Early planning for 2020 trip to WDW

The last (and only) time my wife and I stayed on Disney property was for our honeymoon. Back then (22+ years ago now), we stayed in Dixie Landings (aka Port Orleans now). It was a wonderful trip, and loved the experience of ditching any transportation other than Disney’s transportation for the week.

Since then, we’ve stayed in Timeshares (a friend’s), Condos, and rented homes. Not nearly as convenient, but a WHOLE lot cheaper…particularly with kids in tow.

But in 2020, my wife and I are planning to return to Disney for our 25th wedding anniversary trip alone. No kids. Just the two of us. And we’re splurging, planning to stay on property. As a result, it will probably be our most expensive vacation ever, with or without kids.

After much discussion, we ultimately decided we want to say at The Contemporary in the rooms with a view of MK so that we watch the fireworks from our room, etc. It has also always been a dream of mine to stay at the Contemporary ever since I first visited MK when I was nine. I remember the thrill of seeing the monorail going through the hotel and feeling jealous of the folks who stayed there.

The other thing we want to do is go during the time of the Disney Holiday party…most likely the first week of December or something like that.

Anyhow, I’m wondering what advice folks might have? Also, I’m wondering how early can you book? When I go to Disney’s website to check pricing for that time period at the Contemporary, I found that the rooms we want are already all booked in December, and it is only Feb. How do we ensure we can get the room we want?

Is there any advantage to booking through a travel agent if we plan to drive down to Orlando and not fly? (We have friends who are travel agents, but I’m not sure if there is any advantage using them.)

And yes…my wife and I are notorious for being early planners. :slight_smile:


Other than starting to save up for the trip and blocking the dates out on your calendar I really don’t think there is much you can do in the way of “planning” almost 3 years out. The furthest out I ever “planned” was about a year as I wanted to rent DVC points from a friend at a specific resort right at the 11 month point. And even then, once I had my room reservation in I didn’t do much until shortly before my 180 day mark when I selected my ADRs. I played around with some rough TPs, but nothing came close to a real “first draft” until I got my FPPs at the 60 day point.

I can’t help with first hand knowledge on early booking of Disney resorts; most of my trips are booked 3-6 months in advance and where I stay is more a function of availability/budget than wanting specific rooms at a specific resort.

I always drive and I have never used a travel agent. I’m not necessarily a “control freak”, but I know WDW as well or better than all but the most dedicated Disney-trained TAs, and if “on the fly” decisions have to be made, I’d rather make them myself vice waiting for a TA to call me and say plan A didn’t work, what’s your plan B. But there are folks who use them regularly and love them…

Yeah, we’re control freaks that way as well. But we also plan our trips well in advance. We usually start high-level planning (budgeting, destinations, etc). 2-3 years out. Then, we’ll start actually making reservations 1 to 1 1/2 years out if at all possible. Sometimes, though, you can’t because they will only allow reservations about a year out.

Anyhow, regarding the Travel Agent question, the only time I used one was for our honeymoon when I was new, young, and in love…I just wanted to make sure everything was perfect. Travel agent found us a good price on airline plus recommended Disney Springs (since at the time, it was about as Value-priced you could get on Disney property).

But since then, we’ve become experts. Still, I wasn’t sure if there might be some special items that Travel Agents have access to that the general consumer might not when staying on property. For example, I do know that Travel agents generally get word immediately when Disney offers their Free Dining Plan on select times, etc., although that wouldn’t apply in our case since I wouldn’t risk waiting for such a deal when we really know where we want to stay and when. If a travel agent can’t offer any advantage, though, I wouldn’t bother asking our friends. I just don’t want to ask our friends and then NOT use them. That would be…awkward. :slight_smile:

We usually use a TA although it is a friend and my trips are easy for the TA as I know the system and what I want. One good thing about TAs, though, is that if you have changes (add a day or want to check to apply a new discount or whatever) and have to call WDW, it is they who sit on hold for the long minutes of lovely hold music :slight_smile:

Historically, reservations and pricing open up for the next year in early summer (i.e. June) IIRC.

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I believe you can make hotel reservations up to 499 days in advance. For instance, if you want to check in on Dec 1, 2020, then you can make reservations about July 21, 2019.

You can only book onsite reservations through 12/31/2018 right now.

That’s for online booking. Once rates and package details are released for 2019, you can do them online. You can call Disney to do dates beyond what shows online, up to 499 days in advance. This is per Disney’s Moms Panel.

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Thanks, folks. My wife did a little digging after the answers here and found a vlog of a travel agent who explained it well.

Basically, if you book a room only, you can do that 499 days ahead of time. But if you want to book a vacation package instead through Disney, you have to wait until they put up their package prices for the following year, which typically happens around Mid-June to July. Once they are up, you can book those packages all the way through the end of the FOLLOWING year (up to 499 days).

The agent always recommended that if you plan to do a vacation package, to NOT book the Room Only at 499 days because you can’t technically add on the package later. Instead you have to cancel the Room Only and rebook.

So, in practice, what we found is that we should be able to make reservations for our vacation package through Disney next summer (~July in 2019) for our 2020 trip.

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As far as using a travel agent, we use ‘Small World Vacations’. (4 times so far) They have always saved us some money.
The benefit of using a TA is you tell them what you want, they book it, and then they will monitor your booking and apply any discount that might come up in the future. They always get the discount announcements a day or 2 earlier than the general public which is great for those ‘limited’ discounts. And they are free, and you can talk to someone directly if you have questions.
We also are planners. So, even though the TA could book your ADRs and any other activities we love to do all that stuff ourselves. That half the fun. So we just use the TA in order to get vacation discounts the minute they come out.