Disneyland Dreaming
Disneyland truly is one of the happiest places on earth for my husband and I. Several times over our relationship, including our honeymoon, we've popped down for a few magical days. It's been about ten years since the last time we did this, and both of us are starting to feel like it is time. Yes, we've been to Disney World since then, but it's really not the same. Because I've been to Disneyland so many times, it's a familiar, comfortable booking process for me, but just in case it's new to you, I thought I'd share my steps.
What Comes First?
With most trips, you need to decide whether to book the flight or the hotel first. Most of the time this will land on the side of the flight, but because we are blessed with the ability to fly for free with my daughter's airline benefits (she's a flight attendant), the first piece of this puzzle I need to consider is the hotel. Because of the huge variability in hotel and ticket prices with Disneyland, you'll want to probably research both hotel and airfare before booking either. Now, there are three different ways to go with this, and I'll cover them as succinctly as possible.
Using Points
The first thing I considered was which hotel I could stay at with points. I'm currently saving points for my big 30th Anniversary Australia trip in 2028, so I need to be careful with this. If I were to stay at a Marriott or Hilton property near Disneyland for four nights it would run me between 50,000 and 75,000 points per night, or 200,000-300,000 points for the four-night stay. That's enought for two business class airline tickets to Australia, so I think I'll pass on those. The only decent points redemption option (in my opinion) is the Hyatt House about half a mile from the entrance. That's very walkable (or rollable in my case) and at only 12,000 points per night or 48,000 for the whole stay - including a nice breakfast every day - that's much more reasonable. But points aren't the only option.
Pay with Cash - or Pay Yourself Back!
Many of the dates I'm considering have very reasonable (for Disney) cash prices as well. One nice, quick way to check these is on Google Hotels. Much like Google Flights, you can choose a hotel and then open the dates box and see the base pricing for a standard room on every night of the month. You can also scroll out to future months to see when the best time to go is. That's so much more practical than going onto the hotel's website and randomly guessing which dates to check. IMHO, the best options here are the Best Western Park Place Inn and the Camelot Inn & Suites. They have the best ratings of all the hotels that are directly across the street from the entrance, ideal if you want to pop back to the hotel for a nap or a pool break mid-day. The Best Western looks like about $1,400 for four nights on my dates and Camelot is running about $300 less. Google Hotels will show you several different booking options including booking directly with the hotel or with an Online Travel Agent (OTA) like Expedia or Booking.com. Often, if you book directly with the hotel, you won't have to pay until you arrive. That might work great for you, but I, of course, have a couple of special deals I'm chasing. The first would be a shopping portal bonus, like one through Rakuten **or Swagbucks. Today, they are both offering 10% cash back on some OTAs which adds up when you're talking about a $1,000-$1,500 purchase. This would require you to actually pay the balance due today in order to qualify for the cash back, but I'm not sad about this because I also want to pay in advance in order to Pay Yourself Back for any travel expense with the Aeroplan® Card. This program allows me to "erase" up to $2,500 in travel purchases per year using 200,000 points. I know, I know, I said I didn't want to spend 200,000 points, but I'm not really. For one thing, these points would cover both the hotel and tickets, and I might have a little left over. The other consideration is that I was able to transfer my Chase points over to Aeroplan with a 30% bonus at the beginning of this year meaning I only needed 153,000 points so I'd be getting a very good value for my points. If your eyes just glazed over reading that, suffice it to say that in this case I'm ok with spending the points, especially if it makes my Disneyland vacation close to $0 out of pocket!
Staying on Property
Tickets
Can I book a Disney Hotel Cheaper?
Insurance
Trip insurance is another important consideration. You've got a few options here: a travel insurance company like Allianz, Credit Card insurance, or Disney's insurance. For my husband and I, a mid-priced plan through Allianz, our historical carrier of choice, would be about $224. Another option is to pay for the entirety of your trip on a Chase Sapphire Preferred or Reserve credit card*. Chase recently changed their coverage to say that only the portion of the trip paid for with the card is covered, so the old, "Put $5 on the Sapphire Preferred and it'll cover the whole thing" trick is dead. This means you couldn't take advantage of the Aeroplan pay yourself back program though, and that could cost you much more than the insurance. Lastly, if you book through Disney, you can add on insurance for only $99 per person. The Disney insurance will cover your hotel and your tickets (if booked as a package). Both the Chase Sapphire insurance and Allianz will cover airfare as well, saving you the additional cost of insuring that separately. Keep in mind that most of these hotels will let you cancel up to 4-5 days out for free (check the fine print on your reservation when you make it to be sure) and people typically know by then if they will be unable to travel. A Disney vacation package is only 100% refundable up to one month out, but that would be a refund of both the hotel and the tickets. Under most circumstances, tickets to anything are not covered by insurance, but when booking a vacation package (hotel + tickets) through Disney it becomes part of the pre-paid non refundable cost of the trip that gets covered, and at over $1,200 for two people's four-day park hopper tickets, that's not insignificant. Which will I choose: the Allianz, paying 100% with a Chase Sapphire, or buying Disney insurance? Well, since we're not needing to insure our airfare, our most practical option is to buy the Disney insurance I think. This allows me to use my Aeroplan card to cover $2,500 worth of the trip but still covers the unforeseen, especially important since our trip is so far in the future.
Here's the Thing: There are a lot of things to consider and a lot of moving parts to arrange when it comes to a trip to Disneyland, but that's half the fun for me! As you can see, I revel in hunting down all the options and cost-comparing them, then seeking out little side deals that can bring my cost down further. It's not all about price though, a trip like this is more about the experience. If you can swing it, do Disneyland in style!
* Earn 125,000 bonus points with Sapphire Reserve® or 75,000 bonus points with Sapphire Preferred®. I can be rewarded if you apply here and are approved for either card.
** This is my referral link and if you sign up using it we will each receive $50 once you've made $50 in purchases through the portal.

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