Booking flights: putting travel experience to use, for better or for worse

When planning and booking my adventures, I balance my efforts between booking it myself and using an adventure travel professional. A straight shot to New York or Paris? I can handle that myself online following the prices for airlines I know provide good value on those routes.

Something more complex, time-consuming, or far, far away? I’ll leave it to the professionals. Unfortunately for them. I’ve found they can access routing or pricing that is simply not available to civilians.

However, gaining international travel experience over the past few years has given me some insufferable quirks. With each flight taken, each airport visited and each airline encountered, the list gets a little longer. Again, unfortunately for anyone who plans travel for me or travels with me.

Flight prices

Planning for my upcoming adventure in Italy is happening in fits and starts. It coincides with a lot of work deadlines, coursework and moving house. As time ticks away, I’ve been watching flight prices increase, so it’s time to hand things over to the capable hands of my adventure travel professional. Again, unfortunately for her.

A traveler’s letter to Santa

What started as a simple “please book a flight” email turned into a veritable letter to Santa:

  • The best I’ve found for the dates I want to travel is a series of [specific airline] flights for about $[price range]. I’d definitely like to stay as close to that as I can, budget wise.
  • Here’s what I’m thinking for dates, I can be a little flexible, especially if it’ll save me money.  Sept 17/18/19: Point A-Point B October 3/4/5 Point C – Point A
  • Of course, I’d like to limit my connections, but will take longer layovers, preferably in Europe, again, if it means saving money.
  • I don’t mind connecting through the US or Montreal, but I’d prefer to go through Montreal over Toronto.
  • Either Air France/KLM/Flying Blue or Star Alliance members would be great, as I’m well into their loyalty programs.
  • My only request is if I absolutely must go through Toronto Pearson, I don’t want to have to change terminals. Pearson is the worst, and the flight that was booked for me last year was a 2 1/2 hour layover with a terminal change which ended in me showing up at T1 just as boarding had started, only to discover my flight had been oversold and I was being bumped. The Air Canada agents at Pearson are simply awful to deal with and I never want to relive that experience if I can possibly help it.

For what it’s worth, I did end the message with “Well, that’s a lot of information to process, I’m looking forward to seeing what you find!” I’m hopeful that my adventure travel professional will find something wonderful for me, after all, as I explained to my friend, “I’m not unreasonable, just specific!”

If you’ve built up some travel experience, how has it changed how you plan and book travel? Let’s chat!


  1. I’m with you on the reason to get a travel agent. Flights to California I can manage and direct to Iceland was no problem. But when I had to book flights to Ghana and wanted to do a stop in Toronto for a wedding on the way there and then a three day stopover in England (six months later)? That was a job for a professional.

    I haven’t done a professional booking in some time, but I’d imagine I’d be as picky as you on my wish list. I have a list of airports I hate (an Air Canada/Montreal experience has spoiled that one for me; San Francisco was a nightmare to navigate) and I want to make sure I’m using members of whatever loyalty program I’ve got.

    • That’s the thing, and I think that’s the future for travel professionals. If they can be experts in convoluted routings and good-price-finding, they’ll make their own case for continuing to exist.

  2. Good luck booking your big trip!

    I’ve never used a travel agent, but once one of those aggregating websites once booked me on a flight from L.A. to Zurich on Monday night, and from Zurich to Barcelona on Sunday night. I got to the airline desk and they were like “Uh, you know your flight left YESTERDAY, right?”

    Nobody (not me, not the airline, not the website, not the airport staff) had any idea what had happened! Maybe a professional would have come in handy…


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