1st Disney Trip Please Help Me!

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I am starting to think about planning our family’s first trip to Disney and want to make it the best trip possible. With that said, I have so many questions and ideas floating around my head so wanted to open the conversation up to my wonderful readers for suggestions.

1st Disney Trip Help Me Plan

I’m sure that you have a favorite place to stay, a favorite time of year to go or another tip or trick that makes your Disney vacations more fun! So, here is your chance to help me (and possibly other readers) plan our families first trip to Disney.

Here are some questions that I have:

  • When is the best time of year to go? Think cooler weather, less crowds, etc.
  • Where to stay? Points hotels, pay cash for Disney luxury property, rent a house on AirBNB?
  • Best parks to visit in addition to The Magic Kingdom?
  • What reservations to make for special events like breakfast with Princesses?
  • Any other Disney tips or tricks?

Please post a comment, I would love to hear what you think!

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Bottom Line

What do you think? Please help me plan our Disney trip. I am pretty good at planning adult trips to Paris, Bora Bora and the like but, when it comes to Disney; I’d love my readers help!



Editorial Note: Opinions, analyses, reviews or suggestions expressed on this site are those of the author’s alone, and have not been reviewed, approved or otherwise endorsed.

About The Weekly Flyer

The Weekly Flyer writes about travel from a business traveler perspective. He travels the world every week accumulating points and miles along the way.

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  1. I highly recommend RideMax. It’s a fantastic way to plan out each day and give you an itinerary to follow, so you can get the most out of your day. Seriously, it is totally worth it. https://ridemax.com/

  2. In Florida now; used undercovertourist.com for tickets and easywdw.com for trip planning

  3. There’s an enormous wealth of advice (and others) could give but the critical initial question is whether it is for adults only or also children and, if with kids, what ages. So much Disney advice flows from that question.

    Generally speaking in terms of time of year, the best combination of weather and crowds is often mid-September to mid-November.

  4. I go to Dinsyeland twice a year and Disneyworld 3-5 times a year and Disneyland Paris at least once a year. For Disneyworld I suggest that u go it early December and make use of the Mickey so merry Christmas party , BUY that ticket, it’s a special event and the ticket is for entry into the park from 4-midnight the best part is the regular park guest leave the park and only ppl with the special event tic are allowed in the park, making the park attendance light, think 10,000 ppl at the event rather than 50000 ppl. I usually go early April the park is usually empty before east coast kids spring break …. I love planning trips so u have my email for quesrions

  5. I would not take two kids under 4 years old to a 4-midnight event (I presume Alan wrote his email before your response about ages). I see parents dragging young kids in strollers at Disney at night and wonder how much enjoyment most kids are getting.

    At that age, take advantage of the ability to go between mid-Sept. and mid-Nov. before they become school age and you are locked into crowded periods.

    They’ll be most interested in Magic Kingdom, so I recommend staying on a monorail hotel (Contemporary, Poly, Grand Floridian) or Wilderness Lodge, although that has construction right now. Disney often offers packages during its slower periods. Alternatively, you can try to rent points from a DVC member (look on disboards.com) since that’s much better value than buying hotel rooms and can give you a lot more space with the kids.

    I’d visit all the parks, although the kids will want most of their time in MK.

    Dining reservations can be made 6 months out. Look at the options to see what your family might like. Nothing is must do. Definitely get fastpasses 60 days out to minimize lines for meeting princesses and other characters and some of the more popular rides.

  6. Disney is the one vacation spot we do with any regularity where points really do not help. We always stay on property as the advantages that affords outweigh the cost savings. We own the DVC timeshare which helps defray that. If you are set on using points for lodging, then I would stay at Swan/Dolphin (spg). It’s the only non-disney hotel within walking distance of parks (epcot & hollywood studios). You can also rent DVC points to stay in the time share for a fraction of the disney rack prices….and the rooms are nicer.

    Undercover tourist is a great choice for tickets. We use them when we are not on annual passes.

    As far as times to go, end of Jan and most of Feb (non -presidents weekend) are a great time to go. September and early October are low crowds but hot. My favorite time to go is the first 2 weeks of December. Lower crowds and decent temps…and all the Xmas decorations are up. This used to be a very slow time but is less of a secret than it used to be.

