keys to the kingdom : how, where + when.

Pssst: Be sure to check out all of our updated tips, here.Howdy, everyone! We’re back with our Disney series this week, and excited to start the first segment here at THH. {Yes, I have resorted to occasionally using abbreviations for our full name. Chalk it up to my sudden laziness as it pertains to keyboard usage} If you missed last week’s intro, please feel free to click on over.  But today, along with my oh so brill comrades, we wanted to have an overview and start with the basics. Today’s topic:

How long, Where and When…to stay at Walt Disney World. 

One big obligatory disclaimer: I wanted to start again by reinforcing that this is just our take on it…opinions based on our own experiences. If planning a trip, decide what your ultimate goals are, based on what you think your own family can do, what you’ve saved for, and other various whatnots that I know you know. Take us all with one big grain of salt, and adapt them to what you want to do. It is your trip, after all.

How long: 

If you live more than five hours away, the one thing we all agreed upon: at least six days. And this isn’t counting travel time.


Prices drop drastically after the second day with tickets to the park, so if you’re concerned about them, that always helps. Why did we all concur on this one topic? We all have young children. For the sheer avoidance of meltdowns and exhaustion, we found that a stretched out stint certainly helped with trip planning. And our own sanity.

I’m a big believer in going all out, when I do Disney. This means I don’t have to drag my tired children all because we leave in three days. Need a nap so you can actually enjoy? Go take one. The parks will be waiting after you take a 2.5 hour break with your exhausted little ones. Want to wait in line to meet Rapunzel? And then Ariel? Do it. We simply found that we wanted our children to be able to experience all that they wanted while they were there, without feeling rushed. If there’s one thing we found, the parks are overstimulation central. So we recommend you take your time, and enjoy.

As you all probably know, WDW has four parks. Not accounting for the water parks. My family, personally, could spend three days alone, in the Magic Kingdom, as my six year old wanted to ride Splash Mountain about fifteen times. And then pirates. And then the Haunted Mansion, and then…It’s just where we’re at right now. All the while, Emerson {3} and Malone {2} were obsessed with Winnie the Pooh. Oh, and let’s not forget the single most exciting event that is the Monorail. Because we stayed for so long, we felt like we were able to enjoy the little things, too. One morning, Malone woke up early, so Jamin took him and they rode the monorail. Malone was in his pajamas. It’s Disney World, so you can kind of do that. We let it become a child led vacation, and even though {my biggest admittance} I had to let go of my own expectations {hello former employee dreams of fabulousness control freak} they had the time of their lives…and we felt like we could afford them the time to do that.

Where to stay:  Our takes. 

Off site experience : There are so many amazing hotels in Orlando at every price point and so to help stay on budget one year, we decided to stay off site. Even with renting a car instead of taking the Disney Magical Express from the airport, we were going to be save quite a bit of money. We stayed at a really nice hotel that was within a 5 min drive of The Magic Kingdom. At the time of this visit I was 34 weeks pregnant with our 3rd child, we had an 18 month old, and a (barely) 4 year old.

While our hotel was a short car ride away from The Magic Kingdom, we did not factor in the time to park, board the shuttle to the ticket and transportation station, ride the monorail to Magic Kingdom and then start our day. We tried on that first day to take the kids back to the hotel for a nap, but by the time we got to the car and unloaded them at the hotel, they were both awake from their power naps and ready to go. Meanwhile, my swollen feet were just getting ready to sit in some cool airconditioning. For the rest of the week, I would take the stroller and sit in various restaurants at the park we were visiting that day while my son
cat napped.

We also really missed the extra magic hours. It was very hard to explain to our 4 year old, why we were leaving when so many other people were staying. We’re those people who let the kids take a nap during the heat of the day, then go back and close the park down with less crowds…and more importantly, less summer heat.

Was it ideal? No. Did we save money? Yes.

Was it as magical as staying on site? No.

We decided that while our kids are young and need naps, strollers, backpacks and the whole nine yards… we would spend the extra money and stay on site. With all of these trips under our belts, we’ve found that, for us, it’s worth saving up, and going all out.

Fave on site property : Bay Lake Towers at Contemporary Resort


On our last visit to WDW, we stayed in a 1 bedroom at Bay Lake Towers. We had a 1 bedroom unit, which was honestly bigger than our first married apartment. Each unit at Bay Lake Towers has a full kitchen, which was great for breakfast. Had we not scored the free meal plan on this visit, the kitchen would’ve been a great place to do sandwiches for a quick lunch before nap time.

The main perk to Bay Lake Towers is, of course, it’s proximity to Magic Kingdom. You can actually walk to the entrance, quicker than the monorail ride. Most rooms have a view of Cinderella’s castle,  and being able to look out the window and see the castle, was amazing. Especially for the kids.

