Disney Toddler Travel Travel Planning Trip Reports US Destinations

Daring to Disney: Flights, Hotel, and Car

We're fixing to see the Orlando version of this
We’re fixing to see the Orlando version of this

If you follow me on Twitter or exist within a 50 mile radius of my location, you probably are annoyed by the fact that I’ve been all Disney all the time. I will not deny or apologize for my obsessiveness – it pays off – but I will give a couple reasons for my Disney obsession in this case.

1) I’ve loved Disney World since I was a kid – my parents took me four (or five?) times but I haven’t been since I was a teenager.

2) The way I operate is I need to plan vacations far out in advance, otherwise I panic and overpay.

3) After August, for various reasons, I likely will not step foot on another plane until this trip which is scheduled for January. That kind of layoff is something I cannot abide so I need to make sure this trip happens.

4) It took six years of being my annoying, childish, “Can we go, mom?” self (and 1.5 kids) to convince Jess to go to Disney. I would have gone for our honeymoon if allowed (okay that’s a bit of hyperbole).

Anyway, as I started planning the trip I’ve been receiving a lot of tips and help on Twitter and elsewhere – Leslie, Dia, Haley, and Franklin’s Dad in the forum have been particularly helpful.

Processing all the options at Disney, at least for someone obsessive like me, can be a bit like drinking from a firehose, so I thought I’d write a trip report about planning Disney for a family as a first-timer. I’ll check in from time to time about the planning process – hopefully it will help others save some time! I’m also going for a personal record for trip report length – 7 months. That’s a poorly formed joke in case that wasn’t clear.

BTW, this is what I aspire to – the real pros:


Booking flights was easy this time. I set up a Kayak alert for our dates with a target in mind – <$250 for a nonstop flight. When I first set it up flights were pricing out at $280.

You know how to set one of these up, right?
Kayak alerts are still one of the easiest ways to monitor airfares

Now normally I might set my ceiling lower, like $225 or something, but like I said above, I wanted to lock something in as soon as possible. Sure enough a couple weeks back the price dropped to $250 so I pulled the trigger on three cash tickets. I paid for them with my Citi Prestige – splitting things up so that I could get the $250 airline credit on one ticket and use points for the rest.

In terms of planning, I set it up so we’d arrive at noon and depart at noon – ideal times for flying with our toddler (who, by the way, is also anxious to get back in the air!).


There are a ton of options for hotels – enough to make your head spin. Originally, I booked a room at the Swan (or was it the Dolphin?) using my SPG points, but Dia convinced me otherwise (via this post and Twitter). So it was back to the drawing board.

Basically the main deciding factor for hotels, in my mind, were convenience/theming vs. price. If you stay on-site, you can sign up for Fastpass 60 days in advance (instead of 30), you can ride free shuttle buses (including to/from the airport), parking is free if you rent a car, you get more of a Disney “experience” due to hotel theming (and the promotional materials they send you).

The welcome package really builds excitement (Image via Touring Plans)
The welcome package really builds excitement (Image via Touring Plans)

On top of that, there’s this (which will matter since we’re going in January):

Righty-o. Of course, you’re going to be paying a premium of 40-50% or more as opposed to staying off site. And if you stay off site you can get Air BnBs or condos or all that.

Ultimately, however, I decided to book two rooms at the Port Orleans Riverside (my parents are coming with). We got a rate of $190/night – not amazing but I plan on waiting to see if they post any hotel deals since we’re going in a fairly dead time. At this point we are so far ahead of the game that you can’t even book the hotel online right now (I had to call, the phone agents were lovely FWIW).

I had to make a one night deposit on each room but the hotel is fully refundable so if a deal comes along I’m just going to cancel and rebook (Hotel Strategy 101).

Here’s my thinking. The value properties are probably too motel-y for us to stay in. The deluxe ones are way too baller – I can’t justify $300/night even though I would love to step out of my room right onto the monorail.

