$5500 budget - what would be on your itinerary? Family of 4, 2 boys aged 5 and 7.

I'd fly on day one, go to parks on days 2&3, take day 4 off, go to parks on days 5&6, fly home on day 7.
I'd recommend ASMovies or POP. If you need/want more space/privacy, look at family suites at ASMusic.
We don't use Genie+ or Lightning Lane (already paying Disney too much), and I don't think you'd need to if you go in early December (also my favorite time to go to Disney).
I'd do a grocery order for water, breakfast food (so you can eat in the room which will save money), snacks, etc.
Take Sunshine Flyer RT between the airport and hotel.
Then look at how much $$$ you have for food and decide where/when/how to eat. We usually do QS lunch in the parks and a sit-down table service dinner. Don't forget to think about Disney Springs when thinking about dinner. Polite Pig is NOT a table service restaurant but has great food and feels like you are having a real meal, not just fast food, so I'd consider them for dinner some night also.
 
***We do not need to use any of the budget towards flights, covered w pts.
Where would you stay? (want to hear your opinion on more days at lower cost or fewer days at deluxe?)
How many nights?
Which restaurants would you make sure you hit?
So we're a family of 4, all disney priced adults so with $5500 for the whole trip- that seems like it's either a really pricy shorter stay or a really, really long stay at a value/mod. Most trips we do 3-4 nights which seems to be our travel sweet spot but we have done a full week. I do love WDW and it's a trip we make several times/year but as much as I love it, I can't fathom staying there for 2 weeks.

For us, my kids are teens, I'm a vote for going deluxe with that budget, maybe stepping it up with a party or VIP tour, or other unique experiences and calling it done after about 4 or 5 park days. Now if my kids were still your boys' ages, I'd probably stick with a moderate or even value since the theming really appeals to kids and maybe do an Art of Animation family suite so you have lots of space, two bathrooms and skyliner access. And then still do all the fun extras! Budget some money for a minnie van when you don't want to take the bus to MK, or some nice sit down meals.

So, back to your question- you just need to ask yourself and family a good number of questions that will dictate your trip planning-
  1. Do you want to spend $5500 on a disney vacay?
  2. How long do you want to be at WDW/in the parks, at the resorts?
  3. Do you want to have rest days, mini golfing, water parks etc?
  4. Do you want to sit down for a meal everyday?
  5. What's important to you that a resort have in terms of amenities, food, etc?
  6. What sort of hotel space do you want, you ok with just a motel style room?
  7. What sort of trip do you want to have, slow paced/fast paced, etc.
There are so many variables but we usually use our budget to back into our resort choice and then we sort of build the trip from there since that's the most expensive part outside of tix.
 
So we're a family of 4, all disney priced adults so with $5500 for the whole trip- that seems like it's either a really pricy shorter stay or a really, really long stay at a value/mod. Most trips we do 3-4 nights which seems to be our travel sweet spot but we have done a full week. I do love WDW and it's a trip we make several times/year but as much as I love it, I can't fathom staying there for 2 weeks.

For us, my kids are teens, I'm a vote for going deluxe with that budget, maybe stepping it up with a party or VIP tour, or other unique experiences and calling it done after about 4 or 5 park days. Now if my kids were still your boys' ages, I'd probably stick with a moderate or even value since the theming really appeals to kids and maybe do an Art of Animation family suite so you have lots of space, two bathrooms and skyliner access. And then still do all the fun extras! Budget some money for a minnie van when you don't want to take the bus to MK, or some nice sit down meals.

So, back to your question- you just need to ask yourself and family a good number of questions that will dictate your trip planning-
  1. Do you want to spend $5500 on a disney vacay?
  2. How long do you want to be at WDW/in the parks, at the resorts?
  3. Do you want to have rest days, mini golfing, water parks etc?
  4. Do you want to sit down for a meal everyday?
  5. What's important to you that a resort have in terms of amenities, food, etc?
  6. What sort of hotel space do you want, you ok with just a motel style room?
  7. What sort of trip do you want to have, slow paced/fast paced, etc.
There are so many variables but we usually use our budget to back into our resort choice and then we sort of build the trip from there since that's the most expensive part outside of tix.
So, first, $5,500 won't get anyone a 2-week stay at WDW unless that person already possesses an AP and is on a solo trip, staying at a Value.

