Planning my first magical trip

[traveler in training]

Hey everyone I'm new obviously. My name is Heather and I'm so glad I found this site. I am a single mom and I've been wanting to take this trip, well forever. I am becoming a bit of an over planner due to the fact that a Disney trip is expensive for a single mom like me.
I already am planning on the deluxe dining package as we are both food lovers and I love the idea of ordering whatever, wherever, without thinking about the price. I also think this will help with using the 2 table credits when we want/need. I also am almost 100% positive I want to stay at the POR because I have heard it is a little more quiet and the grounds are very pretty. I like the magnolia terrace building. Seems a little fancy, so I will feel like i am getting something special with my money. My son just wouldn't benefit from the value resorts theming. It's a little too juvenile for both of us and Im not sure the price difference is that much.
So here is my dilemma. I am torn on when to go. I know it has to be next year for starters. My son is turning 13 on September 29th (next year). I like the idea of going then because I feel the crowds will be decent. I also would love to catch both the food and wine fest and the not so scary halloween! I think it would be so much fun to surprise him for his birthday I.E. Just drive to the airport with luggage hidden in trunk! I am very concerned with the weather for this time of year. I live in Louisiana myself so I know today was a very HOT day. We have had some not so hot feeling days over the last 2 weeks though.
My other option would be for Christmas week(the week leading up to Christmas). The benefit being he would not have to miss school and the weather would be significantly better. The problem with this option is that I would expect the crowds to be just ridiculous. I also would miss the option of having down time at the resort pool.
I am so torn!!! Any advice would be greatly appreciated! Thanks in advance

 

[traveler in training]

I'm a little surprised I have not received any replies yet. Not sure if I posted this wrong or in the wrong place?

 

[MissDisneyDora]

Hello Heather! First of all congratulations on planning your first trip to WDW. I'm sure you will have an amazing time. POR is a fantastic resort and has a lot of fans. Its very spread out, quiet and has great amenities. Be sure to check out Yehaa Bob Jackson one evening while you are there, also the carriage rides that you can do in the evening are lovely.

In terms of when to go, I would be inclined to say that September might be the better of the two options particularly as it centers around your son's B-day. And as you say, you would be able to do both Food and Wine Festival as well as MNSSHP. If you are foodies (which I am gathering you are with the deluxe dining package) then I am sure you would get so much out of this. I'm just back from a September trip and yes, it is still hot and humid but I didn't think it was as bad as my June and August trips. Also crowd levels will not be as heavy as at Christmas.

I've never been at Christmas and you bet that its on my bucket list- but for a first time trip, I would prefer the more chilled out September option. I have a sneaking suspicion that you guys will go back- so maybe you make an x-mas trip your reason for trip number 2!

Either way you are going to have an incredible time. I have 4 trips as a single mom under my belt so if there's any way I can help- just give me a shout.

x
Dora

 

[traveler in training]

Thank you so much for your reply MissDisneyDora. It is great hearing perspectives from people who have been there/done that so to speak. I can only speculate at certain things. I am going to book my vacation now!

 

[Heather Jensen]

I've never been, but I've heard Christmas time is awesome! We're doing our first holiday trip there this Thanksgiving and we can't wait!

 

[TGM]

Hello! Going from Sept. 29th- 5th is a better option, because of the crowds. You mentioned that this is your first time to WDW, so you don't know what WDW crowds are like.

If you go in December, it will be like this. Imagine the smallest room on Earth, that you feel claustrophobic in, with a painting on one wall. And it's about 60˚. Then, add about 100 people, and then wait two hours to see the painting.

That is what Disney in December is like.

The weather in late Sept. is not that bad. I have a friend who goes the first week of Oct. every year, and he never complains about the weather.

Good luck, and have fun!

 

[traveler in training]

Thank you for all of the replies. I just booked my trip for Oct 1st-7th! I am beyond excited. I don't know how I am going to keep this a secret from my son until then. I will just have to come on here and let it all out.

 

[sunshinemelody]

Hi Heather! So happy to see someone else is planning their first trip to this magical place. It's my first time planning as well, however, I've been once back in 2013. I didn't know how much I would love Disney, but I fell so very, very hard.

I wish you all the best with your planning! And I'll be sure to be on the lookout for any pre-trip reports that you may have!

 

[traveler in training]

So much work to plan but such a fun process in IMHO

 

[sunshinemelody]

So much work to plan but such a fun process in IMHO

Definitely.

Are you feeling overwhelmed? I certainly am!

 

[traveler in training]

I am actually at ease for now. The tickets are purchased... well deposit is paid! This is an accomplishment for me because I have been saying I am going to go for the past 5 years now. I am finally going to make it! I have been trying to involve my son in the planning which is fun. It will still be a shock to him when we actually go because I have planned before. I know in the back of his mind he is thinking it will be another year of not going. My plan is to stop talking about it a few months before I plan to go so that it leaves his mind. I imagine I will start obsessing hard core again when I get closer to my 180 day mark. Then I will be a nut job for sure trying to make sure all of the details and kinks are worked out and making sure every detail is thought of. I am one to try to plan to the minute so I need to figure out how to be "ready and prepared" but not too structured as to not leave room to improvise. I guess with it costing so much and being hard for a single mom I want to make sure I get the most out of this trip and utilize every minute the best way I can to make the trip seamless.

 

[sunshinemelody]

I am actually at ease for now. The tickets are purchased... well deposit is paid! This is an accomplishment for me because I have been saying I am going to go for the past 5 years now. I am finally going to make it! I have been trying to involve my son in the planning which is fun. It will still be a shock to him when we actually go because I have planned before. I know in the back of his mind he is thinking it will be another year of not going. My plan is to stop talking about it a few months before I plan to go so that it leaves his mind. I imagine I will start obsessing hard core again when I get closer to my 180 day mark. Then I will be a nut job for sure trying to make sure all of the details and kinks are worked out and making sure every detail is thought of. I am one to try to plan to the minute so I need to figure out how to be "ready and prepared" but not too structured as to not leave room to improvise. I guess with it costing so much and being hard for a single mom I want to make sure I get the most out of this trip and utilize every minute the best way I can to make the trip seamless.

This is exactly how I feel!

I know my boyfriend is starting to get excited about it, but I fear that he's worrying that I'm all talk and no action on this one (which he knows I'm not, but because this a real expensive trip, probably). However, I've been including him in little things and now I'm cooling it down so that he won't be so bogged down by all of this information being thrown at him for all sides. And I just want to plan every second of every day, but I know that I can't, so I definitely feel you on this one.

Maybe try figuring out small little things right now (oh, what we resort to to keep ourselves sane) like breakfast items and where to grab groceries and how, if you're doing that sort of thing. Or, writing a little list of things that you want to DIY before the trip or even grab (e.g, wet wipes, glow sticks, etc) just so you don't feel so frazzled coming up to the 180 day mark when ADRs come out. I feel as though it's going to lift just a little bit off my shoulders, since I'll feel so inundated to go hard figuring out times for my ADRs about one-two weeks before I have to submit them. And then when the 60 day mark comes for FP+! Oh gosh, I'll definitely want to have gotten everything by then. Can you tell I'm a worrywart? I'm wringing my hands right now, ugh.

Anyway, sorry! Didn't mean to worry you about these things! *hides*

I know that you're going to do a fantastic job planning this for you and your son. I hope that this trip makes him the happiest little boy ever.