Here’s an email from my old friend Stephen, currently based in Lubbock, Texas:

We want to take a trip this weekend but I can’t figure something out — whether by plane or by car, I can’t figure out how to find trip packages that will start from Lubbock and take us wherever — all the sites I’m using want me to specify a destination, but I don’t care where we go, I just want it to be cheap.

Stephen identifies a glaring weakness of the travel services world: it’s not set up to help people who don’t know where they want to go.

Dozens of times I’ve contacted various travel agents with a query similar to Stephen’s. The response is usually no better than “well, where do you want to go?” or perhaps “I have cheap flights to Florida sometimes.”

In technical terms, their systems don’t support wildcards as the destination: they can’t, in effect, type “select trip where start = Lubbock and destination = *”. And if they can’t do that, they certainly can’t do “select trip where start = Lubbock and destination = * and hotelprice = cheap and kidvalue = fun”.

Travel is still set up based on the notion that it is difficult, expensive, and requires a lot of lead time. The planning infrastructure hasn’t caught up with “maybe we should go to Europe for the weekend.”

I emailed Stephen back and suggested they head to Santa Fe. It’s about 6 hours drive from Lubbock, is beautiful, and, courtesy of my friend and Santa Fe resident Martin I have a list of interesting things to see and do.

I’ll let you know where they end up.