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5 Experiences You’ll Regret Not Trying When Disney World Reopens

We sure are missing the Disney Parks right now, and there are some things that we really hope we’ll get to do when they reopen.

Happily Ever After

With so many wonderful ways to enjoy Walt Disney World, it’s impossible to do it all. But whether you’ve been to the World dozens of times or you’re planning a once-in-a-lifetime trip, we don’t want you to finish your trip with any regrets. Here are five Walt Disney World experiences you’ll regret not trying.

Asking a Cast Member for Their Recommendation

If you’re here, then that means that you know to turn to the experts when looking for suggestions about your Disney trip. But there are some experts you might be overlooking, and their input can make a big difference to your trip. We’re talking about Cast Members!

Walt Disney World Cast Member

Who is MORE expert than the Cast Members who bring magic to Disney guests day in and day out? Not only are Cast Members a big piece of what makes Disney World go ’round, but they are also an excellent resource for recommendations once you’re on your trip!

Le Petit Cafe Cast Members

If you’re ever on the fence about something — where to eat, what to do next, etc. — ask a Cast Member! They’ll offer their personal preferences and pieces of advice that may be super surprising and can make for an awesome twist to your Disney day. We’re not just talking about the Cast Members in the lobby of your resort hotel either. Talk to your waitstaff, attractions attendants, and custodial staff for tips!

If they have that telltale oval name tag on, chances are they can offer advice on just about any question you may have!

Cast Member

Want some ideas about what to ask? Take the risk and have the Cast Member choose for you what to order when you’re dining! We do this a lot since the Cast knows the menu at their dining location better than anyone else.

We also recommend asking for their take on what you should do on your resort day (since you might get some ideas you would have missed out on) and for their favorite attractions and tips!

Click here to watch a video on some WEIRD rituals the Disney World Cast has! 

Dining with an Imagineer

If you’re like us, you’re still thinking of things you wish you would have done when you COULD go to Disney. Maybe one of those things is a super fancy dining experience? It’s probably not surprising that that’s DEFINITELY on the list for us! Though we love fancy meals like the Chef’s Table at Victoria & Albert’s, we’re thinking something a little more unique today!

Grand Floridian Lobby

Did you know you can dine with a Disney Imagineer in Disney World? These are the folks who come up with all of the crazy tech, beautiful designs, and awesome experiences that we take part in every day we’re in Disney. The Dine with an Imagineer offering allows you to sit down with one of these super bright minds, pick their brain, and enjoy a delicious meal!

Our Dine with an Imagineer Table — Our Imagineer is sitting at the middle right

This offering is usually available at Citricos at Disney’s Grand Floridian Resort and Spa for up to 11 guests. You can typically book this experience on the first Thursday of every month at 5:30PM for $97.98 (tax and gratuity included). And you can pay an extra  $30 if you want to add the optional wine pairing. A four-course meal and a casual chat with an Imagineer? Yes, please!

You can also enjoy this experience at The Hollywood Brown Derby in Hollywood Studios. You can typically book this version of the experience on Mondays, Wednesdays, and Fridays at 12PM for $89.46. Remember, park admission is required and not included in this option!

Hollywood Brown Derby

This truly is a bucket list experience and we definitely wish we could take advantage of it right now. If you’re planning a trip for when the parks reopen, you can book this experience online or by calling (407) WDW-DINE. Remember guests must be 14 years or older to attend.

Note that Dine with an Imagineer won’t be available immediately when the parks reopen, but we’ll let you know when it’s back!

We reviewed Dine with an Imagineer! Click here to check it out!

Getting a Professional, Personal Photopass Session

Maybe you haven’t thought of this one yet, but you definitely should have it on your radar! Photopass and Memory Maker are great ways to get photos while you’re in the parks, but did you know that you can upgrade to a professional, and personal Photopass session?

PhotoPass outside of Tower of Terror in Hollywood Studios

There are even a few different options for photoshoots so that you can pick one that fits your needs and your budget! Back in February, Disney released the new Capture Your Moment photo sessions in Magic Kingdom for $50. These sessions get you and your fam a 20-minute shoot to help commemorate celebrations and milestones during regular park hours. Neat! You can book Capture Your Moment by calling 407-939-7758.


