappointed about that at all.

With non-stop flights from New York to both Moncton and Halifax it was actually surprisingly easy to find award seats into the region. Our outbound requires a connection in Toronto but we’re waitlisted for the non-stop flight (shown in red on the map) and I’m betting that it clears. Either way, we get where we want to be on the day we want to get there and at roughly the times we want to fly. No complaints there. Coming back we picked Sydney as the departing airport. No, not that Sydney. There’s another one up in Nova Scotia. Being a tiny town with a tiny airport the prices on revenue tickets can be pretty ridiculous. So even though we’re only going a few hundred miles the cash version of these flights was pretty ridiculous. But award inventory wasn’t a problem at all. Connecting in Halifax and then back into Newark at good times and with no real issues.

As an added bonus, there are flights from Sydney to France (in the form of Saint Pierre & Miquelon, shown in purple on the map) that we just might have to try. If the flight schedules work that is definitely on my radar.

Did I mention that these were a pretty good deal in terms of valuation for the points redeemed? I like that the Continental booking engine gives you the offer to pay cash instead of redeeming miles for the trip. But I couldn’t help but laugh when this was the option it presented me:

Purchase this Reservation in Economy for $4,452.46 without redeeming miles

Instead I cashed in 50,000 points and about $100 in taxes for the two seats. I’d say that’s a damn good deal.

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• Award booking awesomeness (Part 2)