Trip Information

Reader Josh is a Disney fan living in Jacksonville. He has an annual pass to the parks in Orlando, but has never travelled to where the magic started: Disneyland in Anaheim, CA. He wants to travel this December with one companion to visit the place where dreams come true on a cheap Disneyland vacation.

Current Program Status

Josh is a newcomer to miles and points, without any travel credit cards or balances in programs, looking for the best place to start.

Our Take

Much like Josh, I too am a huge Disney fan but have never taken the opportunity to visit the parks in Anaheim. That really should change, especially considering how easy it would be, given the results of today’s research! Mickey says dreams come true, and he’s right. Let’s dive in and I’ll show you how:

How to Fly

Southwest Air

Departing from Jacksonville on a cross-country flight? Chances are Southwest is going to offer the most affordable redemption option for us. Sure enough, Southwest offers clearly the best value for this itinerary at the moment.

As you can see, plenty of routes are to be had for 9,600 miles each way per person. Southwest offers 750 miles just for signing up for RapidRewards, which is a great start. We need to find 19,200 miles per person in total to make this work.

Unfortunately, the Chase Southwest cards recently reduced their bonus from 50,000 miles down to 25,000, so they’re not a good choice for us right now. Don’t worry: I’d be shocked if the mileage bonus doesn’t go back up in a few months at most, but that doesn’t solve our immediate need. The best bet for us is once again the Chase Sapphire Preferred, with its 40,000 point bonus after $3,000 in purchases in the first 3 months. More details can of course be found on our Sign-Up Links page.

As we’ve been covering in our series on Ultimate Rewards, points from this card transfer on a 1:1 basis to Southwest in 1,000 point increments. Assuming Josh only earns 1 point per dollar in meeting the minimum spend requirement on the card, he’ll have 43,000 transferable points.

While Southwest is the best option from Jacksonville, there are two more out of Orlando that could make sense.

Orlando to Anaheim

We covered the fact that Virgin Atlantic miles can be used on Virgin America and Delta in our piece sending a reader from Jacksonville to Sydney, Australia last week. The same trick can be applied nicely to this itinerary, as well.

Let’s say Josh wanted to spend a few days enjoying the parks in Orlando before heading out to Anaheim, so he can enjoy a truly memorable Disney experience. Roundtrip flights on Virgin America – a much nicer travel experience than Southwest, however you slice it – can be had for 25,000 Virgin Atlantic miles dependent on availability.

Virgin Atlantic may also be able to track down an itinerary on Delta, either from Jacksonville or Orlando, for the same amount of points.

This is valuable as a backup plan if nothing else, since Southwest redemption levels are based on the cash cost of a ticket, which may rise between today and when Josh has the points necessary to book the trip.

Either of these options would require 50,000 points for both tickets, but if Josh follows our Ultimate Rewards guide, he should be able to boost his point total up without a tremendous amount of strain.

The other option is for both Josh and his companion to apply for a Sapphire Preferred separately and pool their points. From here on, we’ll assume that this is the case.

Where to Stay

Again, some of our old tricks come into play nicely here. Just as with Jarrod’s trip to see the Jaguars play the Rams in St. Louis, Hyatt offers an excellent redemption opportunity for us.

The Hyatt Regency Orange County is located just 2 miles from the entrance to Disneyland, and is a Category 3 property. That means it goes for just 12,000 points per night. These points again transfer on a 1:1 basis from Ultimate Rewards.

Josh might not have the points needed to cover hotel and airfare for two people by himself unless he earns some substantial bonus points, but if he and his companion pool their points for the trip, this is easily achievable. 38,000 points in total must be transferred for airfare; if Josh and his companion each earn 43,000 by simply meeting the Sapphire Preferred’s minimum spend, this leaves 48,000 points, or enough for 4 free nights at this Hyatt property.

Our Recommendation

We’d definitely recommend a Sapphire Preferred for both Josh and his traveling companion in this case. If flight costs remain stable until they can book, Southwest is the best value, but if flight costs rise, having the versatility to take advantage of Delta or Virgin America by virtue of transferring miles to Virgin Atlantic instead of Southwest is a solid backup plan.

Because availability is so good right now, we can safely assume that the Southwest option will remain available. Thanks to this, the bare minimum number of points Josh and his companion will have when combined – 86,000 – is perfectly enough to cover a four day trip, including flight and accommodations.

Plus, the number of miles left over are more than enough to cover a full and enjoyable stay at a great hotel right down the street from the parks, for free! That way, Josh can put all the money he’ll save where it belongs: into the turkey leg stand and towards a mouse-ear hat or two!

Happy travels!