One of the most frustrating things about traveling is watching all your well-laid plans go completely out the window. Hours of planning and preparing, all for nothing. This is why you should actually *keep* preparing for reasonably foreseeable problems that may arise.

I am constantly reminded how unpredictable travel can be. My wife and I have had our share of incidents, from minor delays, to unpredictable driving conditions (read: landslides), to completely canceled flights. Two of the worst incidents include our recent detour around the 101 slide (SEE: So close, yet so far), and being completely hosed by United on our trip to Quebec (SEE: Our First United Horror Story).

Planning for FT4RL

When I booked my recent flight to Orlando for the Family Travel 4 Real Life conference (SEE: Invaluable Disney travel hacks and other things I learned at FT4RL), I was poignantly aware that I had chosen an itinerary with only a 35 minute connection in San Francisco. The ticket was the best I could find to fit my $500 budget with my Merrill Lynch points that only had one connection. It also had good departure and arrival times.

Normally, this would be everything I’d want in a flight. Except I understand all too well United’s track record flying between Arcata and San Francisco. That route may have the worst on time performance of any in the whole U.S. I’m serious. Delays are pretty much inevitable on the route.

My “worst case” plan

Because the late morning flight from Arcata has such an abysmal on time performance (it’s one of the lovely options in Google Flights that gets the “often delayed by 30+ minutes” designation), I made sure I researched some alternate flights. Rather than simply let an agent rebook me into whatever makes sense to them, I like to understand all my options. Being prepared in the event of a delay could save me substantial time and headache.

For example, I knew I would prefer flying part of the way on a connecting flight rather than take the next nonstop flight to Orlando. If I had missed the 12:55 p.m. departure out of SFO, I would have been stuck waiting until a 10:40 p.m. departure! This would be an awful red-eye,  arriving at a little after 7:00 a.m. eastern time. There is no way I wanted that flight, even if it is a nonstop.

Instead, I would prefer to fly to one of United’s hubs. I specifically identified Houston as the best one, mainly because hotels are cheap (in case United wouldn’t comp me), and because there are a LOT of flight options, both from SFO to IAH and from IAH to MCO. More options = less chance of significant delays.

Chicago was a secondary option to Houston. There are just as many flights to Orlando each day. But it would be a slightly longer trip. Either way, I’d given myself enough travel time that an overnight delay wouldn’t kill the trip.

I jotted down some preferred flight numbers for both options, in case I missed the flight to Orlando. I wanted to be able to feed the agent the exact flights on which I desired to be rebooked.

The final precaution

The last thing I ended up doing was changing my reservation in Orlando at the Country Inn & Suites. If I missed my flight and couldn’t make it, I would be out the points. Instead, I planned on either booking an IHG hotel on points at the last minute, or using cash if rates were decent. Orlando was actually one of the best options for earning at least a small number of bonus points from my Q2 IHG accelerate offer, so I opted for cash.

Ultimately, everything turned out fine. The flight out of Arcata left a mere 5 minutes late, which is unheard of. We landed a few minutes late at SFO, and I literally walked off one flight, down the terminal, and onto the other. It was the closest connection I’ve ever had that I’ve actually made.

In this case, planning for “the worst” wasn’t necessary. But I know that things won’t always go that smoothly!