    Learn to use the fastpass system…know how saves HOURS of standing in line. Also, getting to the parks at opening is huge in saving time as well….that first 90 minutes can be a great time to get through a lot of rides while the slackers sleep in.

  7. Start with a website like touringplans dot com. Sign up for their travel planner (you can sign up for 6 months or a year). They rate every day in terms of historical crowds and break everything by park. They also have a very informative book (Unofficial Guide to Disney). As someone above mentioned, use undercover tourist to purchase tickets. If you sign up for the mousesteps newsletter she will have a special link to buy discounted tickets from undercover tourist. In terms of hotels, depending on how long you are planning to be at the park in terms of hours per day should influence your hotel choice. The cheapest way to do Disney Delux hotels is by renting Vacation Club points from someone. There are a few websites that will streamline the process. The other theme park I would recommend is Universal Studios. Again, touringplans will help you out. Best time to go would be in February but Disney is now always busy. Look at touringplans historical data to help you out.

  8. As an Orlando resident, we frequent the parks weekly. Sept. to early December is a great time as is Spring if you can avoid Spring Break timing. Also avoid other major holidays as well as anytime June – August. Animal Kingdom is a fantastic park for kids. My favorite is Epcot and if you time it in the Fall, the Food & Wine Fest is amazing fun between September and November. But likely the kids won’t find it quite as fun as adults. The majority of your time should be planned around the Magic Kingdom with a day at each of the other parks. If you stay at a resort property, they offer extra magic hours and early entry. In addition you can book your Fast Passes 60 days in advance, so plan on doing that the very second you are able to, in order to get the best rides selected. The resorts all offer so much in terms of just the ambiance, that staying at one of the properties would be my suggestion. Disney really extends the happiness to all of their touchpoints and staying at a park property just puts you so much closer to the fun. Plus those Fast Passes will help you save time once in the park…. The Mine Train in Magic Kingdom is impossible to get a Fast Pass for unless you are staying at a park resort and wait times without a pass often reach two to three hours.

    As an Orlando resident, I am happy to answer any and all questions! Be sure to book Be Our Guest at Magic Kingdom for lunch. And Earl of Sandwich at Disney Springs is one of my favorites if you want to wander the Springs for some shopping or dining. I also love Mexico and Paris for Epcot dining choices.

    Of the resorts, my brother visits often and he usually picks Pop Century or Allstar Sports as they are relatively inexpensive. But if you want a treat I’d pick Animal Kingdom Lodge for the cool added amenity of the 30 species of African animals that roam the property grounds. And their pools are pretty darn cool too. Kidani Village, the newer building, is my favorite. The campground is also a thought on places to stay if you are up for that. At Christmas time, the campers in RVs get pretty darn crazy with the amazing decorations that are a must-see.

  9. I agree with the “Be Our Guest” at the Magic Kingdom for a meal, the pork was wonderful and try the grey stuff, it’s delicious…. Be sure to check out all the rooms if you are Beast fan. Off Property, we stayed at the B Hotel and could see the fireworks from our room, and used our travelocity points and a coupon for it.

  10. February (non holiday weekend), September (after Labor Day), and early December are some of the least busy (relatively) times to go. I think if you really want to enjoy the resort as an adult, go during the Food and Wine Festival (late Sept to early Nov). If you can go after Halloween, the festival goes for another 10 days or so and you can catch some of the holiday decorations.
    I’d recommend to anyone going to try to get a 1 bedroom DVC villa at Bay Lake Tower (BLT) (great location) or Animal Kingdom Lodge (AKL) if they can afford it (rent points – many sites). These 1 BR units are the only ones on property with 2 bathrooms. Beach Club and Boardwalk Villas also are great locations, especially for activities outside the parks.
    Even though they have free transportation from the airport, and the on property transportation is improving, I say get a rental car. There are a plenty of things to do/see just outside the property, and if you don’t have a car they can get expensive.
    Dining on property has gotten very pricey, but I still go to the breakfast buffet at Boma (AKL) every trip. I would say AKL has the best dining options on property in one place. No matter what, do not get any dining plan.

  11. 1st- Take out a second mortgage on your house. Everything about Disney is outrageously expensive.

    2nd- Unless you can handle oppressive heat, travel between November and April. Orlando is extremely hot during the summer, the humidity is always close to 100%.

