For our flight to Spain, we were already starting out in NYC, which makes flying to Europe much more simple compared to the West Coast. There are usually a variety of award options from the New York area to Europe, and if you are willing to be a bit flexible regarding your choices, then finding an award booking shouldn't be too big of a problem unless you are flying during peak times. San Sebastián is a fairly remote town, and flying into the region from the US usually requires a layover somewhere. The biggest regional airport is in Bilbao (BIO) which is about an hour drive west of San Sebastián. This tends to be our go-to airport when flying into the Basque region (Bilbao is a great city to visit in its own right), but in the past we have flown into Biarritz and taken a bus. We have also taken a bus from Bordeaux to San Sebastián as well. San Sebastián has its own tiny airport, but in my experience flights in and out of there have been pretty pricey.
For this trip I was able to utilize one of my favorite travel options to get to Europe, the fifth-freedom flight. Singapore Airlines has a routing from JFK->FRA->SIN. Because of this, you can book just the first or second segments alone, without having to fly the whole route from New York to Singapore. I was able to transfer 81,000 Chase Ultimate Reward points per person directly to Singapore Airlines to book the ticket from JFK-FRA. This is a great way to travel to Europe, but on one of my favorite Asian airlines. I have written about the good and bad parts of Singapore Air business class in the past, so click on this link if you would like to read more about the hard and soft product.
We thought Jai would sleep the whole time since it was a red-eye, but we were sorely mistaken. We had managed to book the seats with the bassinet, however, Jai stayed in it for a grand total of 5 minutes; he thought it was funny, and instead of sleeping, enjoyed rolling around and playing in it. He did take a long nap on mom, though.
From Frankfurt, we purchased a flight to Bilbao on Lufthansa, which gave us around a 6 hour layover. Not ideal when flying with an infant, but there were just not that many flights to the Basque region that would work with our timings. One benefit of flying on Lufthansa and having the Amex Platinum card is that you get access to the Lufthansa business class lounge when flying a same day Lufthansa flight, even if you're flying economy. This was a great way to pass the 6 hours in relative comfort. We both took showers in the lounge after Jai vomited all over us, and the facilities were very nice and clean.
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