I didn't initially plan on booking a Disney trip 140 days from my arrival date, it just sort of happened.
It started when I tried to decide whether I would board a Disney Cruise this fall, or take a trip to Disney World. I checked the WDW website to see if there were even any openings for the Art of Animation Resort available for this November or December. Surprisingly, there were. I immediate searched for one of the Little Mermaid rooms. I happily found that it was available for one set of dates in early December. I pounced on it, and began my journey into planning a Disney trip in less than five months.
Immediately, I realized that I'm somewhat at a loss when it comes to dining reservations. I was exactly 140 days out from my trip at the time of booking, which meant I was behind everyone who made reservations at the 180 day mark. I was able to make reservations for a few restaurants, but the one I really wanted, Be Our Guest Restaurant, was booked for our party number. I tried using the trick of booking reservations at different times with a smaller number, but I couldn't find reservations without there being hours between them. I'm now checking daily to see if anything opens up between now and my trip. If I arrive without a reservation, I plan to continue checking diligently with hopes that I can get us in.
If you're someone who requires specific restaurant reservations, last minute booking might not be best for you. I only have a party of two so, other than Be Our Guest, I haven't had too much trouble. If you're going with a large family, you're definitely going to run into some problems. If you do want to plan a last minute trip, or have no desire for reservations, then I still highly suggest giving yourself at least 180 days between booking and arrival.
One other problem I've encountered is booking an economical flight. This one has caused me the most amount of stress. My chances of finding a cheap flight diminish as the holiday season approaches. Some say that one to three months before a trip is the best time, others say there are no best times. I've found it to be a mixed bag. As prices went up and down, I tracked flight prices regularly and utilized Kayak to keep me notified of any major shifts.
When it comes to flights, if you're like me and need travel details planned all at once, last minute vacation planning may cause you some stress. I couldn't take care of details like Magical Express and arrival and departure day plans until this was handled. Being in limbo until a flight is booked definitely made me slightly anxious. If money is no object or you have airline miles, then acquiring flights might not be as big of an issue.
Finally, I discovered that I'm spending a large amount of my days planning. If I'm not browsing the web or DISboards for information, I'm listening to various podcasts for news, tips, and trip reports. I have the luxury of time to do this, while many people do not. If you're considering booking in a short time, be prepared to plan in that same amount of time.
Despite these hiccups, booking my Disney vacation last minute has proved to be an overall positive experience for me. I ended up with prime holiday dates that managed to fall in the window of time when crowds are low just before the Christmas rush. This also meant that my room rates were relatively low. Of course, I chalk this all up to sheer luck. Honestly, the only thing that could have made it better would have been snagging free dining. Given the gold that I managed to find, I'm incredibly content with what I have.
Should you plan a Disney vacation in under 180 days? I'd advise you against it. It's a lot to handle in a short period of time. If you're considering following me down this rabbit hole, I wish you the best of luck. It's not for everyone. While my experience wasn't awful, there were definitely things I could have avoided had there been a few more months between booking and arrival. I don't know if the trip will go well despite the time crunch. What I do know, however, is that I will be booking far in advance for my next Disney trip.