Trip Planning

Some people love to do their own trip planning – getting into the weeds of which hotel has the best location for the best price, checking again and again for the best flights.  While others prefer to leave it to the experts take care of the details.

We’ve done both.  I’ll admit there’s a comfort knowing that if there’s an issue with transportation, or hotel, or whatever – it’s someone else’s problem to deal with.  Knowing that someone else is taking care of whatever paperwork needs taking care of.

I like getting into the weeds.  So armed with my spreadsheet (which gets improved with every trip), I like to do my own research and planning.

With the help of Google Flights, SkyScanner, and Expedia I start the hunt with searching for the best flights.  This part can take the longest and if you can be flexible reap the best savings.  Simply by moving a flight by a day or two can save hundreds, if not thousands of dollars.  With the added bonus of staying in a country an extra day or two!

For accommodations we generally use Booking.com.  We found it quite useful while travelling through Ireland booking hotels only a couple of days in advance, and we’ve been using it ever since.  We liked the fact that you could find not only hotels to stay in, but B&Bs and even a bunkbed in a summer camp!  Who knew?

Like all the services out there they have great filtering, a mapping feature (to ensure you’re close to the action), and make it easy to book the accommodations.  Plus, they have a loyalty program that can offer discounts on certain bookings.

Sometimes the most challenging thing to plan, is what are we going to do all day everyday.  Recently I’ve been soliciting AI to help fill in these days.  I can tell it things like which days we’ll be travelling, where we will start and end, are we on a train or in a car.  Then in a few seconds it tells me all the things we should consider – plus it’ll offer to build me an itinerary. 

Now, AI is not perfect, it doesn’t nail every detail, every time.  But it’s really good at doing the initial brainstorming and getting things started.