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The First Few Bookings

We're holed-up in the dining room with laptops, phones and our best friend - google.com!  Our mega-spreadsheet - dubbed "the oracle" - is fired-up and our credit card at hand - where would we be without VISA?!

We've collected a few 'best practices' - hope some of them help you with your trip plans.

Flights and Accommodations 

There's a catch-22 in planning any trip - what do you book first - accommodations or flights?  The way we see it, there are a few key constraints to consider:
  1. Airlines post flight schedules up to 11 months in advance
  2. Flight prices will fluctuate leading up to departure date - you want to buy at the right time
  3. If you book a flight 11mo ahead, it's schedule is likely to change at least once before your departure date
  4. Some accommodations offer free cancellations/modifications whereas cheap flights tend to be more rigid
  5. Cheap flights are almost always non-refundable and non-cancellable
  6. Some flight resellers offer 'after market's cancellability
  7. The most flexible fares often come direct from the airline as opposed a reseller
  8. Airlines treat you better when you buy direct from them

Our Strategy

If we can, we book cancellable accommodations, then we book flights. This works very well in the 3rd world and less industrialized countries where accommodation providers are more flexible/hungry for your business.
If the local situation doesn't allow for cancellable accommodation,  we book our flights first and then book accommodations with 'shoulder days'. 

We bravely buy non-cancellable flights because when you're moving 5 people, every additional dollar multiplies 5x... a super-saver flight at $250/each compared to its cancellable equivalent at $350/each might seem a worthy insurance policy, but consider that the extra $100 multiplies out to $500 total - that's $500 that could be spent at your destination on a memorable, enriching experience rather than lining the pockets of airline execs.

To score the best fares, we pre-load all our flights into our favourite mobile-friendly flights app - Hopper.  We use many, but we like Hopper because it alerts us with a mobile push-notification when flights we're planning to book have reached their lowest expected prices - just like Google flights, but more mobile-friendly.

Thanks to Hopper's push notifications, we can exchange a quick text to confirm who's going to book a flight and then, one of us does a quick comparison of fares across our favourite sites - from budgetair.com to sky scanner.com and Hopper itself. 

We've found Expedia, Hotwire and most sites that cater to North-Americans expensive.  Our flights get booked in the many months leading-up to departure, when the are cheapest.... so some flights won't get booked until our trip is underway.

We've looked into One World, Air Treks and other bundled flight providers...  but, we need more control and the ability to buy the cheapest fares.  We find flight options ourselves, on our phones... while we're doing other things... like watching the kids or over lunch hour at the office!

Bundled providers offer excellent service, but either don't fit our budget or don't offer the flexibility we can get with a DIY solution.  We have saved thousands of dollars on flights thanks to savvy timing. 

Flight resellers, like Hopper, simply pass-on the airline's cancellation/change policies/penalties... so we recommend you take a quick look at your fare's baggage allowance and other terms to discover any hidden costs.  Usually, this means you'll have to hit the airline's website... If a flight reseller finds us a flight, we always look at the airline's website to see if we can buy the flight directly from them, even if it costs a few dollars more, so we benefit from better customer service.

Family Tip

We use pre & post-flight 'shoulder days' at either end of a flight leg if we aren't spending much time in the airport's metropolis.  These shoulder days allow us to get to an airport with some wiggle room.  This is especially useful with kids - they just can't shift gears quite as quickly as we can!

If, for example, a leg has us on a remote island, ferrying back to the airport in bad weather might become unpleasant if not impossible.  That extra day of wiggle room puts one night of last-minute 'shoulder' accommodation at risk in case of a flight schedule change or inclement weather.

Activities

We book key activities early enough not to miss out on them but no earlier than that.  Our travel is about experiences - missing important ones is something we avoid.  We often book low-risk accommodations nearby to make sure we have a convenient and affordable place to sleep that's within striking distance of our activity.

Our Planning

At this stage, our itinerary is still pretty fluid - we're planting pillars around which the rest of our trip will pivot.

Tonight we booked an elephant sanctuary excursion in Chiang Mai Thailand! 


Next we'll be booking nearby accommodations we've already picked-out.  We'll be doing our Thailand leg with some very good friends of ours, so we're hoping to find a large enough Air BNB or VRBO for two families - 9 people in total.  Very exciting!


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