One money saving tip: when making hotel plans, plan to stay at an off site, or cheaper hotel the night your arrive in Orlando if you choose to drive. When you get up and moving the next morning, simply drive to your Disney hotel and check in. You may check in any time, however your room may not be ready. You can leave bags in your car or store them with the bell service. However you will receive your key to the world, (your park tickets/room key/dinning plan) and can begin taking advantage of Disney transportation, and enjoying the parks.
Also for checking out, in order to save money this year, we checked out of our room at bay lake tower in the morning but stayed at magic kingdom all day. At the end of the night we walked back to the hotel where our car was waiting and drove to an offsite, cheaper, hotel that was near downtown Disney. This allowed us to enjoy downtown Disney and then start the drive home, while also saving money.

In my humble opinion, staying inside Disney World is the way to go.  

Yes, it is more expensive. However, there are so many perks to staying on site that make it worth your while. From the Magic Express to the unmatched customer service and transportation options, I feel that you truly get what you pay for.

That being said, here is a quick breakdown of the hotel categories within Disney World:

Value Resorts : most basic yet affordable hotels within DW

Moderate Resorts: one step up from the value resorts.  Affordable and pretty basic hotel.

Deluxe Resorts: very nice yet good bit more expensive hotel option

Deluxe Villas: very nice condo-like hotel option within DW

Value resorts: I’ve stayed in a couple of the value resorts in DW (All-Star Sports and All-Star Music) and these resorts can be described as a large fun, affordable hotel with all rooms opening up to the outside. The rooms are all spread out in separate buildings, some buildings being closer to the main lobby and others being closer to the pool, etc. Each of the value resorts have their own large food court located on site where you can find a variety of foods for breakfast, lunch, snacks, or dinner which is very convenient. If you’re on a tight budget but want the true Disney experience, stay at one of these resorts.

Moderate resorts: in my opinion are not much of an upgrade from the value resorts. I’ve stayed at the Coronado Springs and Caribbean Beach Resort. True, you get a little bit of a larger room and possibly a larger bathroom, but the overall feel and layout is almost exactly like a value resort.  Instead of a food court, however, there is a sit down restaurant, on site. Again, this is just my opinion, but I still prefer to have a food court with a wider variety of options… especially if kids are involved. The value resorts have a more fun themed approach and the moderate resorts are a little more “growny,” but all in all, I don’t think that it’s worth it to pay the extra when deciding between a value or moderate resort. Save your money here to eat at California Grille one night : )

Deluxe resorts: These resorts are without a doubt, more expensive, but are also without a doubt, way more luxurious. I have had the honor of staying at the Contemporary, Grand Floridian, Boardwalk Inn, Yacht Club, and Beach Club. The hotel rooms are all larger and nicer, with more amenities. You will find multiple restaurants on site and possibly a coffee shop or ice cream shop as well. These hotels are very conveniently located to the parks as well and have more transportation options (such as riding a boat to a park, walking to a park, or better yet- riding the monorail to a park).  If it works with your budget, STAY IN A DELUXE RESORT OR VILLA. If it does not work with your budget, go value resort!


Favorite hotels and why: My favorite place to stay would have to be the Boardwalk Inn. I LOVE the look, feel, and theme of the hotel, but what I truly love is the actual outdoor boardwalk which comes to life at night with beautiful lights, music and entertainment. There are many different restaurants to choose from on the boardwalk as well as some adult night life, a grocery market, gift shop, and a very yummy ice cream and candy store. Don’t forget about the carnival type games on the boardwalk overlooking the water!

If luxury is the way you want to go, however, (say for a honeymoon, anniversary, or older children) the Grand Floridian is the way to go. It’s the most upscale and lavish hotel on site. You can expect higher end restaurants, linens, the whole nine.  They truly do it up right at the Grand Floridian, which is why it is usually the most expensive place to stay.

When choosing a “fun” place to stay with monorail access : choose the Contemporary.  As my second favorite hotel to stay at on site, this hotel brings a fun, modern style while keeping that magical Disney feel.  It also helps that it hosts two of my favorite “must eat” restaurants inside all of DW- California Grille and Chef Mickey’s.  More on those later….

The Contemporary: I worked at Disney circa 2000…that feels like many eons of a quadrillion moons ago. Being the crazy college kids that we were, I felt as though I got a small taste of each resort when we would go park hopping on our off days. We would occasionally stop at the resorts when we were exploring the properties.

