How I Didn’t Pay for Disney

I just got back from a short trip, surprise!  I flew out of Providence last week to spend some time with family in the Orlando area.  We also spent a few days at Disney World!

Of course, there are some other places I would have liked to check off my list first, but it was great to see everyone.  Some family from South Dakota made the trek as well, so I was excited to go!

That’s the good news.

The bad news?  I started booking this trip before I really got into travel hacking.  This means I spent, ahem, a less than ideal amount of money on the trip.  I could have absolutely maximized my value from points and miles, and then gotten to Disney for much less.  There are plenty of people out there saving buckets of money on Disney trips, and I wanted to brainstorm a bit on how to spend less at Disney too.  Who knows, maybe I’ll go again one of these days!

As I mentioned, I did use the Barclaycard Arrival+ for some of the travel, and was able to redeem some miles there.  I cut $500 off an $810 Southwest bill.  May not be big, but still a step toward a fatter wallet and a fuller passport.  Hmmm, I like the sound of that…

Anyway, I thought it would be fun to speculate, so let’s see how what else I could have done.  For this post, I’ll just look at some Disney resorts and flights BOS-MCO or PVD-MCO.

Places to Stay

The two major categories here are Disney resorts, and off site properties.  Staying on Disney property definitely has its benefits:  longer park hours, ease of access, less travel time, almost legendary customer service; but it isn’t right for every traveler.

Fixed-Value Cards:  Disney resorts are almost entirely Disney-owned, so there’s no easy way to use points or miles for the resorts, other than fixed-value cards.  Although I didn’t redeem Arrival+ miles for our resort, I could have.  I charged the $200 deposit to the card, and confirmed that the charge qualified for the travel miles redemption.  We charged part of the resort bill to my girlfriend’s Discover it Miles, but we could not redeem miles towards it.  I’m not sure about other cards and eligibility though, so be sure to do some research first.

The Swan and Dolphin Resorts:  These properties are on Disney property and considered Disney World resorts, but are operated by Starwood.  You get the best of both worlds, Starwood service and points, Disney perks, what’s not to love?

Non-Disney Hotels in Disney Springs:  There are a few options around Disney Springs too.  These properties include a Hilton, a DoubleTree, a Best Western, and a B Resort & Spa.  This is a good middle ground between the accommodations mentioned above and staying offsite.  Guests still benefit from some of the Disney benefits, like being close to the park, but you don’t get to take advantage of the extended “Extra Magic hours.”

Staying Offsite:  There are tons of hotels in the Disney area, and in Orlando.  Any of those are an option.  Just choose your the brand you like and you can use all sorts of points for your stay!

How to Get There

Let’s assume I want a direct flight from Boston Logan (BOS) or Providence TF Green (PVD) Airports.  I typically fly out of these two, and direct flights are much, much easier to manage from a speculative stance.  Our options are JetBlue (from PVD or BOS), Southwest (PVD), and Delta (BOS).

Opening one of the Southwest or Delta cards should help.

Southwest:  Chase runs a trio of Southwest co-branded cards.  The Premier would be the one to get, with a fairly regular (once or twice a year) bonus of 50,000 Rapid Rewards points.  BOS-MCO runs just under 17,000 RR one way, and from PVD it’s about 16,500.  Pretty close.  The flights are more than Delta in miles, but the miles are also easier to earn, so it’s kind of a toss up.  Depending on when I was booking, I may even have enough points (through spending on the card and flying) to qualify for the Southwest Companion Pass.

Delta:  Delta partners with American Express for their cards, and there’s a number of options.  For my plans, I’d have to go with the  Gold Delta SkyMiles card.  There’s typically a bonus of 25-30k miles for nominal spend, the annual fee is waived the first year, and you save a little money on in-flight purchase, etc.  These benefits are pretty standard for entry-level airline cards.  I’ve mentioned before, I don’t particularly like Delta (to be honest, not sure why) and I don’t find Delta serving many of the routes I want to fly.  Verdict:  I probably wouldn’t fly Delta.  But if I did, I’d open the card.  25,000 SkyMiles would get me one of the three roundtrip flights I needed.

JetBlue:  Although not as big as Southwest and Delta, JetBlue offers solid availability on flights from both airports to Orlando.  For credit card bonuses, JetBlue is in limbo for the moment though,  as they are in the process of switching their card partner from American Express to Barclaycard.  The papers have already been signed, but the full shift won’t occur until sometime in the next month or two.

Fixed-Value Cards:  Cards like the Barclay Arrival+, Chase Sapphire Preferred, and Discover it Miles all enable the user to redeem miles earned for statement credits against travel expenses.  This is the route I took.  I earned 40,000 Arrival+ miles from the standard sign-up offer, and another 10,000 Arrival+ from spending and other activity.  I redeemed those 50,000 points for $500 towards my $810 total bill for Southwest.  In short, I saved almost 62% off the sticker price!


Hindsight is 20/20.  The one good thing I did?  I opened up a Chase Disney Rewards card for the $50 gift card after first purchase, and to save 10-15% off of some purchases at Disney.  Card members also get access to exclusive sessions and photos with certain characters.  Trust me, the little guy is going to be stoked to meet Kylo Ren in Hollywood Studios.  With the new application rules for Chase cards looming over us though, maybe even that wasn’t a great idea…

I booked the flights back in October, just when I was discovering the world of travel hacking.  My point is:  I’m sure you could find better prices to Orlando.  Good luck on your next booking!

Next up I’ll provide a more detailed look at the Disney trip, and crunch the budget numbers, just like I did with Peru!


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