    If you want to eat inside the parks, make your reservations a year in advance. Unless you book far ahead, most likely you will not get into any of the decent dining facilities.

    Best in-park hotel options, in my opinion, are the ones served directly by the monorail. You can get in, and more importantly, out of the parks quickly.

  12. When is the best time of year to go? Think cooler weather, less crowds, etc.

    October is a nice time to go. You can check out the Halloween party then too. Make use of the crowd calendar at Undercover tourist. Weekends should be avoided as much as possible because of the locals showing up. We try to time our stay so we are arriving or leaving on a Sat or Sun or do something else that day.

    Where to stay? Points hotels, pay cash for Disney luxury property, rent a house on AirBNB?

    A few years ago we used to stay at the Holiday Inn or Hilton near downtown disney. You can walk to downtown disney and the hotels there have a shuttle that takes you to the parks. However, Disney has gotten a lot busier and we don’t find the savings worth it to use but obviously everyone has their own priorities. The Dolphin and Swan are run by Sheraton. You dont get the Magical Express from the airport but you get to ride the Disney buses on property. Also you can walk to Epcot and Hollywood Studios. You do have to pay for parking and there is a resort fee so factor that in. Renting a condo is only worth IMO if you have a larger family but again depends on your budget. You can certainly save money.

    Best parks to visit in addition to The Magic Kingdom?

    MK, Epcot, AK, HS is how I would rank them. If you have time take a day to go to Universal. Their parks are well worth seeing as well.

    What reservations to make for special events like breakfast with Princesses?

    Magic Kingdom – Royal Table for princesses, Crystal Palace for Pooh and friends(and has a nice buffet), Be our Guest(lunch is quick service no characters, dinner has the Beast).

    If you go to Disney site you can see all the character dining and decide which your kids are interested in. Royal Table, Be our Guest and Askerhaus fill up very quickly.

    Any other Disney tips or tricks?

    Show up early. MK opens actually 20 minutes before stated time. They have a short opening ceremony and then let everyone in and then open rides at appointed time. Also most people don’t drag themselves in until about 2 hours after opening. You will get the most done in morning or late in evening. Depending on day it may be worth to do breakfast at Crystal Palace if you can get the opening slot at 8am. If park doesnt open until 9am that day(no extra Magic hours) then you can enter park with very few people around since only tours and people with breakfast reservations are allowed in. Good time for photos or eat quick and beat everyone to the rides.

    Reservations for dining open 180 days for people on disney property. You can book for whole stay starting 180 days from first day of your stay so potentially you can book 190 days out. You should book on very first hour of very first day for popular restaurants. If you miss out do not despair keep trying every day. Openings come up as people make changes but save yourself a headache and reserve early.

    If you stay on property you can do fastpasses you can do this 60 days out otherwise 30. Again do this immediately. Schedule them for early times as possible as you can add on to it(availability permitting) once you use up fast passes and you can go to kiosk in park to add another.

    There are obviously lots of sites devoted to all things disney full of tips, tricks and hacks.

  13. When is the best time of year to go? Think cooler weather, less crowds, etc.
    –I like October (Food and Wine Festival) if you can avoid going to epcot on a weekend. January will be slow and good prices but some rides will be closed. First week of May is usually really nice too (Flower and Garden Festival) but getting towards the warmer side.

    Where to stay? Points hotels, pay cash for Disney luxury property, rent a house on AirBNB?
    –Everyone will have a different opinion on this. If you have SPG points to spare, Swan and Dolphin have a great location. I wouldn’t waste my SPG points at Disney. I would either stay at a value resort on property (All-Stars, Pop Century, Art of Animation) or rent someone’s Disney Vacation Club points to stay at a deluxe level resort. Offsite will be cheapest but you will have to add in the cost of renting a car and paying for parking. I hate driving in Disney so I’d rather stay on site.

    Best parks to visit in addition to The Magic Kingdom?
    –All are great, but if you had to skip one, skip Hollywood Studios due to construction. Epcot is my favorite.

    What reservations to make for special events like breakfast with Princesses?
    –You can go overboard with this. I would just do one. Your time is better spent at the park or relaxing at the pool. If your kids have a must see character, choose a breakfast with them so you don’t have to wait in line to meet them later.