Bringing the hubs and family back for our first official vacay, we decided to stay at the Contemporary. It was a great pick for our first time around…We had a room with two large beds, and Malone used his pack n play. (He tends to prefer that.) The monorail runs right through the hotel, and the kids LOVED that. It has two of the greatest restaurants in the entire park network. {Chef Mickey’s and California Grill.} As well as a fast service restaurant on the main floor. Win.

At night, the kids would collapse from exhaustion after their baths, and Jamin and I would get cupcakes (more on that, later) from downstairs, and sneak out onto the balcony. Disney tends to think of everything, and at night, they would have what seemed to be another version of the electric light parade on the water.

It was nice for us to wind down as well, and plan out what we wanted to hit the next day. That being said, however, I was also looking at the positives of that. The next time we do Disney in a few years, I will prefer a condo kind of set up. That way when our kids crash, we aren’t watching the football game on mute, and texting each other on our phones.

You live, you learn, but the contemporary is a great choice for your first time around. It all just depends on what you’re looking for! I think you can do something different each time, and still count it a success-every option has a set of pros and cons. I think that’s part of what makes the vacation experience so wonderful.

When on earth should our family go?

Well, my friends, that of course, is all up to you. But here’s our take on some of the best times to visit the parks:

Time of Year: I would have to say that my favorite time of year to go to Disney World is in late Fall/Winter.

Disney does everything over the top, so it is no surprise that they go extreme when a holiday is nearby. I have been during October, November, and December (as well as right around Easter) and I LOVED being there for each of the Fall/Winter months. The traffic in October has picked up a lot recently due to the Food and Wine Festival, free dining plan week, and more schools with Fall breaks.

November and December tend to be a lot slower, with the exception of the actual Holiday weeks (week of Thanksgiving and week of Christmas). Early December is magical with all of the amazing Christmas decorations and awesome weather.

Do be warned, however, that Orlando tends to get a couple of week of colder weather each Winter, and when it comes there it IS COLD. Don’t worry, though. Each store has an abundance of gloves, hats, jackets, and sweatshirts to help keep you warm.*

*Another example of tips + tricks we have planned ahead …saving money= packing your own. More on that, later. 

Spring: Expect cool mornings/nights and warm days. Crowds can be heavy with spring break and graduation trips, but the extra magic hours if you’re staying in the park, can help.

Summer: Expect hot and humid weather. Crowds are unlike any other time of year, especially major holidays (4th of July was borderline insane but fireworks were unlike anything I’ve ever witnessed) you MUST take advantage of extra magic hours and fast passes during this peak time.

Cast members go above and beyond to make wait times and the Disney experience enjoyable for everyone. Despite the heat and crowds, this is my favorite time of year to go due to the attitudes of cast members. They really make it pretty great. 

Fall: Expect hot to warm days and nights. Crowds are heavy, Fall is a peak time for International guests to visit WDW, as many countries are on break during this time. Historically WDW offers free dinning plans during fall, which offers a huge savings but also make reservations for table service meals a top priority. However, we found this season to be a more stressful environment.

Winter: Christmas! (As Cristin mentioned above) 

 Photo courtesy the ever talented Jillina

Spring: I spent an entire spring and part of the summer working in the parks. I think, just like anywhere, there will be ebbs and flows in the day to day. There were down days, and there were crazy days. Before Graduations begin, after spring breaks, are probably your best bets…if you want to be hardcore about it, you could probably do a little research, especially pertaining to the local school schedules.

The Family and I went over Labor Day weekend, and to be quite honest, will never do it again. It was over a holiday, and I think because of that, the crowds were unreal. After working there, I was spoiled: accustomed to off hours and zero wait times, so to be shoved out of the way by numerous over anxious borderline mentally unstable adults, who were a little too excited about the fantasyland carousel, while trying to navigate two strollers and three children… it was enough to push anyone over the edge.

Tuesday morning, the day after the holiday, however, things had died down again. Lines were a fifteen minute walk through wait. It may be an inconvenience with school schedules, but if you can plan to come right after a big holiday, that may be your best bet with wait times, crowds, people in general that make you want to shove them into the nearest car track, and other bad things because shove-y adults are evil and should be taught a lesson. Just sayin.

That about sums up today’s first segment of Keys to the Kingdom : How, Where + When to stay in the parks. Next week : Dining.

We hope you found some variety in our takeaways from our own experiences…But now it’s your turn. If you’ve been before, what were the pros and cons of it all, and where did you stay? And, if you have any specific questions for next week’s topic, be sure to let us know!

Thanks so much, as usual, for stopping by, and we hope you’re able to use this little series as a good resource!

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Responses to keys to the kingdom : how, where + when.

