Diversify Your Points And Your Planning For A Winning Vacation Strategy

If you’ve got a million frequent flier miles to burn, you can plan any vacation you want, right?  Right?

Not necessarily.

A conversation with reader (and very good friend) Neil got me thinking yesterday about ideal vacation planning.  I’ve been helping Neil get ready for a trip he and his partner are taking next fall as well as getting him organized for future mile earning.  Before Neil and I got started, he had just about 600,000 US Airways Dividend Miles saved up.  I’m pretty sure he started collecting when Clinton was president as he’s had a US Airways credit card for 20+ years.

Since we started working together, he also added over 100,000 American Airlines AAdvantage miles (thanks to the somewhat defunct 100K Citi Executive offer from a few months ago), about 80,000 Starpoints, and 50,000 Barclaycard Arrival points.  These were all generated from sign-up bonuses, and he’s finishing up the sign-up bonus on an Ink Bold card as well.

Neil wants to book round-trip tickets to Venice next fall for a cruise.  Seems like Neil would be in great shape, right?  Before the diversification, he really wasn’t.  And, he still isn’t just yet because of the large US Airways balance.

You see, US Airways still only allows you to book round-trip award tickets.  So, if he can’t find availability to/from Venice on the days he wants to travel, he’s in a bit of a pickle.  He has added a bit of flexibility with the Starpoints and Ultimate Rewards points he’ll earn from the Ink Bold card.  He needs a one-way ticket from Venice to Istanbul if he can find a round-trip flight to Venice, which he may be able to score by transferring Ultimate Rewards points to United and ticketing an award flight on their Star Alliance partner, Turkish Airlines.  Having both Starpoints and Ultimate Rewards points mean he’ll be able to pick from Starwood, Hyatt and Marriott properties on his vacation.

But, here’s a quick example of a recent family trip I planned.  Diversity was the key here, as well as a good balance of points in a number of different accounts.

I was hunting for a trip to Italy.  I knew we wanted to cover Rome and Venice as well as points in between.  That meant we could start in Rome or Venice and finish up in the other.  As a last resort, I could fly into and out of the same city with a 3-4 hour train ride to reposition myself.  I was armed with (and used):

United MileagePlus miles

Ultimate Rewards points

American Airlines AAdvantage miles

Starwood Preferred Guest Starpoints

Hertz Gold Plus Rewards points

I also had some US Airways miles but I preferred to use the Ultimate Rewards points to find availability out of Washington-Dulles (IAD) to Rome or Venice.  That would most likely involve Lufthansa unless I could find direct flights to Rome in business class on United (unlikely).

After mixing and matching a bunch of different permutations, I booked one outbound flight on Lufthansa (IAD-FRA-FCO) and TWO return flights.  One return was on United from Venice, though not on preferred dates.  I used some Ultimate Rewards points transferred to my United account to make that happen.  The other was on British Airways using AAdvantage miles.  It was the right dates and had the added plus of being on my favorite plane, the Boeing 787 Dreamliner.

The optimal return date had me getting back to Philadelphia (VCE-LHR-PHL).  I was hoping I could find 4 seats PHL-DCA on US Airways and extend that flight home.  I did end up finding them a few months later, and oddly the price of my reservation went down.

For hotels, I used my Starpoints to stay at a couple of wonderful Starwood properties in Rome and Venice.  But, I was trying to figure out if that PHL-DCA last segment was quite right, so I might need to use a few more Starpoints.  The day would start with a late morning departure to VCE from our hotel, then a flight to LHR with a few  hour layover.  An afternoon flight from LHR who get us to PHL in the late evening (around 8pm).  We’d have to wait almost 3 hours for our flight home (or hope to clear security quickly enough and get 4 standby seats on an earlier departure).    That’s a pretty brutal travel day for our two small children.

Those might not be the best options, so I put some backup plans in place.  I’ll hold an award reservation at a Starwood property near PHL airport in case we decide we want to spend the night or end up finding 4 seats on a flight the next morning.

I’m looking at Amtrak tickets from PHL to Union Station in DC.  If the price is too high, I can use Ultimate Rewards points and transfer them to Amtrak.

And, last but not least, I’ll use some Hertz Gold Plus Rewards points to book a one-way rental since it’s only about a 3-hour drive from PHL to our home in Northern Virginia.  While Hertz has had a devaluation, one-way rentals are still one of the best ways to use your Hertz Gold Plus Rewards points.

Certainly, since most of our trip is free, it wouldn’t be the end of the world if I had to pay for a hotel in PHL or maybe a rental car or some train tickets.  But, for those on a budget, having options to keep the trip as “free” as possible is the best bet.

Now, changing reservations can cost you money if you don’t have elite status with an airline.  I’m lucky enough to get free changes because of my status, but not everyone is in that position.  There’s still a silver lining to being diversified, in that if your trip is free, change fees don’t have to be a killer.  Another great friend, Miye, needed some help planning a trip to Japan.  We found connecting flights for her a few months ago and waited until closer to departure when direct seats opened up.  An additional bonus was they were on ANA as opposed to United, which most folks would agree is a step up.  She had to pay a few hundred dollars in change fees, but since her family was flying for free (minus some minor fees), the change fee was a deal compared to paying for three tickets.  It’s also another great example of why you need to feed and water your reservations frequently.  Booking is only part of the work to be done.

Diversity was/is the key to our successful trip planning.  Neil is well on his way to being more diversified and flexible in the future.

It sounds like a lesson in retirement planning, but are you diversified?