    Any other Disney tips or tricks?
    –A million tips that can get overwhelming. Two things above all else. Get to the park when it opens and go to the busiest attractions first. If you don’t get to the park until 10-11 in the morning, you will be waiting in line all day for rides. If you get there at opening, you can be done most of the park by noon (except magic kingdom which is really more of a 2-day park).

  14. When is the best time of year to go? Think cooler weather, less crowds, etc.
    – I think October – January (other than the holiday week) is the best. You can take advantage of the Food and Wine Festival through mid-November and the various special holiday parties. Christmas decorations start early November

    Where to stay? Points hotels, pay cash for Disney luxury property, rent a house on AirBNB?
    – Really depends what you want and how many of you there are. If you’re going to be spending a lot of time at the resort you may want to stay at one of the nicer hotels. If you’ll be out all day and the hotel is a place to sleep why waste money on it. My biggest tip is check out Wyndham Bonnet Creek and buy through Vacation Strategy or one of the other places that rent out the time shares. I’ve gotten a gorgeous 2-bedroom with full living room, kitchen in a nice resort for $700-800 for the week!

    Best parks to visit in addition to The Magic Kingdom?
    All of them – seriously . . . things to do in each but you have to do some research depending on what you want to do and what you don’t like. But no park is worth skipping completely.

    What reservations to make for special events like breakfast with Princesses?
    Make reservations as soon as you can when you hit 180 days since the best ones go fast. Go to one of the many disney boards (the DIS is my favorite) and read what people are saying. Character meals book early. Some of my favorites are breakfast at Crystal Palace (Pooh) or Tusker House (Mickey/Minnie/Goofy/Donald). If you like Princesses – Akershus at Norway and the Castle Dinner are great (but expensive for Norway and EXPENSIVE for the castle).

    Any other Disney tips or tricks?
    On the boards read up on FastPass and the best rides to use them on. You want to use them for the rides you’d expect to have the longest waits. I suggest either making them for starting at about 11am (since the first hour of two in the park lines are pretty good) or if you’re hopping use them for the 2nd park you’re going to.

  15. I lived here for the last 12 years I can give you my advice on the questions. also been an Annual Passholder for the last 10.
    Best time of year
    The 2 times of the year to go as far as crowds are February and September. Nobody is on spring break the lines are shorter and you can actually go to attractions. Fast passes are easy to get and if you are booking on property you can get them MONTHS in advance.
    Where to stay
    I would stay at the Starwood properties onsite. They give you points. The dolphin and swan come to mine which are rebranded Westin and Sheraton hotels. You can walk everywhere and the price isnt too bad. Also You can use the magic band and get charges sent to the room. Doing this too you can actually accumulate star points on your whole trip and combine to get a ton of points. If you dont care about points the four seasons is awesome also great lazy river and amenities.Somewhere in between is the boardwalk hotel (in the center of everything) (even though four seasons might be cheaper).

    If you are into harry potter universal has enough for maybe a 1 day 2 park hopper you want to take the train that runs in between parks its one of the better experiences of the universal/islands of adventure area.

    Epcot is awesome too I love going there.. the less visited one of all of them I think is Animal Kingdom.. but the zoo is pretty awesome… I am a big disney fan so feel free to ask me questions.

  16. Step #1: Subscribe to touringplans.com. You can look at crowd calendars + they have great plans that give you an order in which to ride. It can save you a ton of line waiting time! They also have a ticket finder function that helps you find the cheapest tickets. For your first trip, buy a 5 day pass and go to all 4 parks (5th day is usually free). No need for a park “hopper:” on your first trip. Stay a minimum of 5, but preferably 6 or 7 nights if you can.

    Step #2 – lodging: Consider renting from a Disney Vacation Club member. This will allow you to stay on property at nice villas close to parks at about half the normal cost (plus being on property gives you early/late access + free airport transportation). Go to Disboards.com and look for DVC rent/trade forum. My favorite is Beach Club Villas (fab location); a close 2nd is Animal Kindom Villas (Jambo house first then Kidani) for the awesome animal viewing.

    Also note: Swan/Dolphin are good options too (although no free airport transportation). THE SWAN IS A WESTIN PROPERTY, so you might be able to do the points thing.

