Let me get this out of the way – I love trip reports.  Reading them, that is.  It’s kind of exciting to see what other people experienced on their vacations, whether it’s somewhere I’ve been (bah, they should have eaten at xyz, that abc is a tourist trap!); somewhere I want to go (we’ll do that one NEXT!); or even somewhere I have no desire to visit (I’m not sleeping in that!).  And I’ll often think, wow, imagine how much trip planning probably went into that nice clean report!  I know, it’s a completely boring thought, but it’s where my mind goes.

While I am horrible about writing trip reports – I’ve deleted more drafts than I care to admit – I am at least diligent about writing as I plan.  I never thought to clean it up and publish it, but as my family is planning for next summer’s big trip, I thought why not give some attention to the trip planning process.  After all, one of my stated goals is to make the destination more fun for you by alleviating some of the headaches up front.  With that in mind, I’ll kick off what I hope to be a helpful series on Trip Plans.

At home, I talk about traveling a lot.  It’s the world away from the office, and for some reason, I seem most satisfied with the parts of it I see that involve a plane ride and living somewhere else.  My wife has been not so subtle in reminding me lately that our last couple of trips have been to places that I primarily wanted to see.  Vacation time is a finite resource and it’s her turn to pick.

Vancouver and Seattle, Summer 2015

My wife has great memories of childhood vacations in the Pacific Northwest, but she has not been back in a number of years.  I thought we could fix that this summer with a few touches enabled by our ridiculous points and miles hobby.

For us as a family, picking dates is the most difficult piece of our trip planning, mostly because we have to agree on it before we can do anything.  As I previously wrote about on manufacturing leisure time, we try to take advantage of company holidays to save some vacation time.  Therefore, the plan is to travel around the Independence Day holiday, starting in Vancouver and spending the Fourth of July in Seattle.

Flights:  Boston to Vancouver

A glaring problem with my plan is that we are looking to travel when pretty much everyone else is doing the same.  As a result, awards – particularly the awards we most want – may be tight or non-existent.  Thankfully, we are getting a jump on this and having booked the outbound, we at least know that we’re going somewhere.

The downside to booking this far out is that many programs only load schedules 330 days in advance.  As a result, a late June/early July departure is bookable with American or Alaska now, but the return may not yet be open, depending on the date we depart – this will be a 1 week vacation based on time off constraints.  It is worth mentioning that British Airways loads a full year out, so you can at least search the return and book it with Avios if you’re nervous that it won’t be there at the 330 day mark when American or Alaska will allow you to ticket it.  My approach is to wait and see, especially since I’d like to return on Alaska using their direct Seattle to Boston flight.

Why are we stopping at JFK?

Other blogs have covered the particulars, but there is a great Cathay Pacific fifth-freedom route serving New York (JFK) to Vancouver (YVR).  Cathay Pacific (CX) flight 889 is a daily JFK-YVR-HKG route featuring their 4 cabin 777-300ER, and represents a rare opportunity to fly a top notch premium product without leaving North America.  Cathay Pacific is a Oneworld member airline and also partners with Alaska Airlines, among others, so redemption opportunities exist – especially so since Cathay Pacific is fairly generous in releasing Business and First Class space well in advance.

I had identified this flight as something we “had” to do for at least one direction on this trip.  Thankfully, the availability more or less fell into my lap.  I prefer to use the British Airways tool to find Cathay Pacific award space – American and Alaska’s websites do not show CX online, but BA does.

My strategy was to search first for this segment, using the weekends before, of and after July 4, 2015.  As it would turn out, availability is pretty wide open right now.

5 Business and 1 First over a holiday? Yes!

Most days around the 4th of July show 5 business and 1 first class seat available, which is standard issue for Cathay Pacific.  As Lucky recently wrote, you may find more space opening up in First as the date of departure approaches and the seats go unsold.  I took his advice and grabbed two business seats and the one in first, hoping that 2 more will open up in first next year.  Seeing as how this is my wife’s trip, though, I ticketed her in the first class seat.  If the space never opens, all I ask is that she come slum it in business for just a few minutes with us, even if only to tell us how the 1% of the 1% live.  Real first world problems.

As mentioned, American and Alaska were my two primary options to ticket this.  British Airways and US Airways were also possibilities, based on my current miles and points balances, but for reasons that I’ll discuss below, were not viable:

• American charges 25,000 miles each way in business; 32,500 in first; $25 booking fee and $5.60 in taxes
• Alaska charges 25,000 miles each way in business; 35,000 in first; $12.50 booking fee and $5.60 in taxes
• British Airways charges 25,000 miles each way in business; 37,500 in first; however, BA also charges per segment so we would need to tack on another 4,500 to connect to JFK – easily pricing it out of the picture for me
• US Airways 50,000 miles round trip in business; 65,000 in first; but requires a round trip award and charges fees for virtually any change to an award itinerary, which we would like to avoid

I ended up ticketing with American because I could save a few miles on the first class seat, but more importantly, I had a ton of flexibility on the award to change dates and routing if more seats opened up on another flight or if we wanted to leave earlier.

I then needed to find a way to JFK.  JetBlue is an option out of PWM, but I was looking to incur no additional costs to connect, so my only option became American out of BOS – or so I thought.  Two of American’s award rules came into play here.  The first was that American treats Canada as a domestic flight for award purposes, which meant that the long connection departing Boston at 7am broke the award pricing due to a connection time longer than 4 hours.   Domestically, I was told that was a stopover on the award, and not permitted.  Fortunately, the second rule was that American treats the NYC airports as co-terminals (unlike US Airways, which does not), so we were able to book a BOS-LGA US Airways segment that I absolutely do not intend to fly.

So why would I book a segment I don’t want to fly?  For one, American will let me change to a BOS-JFK segment if award space opens without incurring a fee.  I more or less booked it to preserve the “origin” of the trip out of BOS, hoping that space will open in the future, rather than making the “origin” JFK and incurring a fee if the space did open.  The other is that it gave me a lesson on a third rule (I lied about there being two rules) – American lists the minimum connection time between LGA and JFK as 2 hours, so good luck ever actually flying on a co-terminal change when you need to book it as at least 2 hours but no more than 4.  Still, I am nearly certain that 3 award seats will open up on the valid BOS-JFK flight at some point in the next 320 or so days, especially since we’re happy to sit in coach for that segment.

With roughly equal mileage balances in the American and Alaska programs, I chose to redeem on American because I was able to grab that one first class seat at a lower price.  I also highly value American’s generous award rules, which generally boil down to not incurring any fees unless you cancel the award, change the origin or destination or move the departure date to within 21 days.

Next up, we’ll tackle return flights and hotels.  At the time of this post, I haven’t actually booked those yet, so we’ll pick up the series as that happens over the course of this week.