You pay a premium to stay in an on site Disney resort, but here the many benefits Disney offers (and their monetary value!) that makes it worth the cost.

Still, I want to stay on-site to get 60 day Fastpass. I also plan to take advantage of the free shuttle – we are renting a car and will use that mainly, but only one car for all of us so if split up it will be useful to have transportation to and from the parks.

Why Port Orleans: Riverside? Well, Dia and Franklin’s Dad both recommended it, plus I liked this website. I like that it has a ton of pools, a food court, and M will love the boat to Downtown Disney. Plus, again, it’s nice to have transportation options beyond our rental car.

So that’s my decision for now but we’ll see how things change. Leslie did tell me this when I asked her if it was cheaper to get a Disney package or buy piecemeal:

Packages for January won’t be open until mid-June (according to the phone agents) so I’ll re-evaluate then. Until then, I’m happy with my decisions! And Jess is happy I have stopped bugging her about whether I can book or not. And M is happy she gets to visit the “little mouse”. Everybody wins.


Just a short note here – for now I have a minivan Autoslashed from MCO. We’ll see how this changes as things get closer in.

Final Thoughts

Even though Haley can do it in a day, it took me almost two weeks to put together this tentative itinerary to Disney. Disney can be super intimidating, at the same time, I like type A-ing this stuff. Hopefully the trip is as fun as the planning – January can’t come soon enough! I’ll update every once in awhile as my itinerary evolves and changes. Until then, feel free to shoot me advice in the comments or on Twitter – would love to hear it!

Other Posts in this Series

Flights, Hotel, and Car

Making Disney Dining Reservations

Saving Money on Disney Tickets

Using Touring Plans (the non-touring plan parts)

Optimizing a visit using Touring Plans’ touring plans

Saving money by staying off site

When a Disney annual pass makes sense

Touring Epcot attractions with a toddler

Touring Animal Kingdom with a toddler

One perfect day at the Magic Kingdom

Dining Reviews

Tips for parents of toddlers and infants

Things I wished I knew before I went to Disney



Just an average joe trying to fly his family for less

14 thoughts on “Daring to Disney: Flights, Hotel, and Car

  1. Here’s my thoughts on staying at the Swan vs. Riverside. I did a nights and flights deal at the Swan and stayed in one of the newly renovated rooms. The resort and parking fee were ridiculous, but it ended up being a good value for us since it was during Easter week. By the way, the new renovations are beautiful and the room was much more spacious than a Disney moderate hotel. I’ve stayed at Riverside twice, once in the Alligator Bayou and once in the Mansions in a princess room. The princess room was nice, but I didn’t think worth the extra money. The one benefit is we were a few steps away from the nightly movie. The room had many spiders and the area was just buggy due to being so close to the river. This was April and I didn’t think we’d need bug spray. The Alligator Bayou was nice, but paying for a preferred room would be a good idea. Otherwise, be prepared to walk a bit of a distance. Check out http://www.portorleans.org. The magic bands are great for charging everything to. I redeemed many, many Arrival miles on my last trip.

      1. I’m not sure. I was listening to another podcast and the individual said that eating outside of the Poly she was attacked by a swarm of mosquitoes. Usually at Disney, bug bites haven’t seemed much of a problem. Next trip, I’ll be taking bug spray.

  2. Hey Joe, We’ve been a few times with the kids. Stayed from Fort Wilderness (basically a camper in the woods) up to Animal Kingdom with giraffe’s cruising by your deck. We’ve enjoyed them all for different reasons. One thing we always did was get up super early so we were first to the site. Then retire back to the lodging over lunch while the lines were the longest, sun honest, etc. Then return well rested into the evening. A good resource book is ‘The Unofficial guide to Disney’. We also found the gates where the characters came out in the morning and knocked out half a dozen or more ‘autograph’ collections in short order. That task can become tedious when lines form. Good Luck!

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