Next, OP, please ignore this advice about doing a VIP tour. The absolute cheapest VIP tour is $450/hour for a 7-hour minimum = $3,150. That doesn't include tax and a tip and also doesn't include park admission. You'd blow almost your entire budget in one day.

And, finally, an Art of Animation family suite costs about the same as a Deluxe. At least it has every time I've checked that out. OP, you need a Value resort if you're going to stay on-site. And you really need a discounted hotel rate. General-public discounts show up all the time. As I said in a previous post, check out mousesavers.com, where you can see what rack rates are at all the resorts, when discounts have been offered, etc.

Even though $5,500 is a lot of money (at least, to me, it is), you don't want to blow it all on staying for 3 nights at the Grand Floridian and eating at Citrico's. I'm sure you want to go to the parks and have fun.
 
***We do not need to use any of the budget towards flights, covered w pts.
Where would you stay? (want to hear your opinion on more days at lower cost or fewer days at deluxe?)
How many nights?
Which restaurants would you make sure you hit?
When do plan on going? That makes a huge difference in prices for both resorts and park tickets. You might be able to stay somewhere for a week at the end of August on your budget, or four days at the same hotel at Christmas time or school vacation weeks. People have offered some good advice, but I echo the part about the VIP tour, that would pretty much take up your entire budget without ever checking into a Disney resort.
 

I can see this budget working far better with offsite hotels around Disneyland than in FL. But I’d still look at offsite with that budget.
 
So, first, $5,500 won't get anyone a 2-week stay at WDW unless that person already possesses an AP and is on a solo trip, staying at a Value.

Next, OP, please ignore this advice about doing a VIP tour. The absolute cheapest VIP tour is $450/hour for a 7-hour minimum = $3,150. That doesn't include tax and a tip and also doesn't include park admission. You'd blow almost your entire budget in one day.

And, finally, an Art of Animation family suite costs about the same as a Deluxe. At least it has every time I've checked that out. OP, you need a Value resort if you're going to stay on-site. And you really need a discounted hotel rate. General-public discounts show up all the time. As I said in a previous post, check out mousesavers.com, where you can see what rack rates are at all the resorts, when discounts have been offered, etc.

Even though $5,500 is a lot of money (at least, to me, it is), you don't want to blow it all on staying for 3 nights at the Grand Floridian and eating at Citrico's. I'm sure you want to go to the parks and have fun.
Totally splitting hairs but in August a two week stay, public discount, 12 nights, with 10 days of tickets at an All Star for a family of 4 is ~$4000. $1500 would be tight for all your food but it's doable for folks who don't eat every meal out. And during the same time period, if you did the shorter trip option and did AofA at ~$400/nt, 3/4 park days would put you in around $3800.

In no way did I suggest a two week stay, plus a deluxe hotel and VIP tours and other splurges, that's definitely not doable. However, if they do a shorter visit as I mentioned, 4/5 days, they could most certainly fill in with a VIP tour for parents only, or a dessert party for the whole family. We are a family of 4-disney priced adults and stay at either a moderate or deluxe, usually around 3-5 nights for less than $3k with tix. Our upcoming trip in August is 3 park days, 4 nights at a disney mod for less than $2200.
 
Totally splitting hairs but in August a two week stay, public discount, 12 nights, with 10 days of tickets at an All Star for a family of 4 is ~$4000. $1500 would be tight for all your food but it's doable for folks who don't eat every meal out. And during the same time period, if you did the shorter trip option and did AofA at ~$400/nt, 3/4 park days would put you in around $3800.