  1. Stephanie says:

    The Boardwalk is my favorite place to stay, as well! I’ve stayed off property several times, as well as at the Fort Wilderness Campsites (when my parents used to have a camper), but none of those were as good as the Boardwalk. The hotel was great, and we loved how convenient it was to Epcot.

    I’m going back to Disney World next week. It’ll be my eighth time to go and my husband’s first. He has a conference at the Disney Swan, so we’ll be staying there. I’m curious to see what it’ll be like, since it’s operated by Starwood rather than Disney.

  2. Thanks so much for this post! We want to plan a trip for our kids- 3 years and 3 months but are clueless. This is so helpful!!

  3. Kelly Weston says:

    So, random question of the day…what’s the name of the font you used for your “Keys to the Kingdom” text. It’s SO CUTE! Thanks :)

  4. Brooke says:

    Hello there!, I’m a follower of your blog but also wanted to share with you My family and I live aporx. 8 miles from the Kingdom. It’s one of our favorite places to go! (Especially during Christmas, it’s crazy busy, but oh so magical!)

    If you or any of your readers are ever in the Orlando area and looking for something to do other then Disney….. stop by It’s a comprehensive guide which includes a calendar of events for children and families in Central Florida.

  5. Hey Ashley! Your blog is so much fun! The husband and I have been to the World 7 times in our 8 years or marriage. We have a slight problem! Our favorite is Wilderness Lodge, just needs to be in the monorail loop! So easy to just load junk and kids into strollers in the hotel room and not take them out til you are parking for your first ride in the park, ya know??!

  6. stephanie says:

    We love Disney! The first time we took our kids they were 15 months and a little over 2 (13 months apart). Everyone was telling us to wait until they were older, but we were very glad that we took them when we did and couldn’t wait to go again. The kids loved it. I loved seeing the magic in their eyes. We let them nap when they wanted to, while they napped we would watch a show or chill with a treat. Our first trip was in the August heat and if you can avoid it, do. Our second trip was in June and while others were complaining of the heat, we were comparing it to horrible August, so it was not too bad to us. Each time we have gone we rented a house with a private pool 15 minute drive from Disney. The price for a week was cheaper than most hotels, so this saved a lot of money, plus you have a washer and dryer and all the other home things available which is nice when you have young kids. We would love to stay on site one day, but that will depend if our budget allows. We highly recommend rental homes and check for them over hotels in other vacation destinations. Each time we went we had a 6 bedroom home, the second time we went with friends and split the cost, which made it even cheaper.

  7. Karen S. says:

    Here’s my two cents: we stayed at Port Orleans (in the “moderate” category), and got two adjoining rooms. It was cheaper than staying in a larger resort with a suite. We could get the kids to bed early when they were tired, and we could stay up and watch movies.

  8. Holly says:

    I’ve been reading your blog for a while, but this is my first comment. This post brought me out of my lurkdom! We have just begun planning for our first family trip to disney, next fall. Your insight has been very enlightening! Everyone has an opinion on Disney, but having it all in one place , by seasoned pros is going to be great! Looking forward to your next posts!

  9. Tiffany says:

    Yeah! We are surprising our kids for Thanksgiving with a trip to Disney! So glad y’all are doing this series! Thanks for the great tips!

    • Jennifer says:

      I’m interested in knowing how your experience was during the week of Thanksgiving. Thanks.

  10. Nicole says:

    A plus to the mods over the value: queen beds! For us, when we can’t swing a deluxe, the mods always win for the bigger beds. Plus they’re closer to the Holy Grail, I mean Epcot. 😉 Boardwalk is where our heart is though.

  11. Carrie Baxter says:

    Hotel favorite for our family which isnt as expensive is Port Orleans. Riverside for older kids and French Quarter for younger kids. This twin resort has great pools, with slides. The Riverside has a live nightly piano player in the lobby who is super fun and Disney friendly. Port Orleans has the rentable boats, bikes and a boat ride to Downtown Disney. In addition, they have a fishing hut where you can rent poles and spend a lazy afternoon fishing. This is also one of the few hotels that you can fit 5 people in. They offer trundle beds in some of their rooms for the youngest child.

  12. Tanya says:

    Some money saving info to add – if you would like to stay on site in the deluxe villas (also known as Disney Vacation Club Villas) but cannot afford, or just do not want to pay, the rack rate that Disney charges look into renting points from a Disney Vacation Club (DVC) member. There are many websites which make this a very affordable option, often more affordable than a much small moderate resort room!

  13. Amy says:


    I have just read through some of your Disney world stuff, and I was wondering if you could help me. We are going in February with our 4 year old daughter. We will only be there for about 3-4 days and therefore we have to be a little selective. What parks are the best for a 4 year old girl? Of cause Magic kingdom is a must but what else?

    Thank you