    Step #3: Book dining 6 months in advance. If you want Be Our Guest at Magic Kindgom, book it first and book it for the last night of your stay to increase your chances of getting a res.

    Step #4: Look for discount Disney gift cards. Either purchase at Kroger during 4x fuel points or buy from Target with Red Card Discount. Or use Amex offers (current Rite Aid offer works). These can be used for your park tickets and dining (and lodging if not renting DVC).

    Step #5 – important: Make sure to reserve Fast Passes 60 days in advance if staying on site (30 days off site). The good rides sell out, which is unfortunate.

    Regarding food, we keep breakfast items in the room and take backpacks with sandwiches/chips/fruit for lunch. Then we splurge for a nice sit down dinner. Food prices are insanely high. We like all restaurants at Animal Kingdom resort + Flying Fish on the Boardwalk + California Grill at the Contemporary. The food at Epcot is generally great!

    At Hollywood Studios, do dinner/show package for preferential seating to Fantasmic (plus you avoid the line). Great show – don’t miss it.

    I could go on and on and on . . .

  17. Here’s my two cents worth of advice coming from an annual passholder.

    Best time to go is September. Weather is great and school age kids are in school, so crowds are definitely smaller. Downside to that though is the parks will also close earlier. If Disney Halloween or Christmas festivities or Disney Food and Wine Festival might be of interest…travel October through mid December, avoiding holiday periods. They are all fun, unique to their specific times of the year and crowds are still manageable.

    Where to stay..our preference is The Beach Club, but all the resorts in the Epcot area work quite nicely. You can easily walk to Epcot and Hollywood Studios which mean way less time waiting for and riding buses. The resorts there have restaurants, child care, pools, etc. and the Boardwalk area is an easy walk around the lake. From the Boardwalk resort, well it’s right there.

    As to tickets, I would agree with other posts here that Undercover Tourist is a good place to get tickets ahead of time. However is you are going to stay on site at any of the Disney resorts, you might want to consider buying one annual pass for yourself. While it’s more expensive that buying a ticket, it can get you up to 40% on Disney resort reservations, as well as other amenity discounts. If you were to make a second trip within a year, the extra cost of the pass would be the same as buying a ticket for the second trip. However that 40% off room rates can be huge, especially if staying at the higher priced Disney resorts.

    As for character dining I would recommend 1900 Park Fare at the Grand Floridian Resort. The characters at dinner are Cinderella, Prince Charming, along with Cinderella’s stepmother and sisters. The characters have been enjoyable when we have been there and as the meal is a buffet, it’s not terribly over priced compared to some of the other character dinners can be. Another suggestion is breakfast at the Crystal Palace. If you can get a reservation before the park opens, such as 8ish in the morning, you’re actually in the Magic Kingdom before it opens. It’s great for some photos along Main Street as there is no crowd. After eating you can wait for the crowd to come into the park or walk back towards the train station to watch the park opening show from inside the Magic Kingdom, rather than out with the crowd.

    For rides…use the fast pass system for what you really want to ride. Again, staying on site assists with getting first selections for Fast Pass and earlier restaurant reservation selections, as well as extra park hours options. To specific rides, the kids will probably help you decide that. Just don’t try to do everything in a day.Go back to the hotel to swim, relax and unwind some and then return to the parks in the evening for the lights and fireworks.

  18. Staples has Disney Gift Cards that can be purchased for 5x rewards with Ink. These can be applied to ticket purchases.

  19. Perfect ages! To use points stay at Hilton Bonnet Creek…best pool around with lazy river, close by, and free shuttle to the park. Also kids eat free. Oct or late Jan early Feb are nice times to go with fewer crowds and typically nice weather. On property we like Contemporary if you can find a good package deal…often they will do free dining (totally worth it for thedining plan) or discounted rooms during this time especially if you buy an annual pass (which is worth it if you are staying over like five days or going back within a year). Absolutely must make dining reservations in advance or you won’t get to eat where you want when you want. Crystal Palace for breakfast is still our favorite even though kids are 12-13 now instead of 2-3. Chef Mickeys is a great one too for any meal but dinner is our favorite. Lots of good websites for touring plans and advice on fast passes. Mousesavers is one of my favorites along with wdwinfo

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