In no way did I suggest a two week stay, plus a deluxe hotel and VIP tours and other splurges, that's definitely not doable. However, if they do a shorter visit as I mentioned, 4/5 days, they could most certainly fill in with a VIP tour for parents only, or a dessert party for the whole family. We are a family of 4-disney priced adults and stay at either a moderate or deluxe, usually around 3-5 nights for less than $3k with tix. Our upcoming trip in August is 3 park days, 4 nights at a disney mod for less than $2200.
Agree on the hotel (value) though I think $1500 for food for 13 days and 4 people is not really doable at Disney. Also, you can't just "do a VIP tour for the parents", the price is the same whether it is one person or ten. It is an hourly rate for a max of 10 people, and rates start at $450 per hour with a minimum of 7 hours. That is before tax and tip, as @Miffy mentioned. And those $450 hour days are not very often. Again, without the OP saying when they plan to travel, it's hard to offer suggestions.
 
Get a deluxe without the deluxe price. Check out the Marriott Swan or Dolphin, walk or boat to Epcot and Hollywood Studios. Larger rooms, better dining options. If you or your husband has status with Marriott it is a great use of points and we have generally received a few small upgrades and been treated well. Our status gets us free breakfast for 2 and upgraded internet, plenty of water bottles etc. and the points add up. A great way to use your points for 4 nights and get the 5th free as well.
 
Get a deluxe without the deluxe price. Check out the Marriott Swan or Dolphin, walk or boat to Epcot and Hollywood Studios. Larger rooms, better dining options. If you or your husband has status with Marriott it is a great use of points and we have generally received a few small upgrades and been treated well. Our status gets us free breakfast for 2 and upgraded internet, plenty of water bottles etc. and the points add up. A great way to use your points for 4 nights and get the 5th free as well.
We like doing this! We are titatium so normally get a nice upgrade, but the free breakfast for two is normally easy to pay just for a couple kids meals and it's a great start to the day. Just make sure to figure in the price of parking and the resort fee into the budget because it ups the bill significantly if you don't.

Depending on the time of year you are going depends on what I would do as far as how many days. Also, how does your family typically travel. What type of hotel level are you use to? Will your kids be able to go all day or will they need a break from the stimulation/heat? Are you a group that will want to use the resort amenities like the pool? Are you a sit down family at each meal or will the kids despise stopping to eat?

It's a lot of questions but regardless of budget you will never be able to do it all in one trip, so it's important to make it the most enjoyable trip. Pick 3-4 things that are must does for you and work from there.
 
If you don't have to stay onsite, there's always the Doubletree Suites at Disney Springs. More affordable, more space, shuttle bus to the parks if you don't have a car, nearby to Disney Springs for more affordable dining options. It would definitely help stretch the budget.
 
One option might be to rent points... roughly a week in the least expensive season (September) at Old Key West might cost $3500 for a week (7 nights). Nice thing is the separate bedroom, full kitchen, washer/dryer, and couch in the living room that folds out for the kids. They're really spacious. The kitchen is a great way to save money on food and beverages... making breakfast/dinner in the room and have light lunches in the parks. That would leave $2000 for tickets, so currently there's the 4 day, four parks tickets, which would leave $400 for groceries. There are a lot of fun things to do on property that don't involve going to the parks... just being at the resort can be fun.
 
If you stay off-site and/or rent a house in the area, you will probably have more space to spread out and it will cost far less then staying @ Disney. Access to a kitchen means you can have economical breakfasts in your room before heading off each day. Those savings could provide more flexibility for where you spend the rest of your vacation budget. Pricey VIP tours won't fit in the budget you have indicated. You might also want to adjust the number of days for your vacation if you are having trouble staying within your budget.
 
What is important to you and your children?
Staying on property?
Having more space?
Rope drop?
How many days would you be there?
 
5500 is what we paid for 10 nights at the Poly with deluxe dining in 2010. Man have times changed.
 














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