Guests can also opt to use Disney Fine Art Photography! This service is a little bit more on the pricy side but there are more options to choose from. Depending on your package, these sessions could incorporate lighting, staging, and other techniques.

Pricing ranges from $225 for a Mini Portrait Session at a Resort to $1,999+ for a private, 5-location family portrait session in Magic Kingdom before the park opens. Book these experiences by calling (407) 934-4004.


Making memories with the family is such a cherished thing and we’re missing Disney memories more than ever right now. When we get back to the parks, we’ll definitely be looking for the best ways to capture the memories, and these shoots are a great option!

Click here to learn all you need to know about the Capture Your Moment sessions!

Doing a Food or Drink Crawl

Our next suggestion is one that’s near and dear to our hearts. You’ve just gotta do a Disney food or drink crawl when you’re on your next trip — ESPECIALLY if you’ve never done one before! And, hey, if you have done one before, we say it’s time to embark on another!

Disney’s Contemporary Resort with Monorail Access to Magic Kingdom and Epcot

Food and drink crawls are a great way to experience some menu items and dining locations that you might otherwise miss out on. Our DFB crawls are crafted SPECIFICALLY so that you chow down on the best of the best and check out some awesome locations along the way.

Baymax Cupcake

Consider trying a transportation-based crawl like the Skyliner Pub Crawl, with tasty libations from Hollywood Studios to Disney’s Caribbean Beach Resort. Or try the Monorail Crawl for eats from Disney’s Polynesian Village Resort to Disney’s Grand Floridian Resort and Spa!

Disney Skyliner

There are other crawls, too! One of our most FAMOUS crawls is the Cupcake Crawl and we can also recommend the Epcot Classics Snack Crawl! Whatever crawl you choose to tackle, you’re sure to have a fun time AND try some new things!

Click here to learn more about the Skyliner Pub Crawl!

Asking for the Best Seat on a Roller Coaster

Last, but certainly not least, we have a fairly simple idea that a LOT of guests have never thought about before! It’s easy, and you’ll regret NOT doing it once you know it’s a thing! You may want to request the best seat on a roller coaster!

Rock ‘n’ Roller Coaster Starring Aerosmith

Whatever your favorite coaster in the park — be it Space Mountain, Rock ‘n’ Roller Coaster, Seven Dwarfs Mine Train, or Slinky Dog Dash — there’s a seat that will make the ride a little more fun for you! This is an easy trick that can seriously perfect your ride experience.

Space Mountain

Okay, here’s the tip: If you’re looking for a smoother ride with great views, request a seat in the front. Want a more thrilling and all-around WILDER ride? Ask a Cast Member to seat you in the very BACK of the coaster! Thanks to SCIENCE, the front gets the slowest, smoothest ride while the back gets whipped around from the pull of the rest of the train!

Slinky Dog in Toy Story Land

Take it from us, there’s nothing quite like a ride in the very back on Big Thunder Mountain. If you’re a thrill-seeker, this can really make the difference between a good ride and a GREAT one!

Big Thunder Mountain in Disney World

And that’s all we wrote! Avoid those regrets by trying out these Disney experiences when you get back to Disney World. Most of these are small, some don’t cost a penny, and they’re all uniquely Disney. They really are a blast! Check out our DFB Video below for even more tips for your next trip.

What’s one thing you regret not doing on a Walt Disney World vacation, and what’s your advice to help others avoid it? Let us know in the comments!

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Filed Under: Disney Entertainment, disney parks, disney resorts, Featured, Walt Disney World, capture your moment, cast member, Cast Member Recommendation, Citricos, dining with an imagineer, Disney Crawl, Disney Fine Art Photography, disney planning, disney regret, disney regrets, Disney World, Drink Crawl, Food Crawl, Hollywood Brown Derby, Memory Maker, PhotoPass, rollercoaster, Rollercoaster tips, Snack Crawl